Historical Streets

  • The New Canaan Historical Society has partnered with the NewCanaanite.com on a digital Street Names Database that lets visitors look up the origins of local street names online.

    With information drawn from a 1960 annual of the member-supported Historical Society, the searchable database is a drop-down menu that captures information on how New Canaan street names got their names, in a snapshot from that year.

    As a Society, we have taken the further step of building out a completely updated list—should residents seek information that’s missing from the database (such as more modern street names) or want to review in greater detail what’s included in it—and that’s all available in the organization’s research library at our 13 Oenoke Ridge Road location.

  • Apple Tree Lane

    A dead-end spur from Turtleback southward toward West Road, was built about 1956 for the old apple orchard through which it runs. (Source: New Canaan Historical Society)


    Bald Hill Road

    Running northward from North Wilton Road into Vista near the Wilton line at the northeast corner of New Canaan, is an old road using an old name. It may be the road the Town ordered laid out into New York State in 1829, but the original highway probably is much older than 1829. (See under North Wilton Road.) Prosaic people, the early settlers named any treeless hill Bald Hill, and the name appears in the land records of many towns. On the Stamford side of Canaan Parish, the Bald Hills were those hills in the northwest corner of present New Canaan west of the East Branch of the Rippowam River. (Source: New Canaan Historical Society)


    Bald Hill Road South

    Running southward from North Wilton Road to Benedict Hill Road, is neither a continuation of Bald Hill Road nor is it as old a road, being a later hook-up between existing roads. Until the 1930s it was known as Griebel Road, named for a family which settled in the area about the turn of the century. (Source: New Canaan Historical Society)


    Baldwin Avenue

    A north-south crossroad between East Avenue and Locust Avenue, was opened up as a street some time before 1915. Before that, land along its east side was known as 'Baldwin's Lot,' where itinerant circuses pitched their tents, while farther eastward was Ruscoe's Pond, a shallow lake where ice was cut and people skated. Baldwin Avenue has also been known as 'Baldwin Place.' It took its name from John Baldwin, a harnessmaker, whose house still stands on the northeast corner of Baldwin and East Avenues. His daughter Ann Eliza Baldwin was a New Canaan schoolteacher. (Source: New Canaan Historical Society)


    Bank Street

    Running west from South Avenue, terminates at the intersection of Park Street and Old Stamford Road where the Perambulation Line, dividing Stamford and Norwalk (http://newcanaanite.com/?p=1112), crossed. Bank Street was laid out in July 1885 by B.F. Hathaway of Stamford through property then owned by the First National Bank—hence the name. (Source: New Canaan Historical Society)


    Barnegat Road

    Running northward into New York State from Pinney (Pound Ridge) Road opposite the end of West Road, originally was the northern end of West Road (which see). Consequently it was an old highway. For years the intersection of Pinney Road with West and Barnegat Roads has been called 'Selleck's Corners,' and Barnegat Road was for a time called 'Selleck Avenue.' Its present name was not adopted until the 1920's and is a mystery. (Source: New Canaan Historical Society)


    Bayberry Road

    Dead-ending northward from Wahackme not far west of Weed Street, was opened in the late 1940's. The late Calvin Kiessling and Robert G. Roles named the road for the many bayberry bushes they encountered when laying out its route. (Source: New Canaan Historical Society)


    Beech Road

    Paralleling Carter Street, runs north and south between Dabney Road and Cedar Street along old Silvermine Hill. Put through in 1956, it was named for trees along the road. (Source: New Canaan Historical Society)


    Benedict Hill Road

    Running east from Valley Road to Cheese Spring Road, is an old cross road that for years was nearly impassible. In 1904, six years after Susan Anderson (see Cheese Spring Road) was murdered by her hired man, Arthur L. Benedict bought the Anderson farm and moved there, despite the horrified protests of his East Avenue neighbors. The Anderson farmhouse faced Cheese Spring Road not far from the Southeastern corner of the cross road that took the courageous Mr. Benedict's name. The names Benedict Hill and Benedict Ridge were often used in the earliest days of Canaan Parish to designate the crest of Brushy Ridge considerably south of the present Benedict Hill. (Source: New Canaan Historical Society)


    Betsy's Lane

    Dead-ending southward from Buttery Road across the town line into Norwalk, was built in about 1957 and named for the contractor's daughter. (Source: New Canaan Historical Society)


    Beverly Hill Road

    A private road dead-ending eastward from Smith Ridge near the New York State line, does not appear on town maps. It was built in 1958 and named for Beverly Tiani, whose father, Anthony, built the first house on the road. (Source: New Canaan Historical Society)


    Bickford Lane

    Running west from lower Weed Street and then turning south to a dead end, was named for Edgar T. Bickford of Millport Avenue, the engineer who laid out the road for developing the company in 1956-58. (Source: New Canaan Historical Society)


    Birchwood Avenue

    Running eastward from Old Kings Highway (No. 1) off Old Norwalk Road, merges into Cecil Place. It was built about 1950 and named for the birch trees. (Source: New Canaan Historical Society)


    Bob's Hill Lane

    Dead-ending northward from Evergreen Road, it is a current 1960 development. (Source: New Canaan Historical Society)


    Bowery Road

    Running northward from Pinney (Pound Ridge) Road a few rods west of the end of Oenoke Ridge, passes along the end of Mud Pond and extends into New York State. It seems to have developed from a driftway leading in the 1700's to the mills along the near-by stream, but no explanation of its name is satisfactory. Many years ago, before Bowery Road was used as a name, the entire region was known as "The Bowery." In colonial days a well-known tavern was situated on the road, half in Connecticut and half in New York, so liquor was easily shifted from one state to the other if inspectors arrived inconveniently. One published "recollection" insists the entire neighborhood was like "a bower," but this does not explain "The Bowery." Others recall that the neighborhood became unsavory because of an illegal still, and still think the road was named because conditions there resembled New York City's Bowery. But the still was much later and not near the old tavern. Unraveling the history of this name is a project for someone. (Source: New Canaan Historical Society)


    Braeburn Drive

    (One word, not Brae Burn, according to Town officials), dead-ending eastward from Cedar Lane, is a 1960 development on old Silvermine Hill. (Source: New Canaan Historical Society)


    Bridle Path Lane

    Was begun in 1953 at the Dogwood Lane end and extended southward as far as Llewellyn Drive near Frogtown Road in 1959. It was named for the bridle path maintained by Ox Ridge Hunt Club for a number of years through Kelly's Woods. Many a resident strolled through these woods to one or more of the rustic summerhouses maintained there by the late Richard B. Kelly of Weed Street. It was near the northernmost summerhouse, not far from Wahackme Road, that the corpse of an unidentified woman was found in the 1920's -- constituting New Canaan's only unsolved modern murder. (Source: New Canaan Historical Society)


    Brinckerhoff Avenue

    Dead-ending southward from Bank Street, with Lockwood and Mortimer streets, comprised Prospect Heights, New Canaan's first full-fledged real estate development begun in 1915. Frank B. Gurley of Stamford, the developer, named Brinckerhoff Avenue for the late Judge James E. Brinckerhoff of New Canaan, then a partner in the Stamford law firm of Curtis Brinckerhoff & Barrett, Mr. Gurley's advisers; Mortimer Street for Judge Brinckerhoff's secretary, Miss Gladys Mortimer of Old Greenwich, and Lockwood Street for the late Judge Charles Lockwood of Stamford, then a partner in Cummings & Lockwood. (Source: New Canaan Historical Society)


    Briscoe Road

    Running north from North Wilton Road into East Street in Vista, was named for Carrie Northrop Briscoe, daughter of Sturges Northrop, who in mid-nineteenth century purchased the old Richard's farm on Bartlett's Ridge, along which Briscoe Road runs. Even before the road was opened in 1937, the path up the ridge was known as Briscoe path; possibly it follows the route of an earlier highway. (Source: New Canaan Historical Society)


    Brook Street

    Is probably New Canaan's shortest street. All road signs to the contrary, Brook Street runs east from Summer Street across Five Mile River to meet Ledge Avenue a few feet away. Brook Street, Hillside Avenue, Ledge Avenue, and Urban Street were laid out in 1913 to comprise Brookwood Park, a fanshape development east of Summer Street and south of Brushy Ridge Road and Locust Avenue. It was considerable disrupted when New Norwalk Road (Route 123) was run through it in the 1930's. In early days, before 1875, Seminary Street was called Brook Street. (Source: New Canaan Historical Society)


    Brooks Road

    Dead-ending westward from South Avenue, was begun in 1940 just south of the Sanatorium on South Avenue of the late Dr. M. J. Brooks, long-time physician and health officer of New Canaan. (Source: New Canaan Historical Society)


    Brookside Road

    Running southwest from White Oak Shade Road, south of the Merritt Parkway to Darien, was laid out in 1699 and recorded in the Norwalk records in 1700. However, in 1826 the Town of New Canaan on request met with Darien and Norwalk officials ran the New Canaan piece of the road again. The road appears as Darien Road in the 1888 New Canaan Directory, and from 1920 to 1957 it was called Gracie Road. The "brook" in question is the Goodwives River, which figures prominently in the boundary disputes between Stamford and Norwalk until 1673 and in land disputes until 1717. (Source: New Canaan Historical Society)


    Brushy Ridge Road

    Now winding eastward from Locust Avenue just east of New Norwalk Road to the top of Canoe Hill, is a part of an important old road from Norwalk that followed the Silvermine Road up the valley, tuned westward where Valley Road now begins, to go up Canoe Hill and across Brushy Ridge. Laid out six rods wide (later cut to four) before 1728, the Brushy Ridge path to the Meeting-house continued along present Locust Avenue and up Main Street to the first Congregational Church. Another branch turned northward to follow present Garibaldi Lane and go up what is now called Old Kings Highway (No. 2). The Brushy Ridge Path to the Meeting-house was one of the five road radiating from the church in the early days. At times the road shows up on land maps as Brush Ridge Road. The hill section has figured prominently in land records as a landmark, being known as Benedict Hill (for the earliest land-owners), Lockwood's Hill, Downey's Hill, and Fischers Hill. The hill appears as Mount Prospect on the 1867 map as the Mount Lebanon on the map of 1878. In the 1860's Dr. WIlliam Thompson, a former missionary and author of a three-volume history of the Holy Land, built a house on the south side of the road and landscaped his grounds with cedars of Lebanon. His estate, known as Rock Side, was open to New Canaanites, who passed through the stone gateway still standing near the sharp turn in Brushy Ridge Road, and in 1877 the New Canaan Messenger urged everyone to go there to enjoy the views. (Source: New Canaan Historical Society)


    Burtis Avenue

    Looping eastward from Main Street to East Avenue began in the 1870's as a dead-end road named Burtis Street for the family whose house was located near the turn in the present road. Later the road was opened up to East Avenue opposite Baldwin Avenue. (Source: New Canaan Historical Society)


    Buttery Road

    Winding eastward from Carter Street to end at Comstock Hill Avenue in the Norwalk part of Silvermine, was laid out about 1720-25. When Canaan Parish was formed in May 1731, a part of the road became the Parish's boundary line. The sharp curve in the road near its western end was deliberately created when the road was laid out to preserve a spring "for man and beast," but there is no truth to the story that the road name resulted when neighbors stored butter in the spring in the summertime. The road was named for the Buttery family, long residents of Silvermine. (Source: New Canaan Historical Society)


    Canaan Lane

    A miniscule private dead-end road running southward from Hampton Lane, was opened up about 1952. But the region known as Canaan, from which came the names Canaan Parish and New Canaan, was not in this vicinity. Canaan originally was applied to that section of land that extends from upper Oenoke Ridge (Canaan Ridge) westward across West Road, which as an old highway was called "the road up Canaan." (Source: New Canaan Historical Society)


    Canaan Parish Lane

    A private road dead-ending northeastward from Mariomi Road, was so named by its residents in 1956. (Source: New Canaan Historical Society)


    Candlestick Lane

    A private road dead-ending southwestward from Father Peter's Lane, was built in 1956 and named by its residents. (Source: New Canaan Historical Society)


    Canoe Hill Road

    Runs west from the intersection of the north end of Carter Street and Silvermine Road and then winds northwestward to Smith Ridge near Country Club Road. The lower section of the road, going up the hill to join after the Civil War known as Lockwood Street, again taking the name of several families who lived along its route. Legend has always held that Canoe Hill, a name appearing in the early land records, was so named because of the canoe that Indians had built and left on the hill. There is no god reason to doubt legend in this instance, because a sizeable Indian canoe found in Ridgefield was preserved for years and may still be in existence. Indians did build them far from navigable waters wherever they found suitable trees. (Source: New Canaan Historical Society)


    Carter Street

    Now runs from New Norwalk Road (near Exit 38 on the Merritt Parkway) along Upper Clapboard Hills to meet Silvermine Road at the foot of Canoe Hill. Sometime before 1720 the road was begun as a continuation of the Clapboard Hill Path that is now Ponus Avenue in Norwalk. Running along the top of the Upper Clapboard Hills it turned westward down present-day Clapboard Hill Road, past the mill pond and up present East Avenue, being known after 1732 as "ye Clapboard Hill Path to ye meeting-house." The section of the present road, from Clapboard Hill to Silvermine Road, was laid out much later. Not until about the end of the nineteenth century was the road name changed to Carter Street, through the influence of the D.A.R., in order to honor Capt. John Carter of the 9th Co., 9th Regiment, Connecticut Militia. The Carter family were among the first landowners on the road. (Source: New Canaan Historical Society)


    Cascade Road

    Running westward from Ponus Street into North Stamford, is an old road that was laid out about 1762 from Ponus Ridge to the mill that stood on the bank of the Mill River, now called the Rippowam River. In 1826 the Town extended the road "near Cooke's mill" to the Stamford line. Any earlier name for this highway had been lost in history. The present name comes from the little Rippowam cascade that was the subject of at last two early postcards. (Source: New Canaan Historical Society)


    Cecil Place

    Running northward from Old Norwalk Road to connect with Birchwood Avenue, was built in 1947 and named for Cecil Spooner (Mrs. Robert K. Blaney), an actress whose family home was on the northeast corner of the Old Norwalk Road-Main Street intersection. (Source: New Canaan Historical Society)


    Cedar Lane

    Curving east and then south from Hickory Lane to Buttery Road, was developed during 1953-56 along old Silvermine Hill and named for the field of cedars that had been planted there by The Hoyt Nursery. Cedars were and are rare in this part of Connecticut. (Source: New Canaan Historical Society)


    Charles Place

    A priavate road dead-ending eastward from River Street near the upper end of the Upper Mill Pond, was developed in 1928 by the late Charles Meade, for whom it is named. (Source: New Canaan Historical Society)


    Charter Oak Drive

    Dead-ending eastward from South Avenue south of the Merritt Parkway, was a 1955-57 development. The Charter Oak, of course, stood near Hartford, but the road name was submitted as an entry in the contest to name Conrad Road and then used for this road farther south. (Source: New Canaan Historical Society)


    Cheese Spring Road

    Today is the upper end of Mariomi Road, passing the eastern end of Benedict Hill Road and continuing into Wilton. Just what its original layout was is something of a mystery, but the highway terminated somewhere on Valley Road. Perhaps the earliest reference to it is in a 1739 deed that transferred ownership of twenty-eight acres of land on "the north end of Cheese Spring Road in ye Huckleberry Hills" bounded on the east by "a highway." Cheese Spring Ridge seems to be a name that originated in Wilton in the 1700's, and Cheese Spring Book, which arises in a Wilton spring, was named long before the road. The story that the brook was named for cheese cooled in its waters is plain fancy. The road certainly was called Cheese Spring Road in 1897 when Mrs. Susan Anderson took a lawsuit to the Connecticut Superior Court of Errors to force the selectmen to reopen the lower road section, by then impassable, to Valley Road so she could drive to New Canaan to shop rather than going up the road to Wilton. Mrs. Anderson lived a little south of the present intersection of Benedict Hill Road, and the Town, after losing the lawsuit, was forced to reopen one and eight tenths miles of Cheese Spring Road, although it seems probably now that the Town officials did not follow the old highway precisely. (See also Benedict Hill Road and Mariomi Road.) (Source: New Canaan Historical Society)


    Cherry Street

    Running east and west between Park Street and Main Street, was opened up as a private project by two landowners wishing to sell building lots. In a land record dated February 23, 1826, it is referred to as "the cross road recently laid out," and it was accepted as a public highway by the Town at annual meeting of 1827. Consequently it may antedate Maple Street as the first cross street south of "Church Hill" between Park and Main Streets, since Maple Street was not begun until after November 1825. (Source: New Canaan Historical Society)


    Chichester Road

    Running northward from Wahackme to Greenley Road, resulted when an old driftway (possibly an abandoned road) was opened up in the early 1930's. In the nineteenth century, Wahackme Road was known as Chichester Road; in the mid-nineteenth century most Chichesters lived along present Greenley Road. (More research is needed to enlarge on the history of this road.) (Source: New Canaan Historical Society)


    Church Street

    Running east and west between Main Street, and South Avenue, was so named because the Methodist Episcopal Church was located on the northwest corner of the road at the Main Street end. Begun in 1904, work on Church Street was followed in a matter of weeks by the development of Oak Street and Green Avenue, the three streets being a project undertaken by the late Francis E. Green, realtor. Part of the area so developed had been known as Comsock Woods, a favorite picnic ground. (Source: New Canaan Historical Society)


    Clapboard Hill Road

    Only the highway winding downhill westward from Carter Street to Silvermine Road today preserves a piece of the name of "Ye Clapboard Hill Path to ye Meeting-house." (See under Carter Street.) (Source: New Canaan Historical Society)


    Colonial Court

    Dead-ending westward from South Avenue opposite the end of Church Street, was laid out and named in 1930 by Mr. Harold E. Mead. (Source: New Canaan Historical Society)


    Colonial Road

    Looping eastward from upper Valley Road and back to Valley Road farther north, was also laid out and named in 1930. (Source: New Canaan Historical Society)


    Comstock Hill Road

    Running westward from Silvermine Road and then turning south to run out of New Canaan into Norwalk, was the upper end of a very early highway that was laid out along the west side of Comstock Hill, leading to Huckleberry Path (Silvermine Road), and extending eastward to the mill near the present Silvermine Tavern. When Canaan Parish was formed in May 1731 a part of Comstock Hill Road was a piece of the Parish's southern boundary. For a time the road was labeled Buttery Road (which see), but New Canaan officially uses the Comstock Hill Road name now. (Source: New Canaan Historical Society)


    Conrad Road

    Running eastward from lower South Avenue and turning south to meet Gerdes Road, was developed in 1955. Conrad Road was the prize-winning name, submitted by Mrs. George Strathie of Park Street, in the developer's road-naming contest. The road runs through property of the late Conrad Moller, whose house faced Gerdes Road and whose sons operated an airport on the adjoining farmland -- hence the one-time name of Wild Blue Acres for this development. (Source: New Canaan Historical Society)


    Country Club Road

    Now running west from Smith Ridge to a dead end west of Oenoke Ridge, was laid out in 1731 as a connecting road from Smith Ridge to Canaan Ridge (upper Oenoke). At one time the steep hill west of Five Mile River was known as "Rat Tuttle's Hill," because Erastus Tuttle lived in the house near the road's steep bend. About the turn of the century, after the Country Club was organized, the section passing the clubhouse was considered a part of Lambert Road. The section west of Oenoke Avenue, formerly known as Blueberry Pond Lane, was hitched to Country Club Road in the late 1950's. (Source: New Canaan Historical Society)


    Cross Ridge Road

    Curving northwestward from North Wilton Road to Briscoe Road, was developed in the late 1950's to cross over Bartlett's Ridge. (Source: New Canaan Historical Society)


    Cross Street

    A private road dead-ending eastward from Baldwin Avenue, was planned to terminate at Summer Street, but the roadway has not yet been completed. (Source: New Canaan Historical Society)


    Crystal Street

    Dead-ending westward from South Avenue, and Grace Street (just to the south) were developed in 1926 by Aaron Weissmann of Stamford across what had been New Canaan's baseball park, complete with grandstand. With a deliberate change in spelling, Mr. Weissmann named Crystal Street for his father-in-law, Bernard Chrystal, New Canaan stationery store proprietor, and Grace Street for his secretary, Grace Kahn of Stamford. (Source: New Canaan Historical Society)


    Dabney Road

    Running east from Carter Street to Cedar Lane down old Silvermine Hill, was named for the daughter of Mr. Ernest Greene, one of the developers in 1952-56. (Source: New Canaan Historical Society)


    Danforth Drive

    Dead-ending northwestward from Bald Hill Road, was developed in the 1950's by Mr. and Mrs. Charles E. Danforth. (Source: New Canaan Historical Society)


    Dan's Highway

    Running easy and west between West Road and upper Ponus Street, is an eighteenth-century cross highway. Called Newman Street in the 1880's and then Dantown Road, it took the name of High Ridge Road (it does lead to High Ridge) about 1910 and the Lockwood Road (the pond is still known as Lockwood's Pond), which it retained until 1948 when the present form of the name was adopted. A number of Dan families were early homesteaders along the western end of the road. (Source: New Canaan Historical Society)


    Darien Road

    All that remains of the old highway is a short by-pass south of Exit 37 from the Merritt Parkway joining up with the extension of South Avenue. Originally Darien Road was the second of the "highways" laid out by Stamford by 1700 from the "country road" (present Post Road). It extended to the Perambulation Line, the dividing line between Norwalk and Stamford, which crossed the present Gerdes Road. Gerdes Road, although on the Norwalk side of the Line, was also called Darien Road; so was Brookside Avenue at a later time. The old Darien Road laid out by Stamford was cut off by the extension of South Avenue over the Merritt Parkway in 1938. (Source: New Canaan Historical Society)


    Davenport Ridge Road

    Only a short section of this old highway lies in New Canaan west of lower Ponus Street. Laid out in 1709, the road was run by Stamford surveyors from Newfield Avenue in Stamford to Ponus Ridge, taking its name from the land owned by the Rev. John Davenport, second pastor of Stamford. (Source: New Canaan Historical Society)


    Deer Park Road

    Dead-ending southward from Turner Hill Road, was developed in the 1930's through land that in the eighteenth century belonged to Moses Comstock, Sr., of Valley Road. It is named for the deer park that Mr. Comstock maintained somewhat to the east of the land through which Deer Park Roads was laid, the deer park being mentioned in William Cullen Bryant's "Letters of a Traveller." (Source: New Canaan Historical Society)


    Dogwood Lane

    Dead-ending southward from Wahackme Road into the old Kelly's Woods, was developed in 1936 and named for the dogwood trees that grew there. (Source: New Canaan Historical Society)


    Douglas Road

    Cut westward from South Avenue in 1945-46, absorbed Hope Avenue in 1954 to turn northward into Orchard Drive. When housing for veterans was nonexistent after World War II, a group of New Canaan citizens formed the Douglas Realty Co., which built the original section of Douglas Road and Gower Road was named for the Douglas firs along its route, the road crossing land formerly owned and cultivated by the Hoyt Nursery. (Source: New Canaan Historical Society)


    Down River Road

    Dead-ending eastward from lower Main Street below Lakeview Cemetery, was cut through between 1952 and 1955 to the bank of Five Mile River -- hence the name. (Source: New Canaan Historical Society)


    Driftway Lane

    Dead-ending off Spring Water Lane, was opened up during 1953-56 and first named Lesh Court. In 1959 the name was changed, on recommendation of the Historical Society and petition of its residents, to Driftway Lane, because from early days it had been a driftway to the upper mills or, more precisely, an extension of "driftway road," the old local name for present Spring Water Lane. (Source: New Canaan Historical Society)


    East Avenue

    Running eastward from New Norwalk Road at the Mill Pond to Main Street, was originally a part of the eighteenth-century Clapboard Hill Path to the Meetinghouse (see under Carter Street). Before New Norwalk Road was built, East Avenue extended to the intersection of Clapboard Hill and Silvermine roads. On the map of 1867 East Avenue is named Prospect Street. (Source: New Canaan Historical Society)


    East Cross Road

    Curving southwest from Hawks Hill Road into Hope Street in Springdale, follows the course of a old highway that began on the hill near Jelliff Mill and ran across Hope Street to Newfield Avenue. The original road was cut in two by the Merritt Parkway, but the north end was never officially closed, causing a legal contest in the late 1930's. (Source: New Canaan Historical Society)


    East Maple Street

    Running from Main to Hoyt Street as an extension of Maple Street, was surveyed in 1904 from Stephen B. Hoyt, Sr., as the second of the three roads put through the old fifty-acre Hoyt farm that was near the center of town. (Source: New Canaan Historical Society)


    Echo Hill Road

    Dead-ending west from Silvermine Road north of the Silvermine Guild, is a private road, named by its residents for their unique hillside. (Source: New Canaan Historical Society)


    Elm Place

    Winding eastward from Woodland Road to Main Street, and Woodland Road were parts of a development called The Woodlands that was laid out in 1912. After one house was built on Woodland Road, little else was done until the 1930's. (Source: New Canaan Historical Society)


    Elm Street

    Running east and west between Main Street and Weed Street, began its life in the winter of 1848-49 when a highway was laid eastward from Park Street to Main Street. In 1858 it was extended westward from Park Street to the intersection to Seminary Street, and in 1868 it was renamed Railroad Avenue. Not until 1935 was the earlier name of Elm Street restored. According to story, Elm Street was first named by William E. Dann, who came here in 1851 from Stamford and acquired a grocery story and a livery stable on the south side of the block from Main Street to South Avenue. Wishing to impress his two clienteles, Mr. Dann went to New York to order announcement cards and coined Elm Street when the printer insisted his business should have street addresses. (Source: New Canaan Historical Society)


    Evergreen Road

    Looping northeastward from Benedict Hill Road to Cheese Spring Road, was opened in 1958 and named for trees in the neighborhood. (Source: New Canaan Historical Society)


    Fable Farm Road

    Dead-ending northward from Silvermine Road a little west of Valley Road intersection, was built in 1959. When novelist Faith Baldwin bought part of the farm that had been in the St. John family for some two hundred years, she called the place "Fable Farm," because she liked to think of her stories as "fables." Cut in east of the old St. John barn, the road was given Miss Baldwin's name for the farm. (Source: New Canaan Historical Society)


    Fairty Drive

    Running westward from South Avenue opposite Hawthorne Road to meet Park Place, was in1848 cut through a piece of the old Farity orchard that extended from Old Stamford Road to South Avenue. (Source: New Canaan Historical Society)


    Farm Road

    Running east and west between South Avenue (at north end of the High School) to the junction of Main Street, White Oak Shade Road, and Old Norwalk Road, was opened in the mid 1950's. The entire development, known as Village Farm, comprises thirty-seven acres of the old farm owned by the Misses Weed (who lived on White Oak Shade Road) into which Farm Road, Field Crest Road, Tommy's Lane, and Village Drive were cut. (Source: New Canaan Historical Society)


    Father Peter's Lane

    A private road dead-ending southward near the eastern end of Michigan Road was built in 1936 and was named for the first Peter Smith, grandson of Samuel Smith who was granted land on "Smith's Ridge" by Norwalk about 1700. Some people contend that the road name should have been "Uncle Peter's Lane," because "Uncle" Peter Smith, who died in 1875m was the fourth Peter Smith and the last Smith landowner of the property. (Source: New Canaan Historical Society)


    Fawn Lane

    Dead-ending southeast off Thayer Pond Road, was built in the late 1950's and named because the woods through which it was cut could have been a deer cover. The road, actually, is not far east of the old Comstock deer park (see under Deer Park Road). (Source: New Canaan Historical Society)


    Ferris Hill Road

    Running west from Valley Road to Canoe Hill Road up the hill once known as Upper Canoe Hill, is an eighteenth-century highway named for Deacon Darius Ferris, son-in-law of Abijah Comstock (son of Moses Comstock, 2d), who owned much of the neighborhood land and the mill on Five Mile River. The name Ferris Hill was used in the nineteenth century, although the highway once was better known as "Pock House Hill," because the foundations of an early smallpox isolation house were visible until about 1900. (Source: New Canaan Historical Society)


    Field Crest Drive

    Looping northward from Farm Road and back again, was built in 1956-58 and named for its location. (See under Farm Road.) (Source: New Canaan Historical Society)


    Forest Street

    Running northward from East Avenue at Sillman's store to the junction of Parade Hill Road and New Norwalk Road, was begun in 1858 when the town laid out one block northward from the old tanyard of Frederick Ayres on the north side of Clapboard Hill Road (East Avenue) to the dooryard of George Armstrong on the west side of Locust Avenue (then called Brushy Ridge Road). By 1867 it had been extended northward and seems to have been called North Street, which was once the name of Greenley Road. On the map of 1878 it is labeled Forest Street. (Source: New Canaan Historical Society)


    Fox Run Road

    Dead-ending westward from Mariomi Road, was developed and named in 1954-56. (Source: New Canaan Historical Society)


    Frogtown Road

    Winding northeastward from Ponus Street to Weed Street, was laid out in 1734. By 1770 there were four houses on the road, three owned by Weed families. By 1900 only one house remained, that of "Billy" Jones, whom Will Kirk, editor of the New Canaan Messenger, christened "the mayor of Frogtown." The name seems to have stuck, replacing the name of Jones Street listed in the 1888 Directory. An early landmark on the road was the "old stone fort" built near the brook by Stephen Weed after he was released, with mind deranged, from the Sugar House Prison in New York City where he had been imprisoned as a Revolutionary soldier. (Source: New Canaan Historical Society)


    Garibaldi Lane

    Winding northwestward from the sharp corner of Brushy Ridge Road to Smith Ridge Road, is a part of an old seventeenth-century highway that continued farther north. (See Brushy Ridge Road.) By mid-nineteenth century only the section from Brushy Ridge to Strawberry Hill was open. Later in the nineteenth century when the Brushy Ridge hillcrest was called Mount Lebanon (see also under Brushy Ridge Road), the highway was called Lebanon Avenue. Sometime after 1910 it became Garibaldi Street (later Lane), because from 1902 (when he came to New Canaan) until 1914, the late John Garibaldi occupied the only house then standing on the road. (Source: New Canaan Historical Society)


    Gerdes Road

    Running east and west between South Avenue and White Oak Shade Road, just north of the Merritt Parkway, was originally Norwalk's section of Darien Road (which see). About 1948 the present name was given the highway by the Southern New England Telephone Company, when the late Mr. and Mrs. Augustus M. Gerdes were the only residents on the south side of the road. (Source: New Canaan Historical Society)


    Gerrish Lane

    Dead-ending westward from Oenoke Ridge about opposite the new St. Mark's Church, in the early 1930's was cut through land of "Uncle" John Gerrish, former summer resident from Brooklyn, whose front lawn facing Oenoke was always available for small-fry baseball games after his large residence had burned to the ground about 1905. (Source: New Canaan Historical Society)


    Gower Road

    Run westward from South Avenue in 1945-46, was extended to Old Stamford Road in 1951 (see under Douglas Road). It uses the maiden name of Mrs. Northrop Dawson of Oenoke Ridge. (Source: New Canaan Historical Society)


    Grace Street

    Dead-ending westward from South Avenue almost opposite Farm Road, was laid out simultaneously with Crystal Street (which see). (Source: New Canaan Historical Society)


    Gravel Island Road

    A private loop to the west off Valley Road and back again not far from Turner Hill, was named in the 1930's by its residents, who struck, literally, a gravel hill when they began excavations. (Source: New Canaan Historical Society)


    Green Avenue

    Running north and south between Church and Oak streets, was a part of a development made in 1904 by the late Francis E. Green (see Church Street). When the street signs mysteriously acquired an extra "e" and became Green Avenue in the 1930's, the late Hanford S. Weed stormed the Town Hall to make certain the signs were corrected and his friend's name accurately perpetuated. (Source: New Canaan Historical Society)


    Green Meadow Lane

    Dead-ending eastward from White Oak Shade Road to the bank of Five Mile River, was built in the early 1950's as Oswin Lane, taking its present name in 1957 from the meadow of the old Charlie Fish farm. (Source: New Canaan Historical Society)


    Greenley Road

    Running east and west between Ponus Street and West Road, was laid out by the Stamford proprietors in 1709 and continued up West Road (which see). In early days it was known as the "Road over Hoyt's Ridge (or Brushy Ridge)." Later, when West Road was known as West Street, Greenley Road was called North Street. Although it runs through land originally owned by Hoyts, Chichesters, and Fanchers, the highway takes its present name from mid-nineteenth century residents who spelled their surname "Greenly." The road appears on maps and in deeds as Greenly Avenue or Greenly Road until the 1920's when the third "e" somehow was acquired. The old Greenley farm was long known as "Indian Cave Farm," because artifacts founds in a cave on the property seemed to indicate that the cave once had been used as a shelter by Indians. (Source: New Canaan Historical Society)


    Grove Street

    Running north and south between Richmond Hill Road and Elm Street, was laid out by the Town in 1873 to cross the new railroad tracks just east of the roundhouse. It was probably named for the grove of the trees, mentioned in old records, that stood south of Seminary Street until Elm Street was extended westward from Park Street in 1858. (Source: New Canaan Historical Society)


    Guild Drive

    A private road dead-ending southward into Norwalk from Comstock Hill Road, was opened in 1955-56 and named for near-by Silvermine Guild. (Source: New Canaan Historical Society)


    Hampton Lane

    A private road now dead-ending eastward from Oenoke Ridge, was begun in the early 1950's and planned to connect later with Parade Hill Road. It is named for the near-by inn. (Source: New Canaan Historical Society)


    Hanford Lane

    Dead-ending south through former Weed property midway across Frogtown Road, was developed in the mid 1950's and named by the late Llewellyn Ross, former town Democratic chairman, to honor the late Hanford S. Weed, another former Democratic chairman, state senator, lawyer, and well-known descendant of early settlers. (Source: New Canaan Historical Society)


    Harrison Avenue

    Running east and west between South Avenue and Main Street (opposite entrance to Lakeview Cemetery), was laid out as a real estate development in 1892 and named for Benjamin Harrison, President of the United States in 1888-92, at the time Harrison was defeated for re-election by Grover Cleveland. (Source: New Canaan Historical Society)


    Hawks Hill Road

    Running eastward from lower Ponus Street, was laid out in 1950 as Cross Road. Spurning the name of Heckett's Hill, which was used by the Stamford proprietors and in early land records, the road took the surname of Henry and Flora A. Hawks who, beginning in 1902, bought considerable acreage in the vicinity. (Source: New Canaan Historical Society)


    Hawthorne Road

    Running eastward from South Avenue to Elm Place, was added to the plans for The Woodlands (see Elm Place) after 1915 but not laid out or named until much later. (Source: New Canaan Historical Society)


    Heather Drive

    Being cut eastward from Cedar Drive in 1960, was named by the developer. (Source: New Canaan Historical Society)


    Hemlock Hill Road

    Looping southward from Oenoke Ridge to West Road just west of the end of Weed Street, was developed in the mid 1950's and was named for the trees in the vicinity. (Source: New Canaan Historical Society)


    Hickok Road

    Running eastward from Valley Road to Mariomi Road, was developed about 1954 by the late Clarence E. Costales through land that had belonged to his great-grandfather Hickok whose home stood on Valley Road.


    Hickory Lane

    Dead-ending northward from Carter Street, was developed in 1947-49 as Hickory Drive. The name comes from trees in the neighborhood. (Source: New Canaan Historical Society)


    Hidden Meadow Lane

    A private road dead-ending northeastward from Laurel Road (No. 1), was begun about 1949 by the late Clarence E. Costales as Hickory Ridge and known during 1949-51 as Hickok Lane, both names being changed to avoid confusion with existing road names. North of Mr. Costales' late residence is the "hidden meadow" -- hidden from view from both Laurel and Valley roads -- whereto residents of the neighborhood rushed their bows and valuables when word came to them that the British, after the burning of Danbury and the battle of Ridgefield, were raiding westward from the road to Norwalk. A reliable account states that marauding parties actually reached near-by Bald Hill. (Source: New Canaan Historical Society)


    Highview Terrace

    Dead-ending westward from Old Stamford Road north of the juncture with Lapham Road, was built in 1954-55 and named for its site. (Source: New Canaan Historical Society)


    Hillcrest Road

    A loop from Spring Water Lane to the west and back again, was built in 1952-54. Actually the "crest" of the hill is Ponus Ridge. (Source: New Canaan Historical Society)


    Hillside Avenue

    Road signs to the contrary, winds from the corner where Locust Avenue become Brushy Ridge to Ledge Avenue (see under Brook Street). (Source: New Canaan Historical Society)


    Hillside Road

    Running southeast from Forest Street to Locust Avenue was built about 1908 over a rocky hillside. (Source: New Canaan Historical Society)


    Hollywood Avenue

    Dead-ending northward from Old Norwalk Road just east of Five Mile River, was build about 1955. (Source: New Canaan Historical Society)


    Holmewood Lane

    Dead-ending eastward from Oenoke Ridge at the Holmewood Inn, was built in 1933 and is New Canaan's narrowest public road with only a twelve-foot right of way. (Source: New Canaan Historical Society)


    Horton Lane

    Dead-ending west from White Oak Shade Road near Nursery Road, was opened in 1959 through property owned by the Horton family, who came to New Canaan in the late nineteenth century. (Source: New Canaan Historical Society)


    Hoyt Street

    Running northeastward from Main Street to East Avenue was laid out in 1890 by the late Stephen B. Hoyt, Sr., as the first of several proposed roads through the fifty-acre Hoyt farm near the center of town. East Maple Street and Raymond Street, however, were the only other roads developed. (Source: New Canaan Historical Society)


    Huckleberry Hill Road

    Running eastward from Valley Road into Wilton, was laid out about 1735 as a crossroad leading to the Comstock Mill on Silvermine River (on the present Flyod C. Noble property). The Wilton end of the road probably antedates the New Canaan section, connecting with the important Huckleberry Hill roads in Wilton (see map of Wilton). (Source: New Canaan Historical Society)


    Husted Lane

    Dead-ending northward from the intersection of Main Street and Locust Avenue, developed from a seventeenth-century driftway. Shown as Husted Avenue on the 1967 map, it was called Husted Place in the 1888 and 1915 Directories, and only later became Husted Lane. It is named for a prominent eighteenth-and nineteenth-century family who owned much land in the center of town. Research on this road would be interesting and historically valuable. (Source: New Canaan Historical Society)


    Indian Rock Road

    Dead-ending northward from Country Club Road opposite Lambert Road, was opened up in 1948. The road passes a little westward of the Indian Rocks (not rock), not far from Five Mile River, where Indian Rock Road probably follows in part a very old road leading to the mill near the present New Canaan Reservoir. (Source: New Canaan Historical Society)


    Indian Waters Drive

    Dead-ending westward from Weed Street below "Ye Clefts" and near the place where the east branch of Noroton River crosses Weed Street, was opened in the mid-1950's. (Source: New Canaan Historical Society)


    Inwood Road

    Dead-ending southward into Norwalk from Silver Ridge Road, was run into the woods in 1956-58. (Source: New Canaan Historical Society)


    Jelliff Mill Road

    Running east and west between Ponus Street and the lower end of Old Stamford Road just north of the Merritt Parkway, was laid out in two sections. The eastern end was laid out by Stamford surveyors to the mill before 1730; the western end was laid out by the Town of New Canaan "from Alfred Hoyt's dooryard" on Ponus Street eastward in 1866. The present road name uses the surname of the family which has operated the mill since 1869. The original mill was built before 1720. (Source: New Canaan Historical Society)


    Jennifer Lane

    Dead-ending northward from Michigan Road was developed in 1953-55 into former Keeler property and named for a granddaughter of John E. Warner, Sr. (Source: New Canaan Historical Society)


    John Marshall Place

    A private dead-end spur off Father Peter's Lane, was built in 1954 and named by its residents. (Source: New Canaan Historical Society)


    Jonathan Road

    Dead-ending eastward from Barnegat Road toward a region known as Plesant Ridge, was built in 1956-59 and named for a grandson of John H. Brotherhood, one of the new developers. (Source: New Canaan Historical Society)


    Journey's End Road

    Now dead-ending eastward from Bald Hill Road at the northeast corner of New Canaan, should have been called instead the "Lost Highway." Deeds to several parcels of property in this vicinity referred to "a highway" as a boundary but no trace of a road that may once have connected with the "east road" in Vista or extended into Wilton could be found. Consequently, the Town had to "restore" the highway in 1940. (Source: New Canaan Historical Society)


    Juniper Road

    Was cut eastward from Hickory Lane in 1948 through Hoyt Nursery property and in 1955 extended to Cedar Road on old Silvermine Hill. It takes its name from the evergreen tree family. (Source: New Canaan Historical Society)


    Kelly Green

    (not Kelly's Green), dead-ending eastward from Woodland Road near South Avenue, was opened up in 1951-52 and named for its developer, James J. Kelley. (Source: New Canaan Historical Society)


    Kimberly Place

    Dead-ending northward from Elm Street west of Seminary Street, was completed in 1939. Although it lies almost along the old Perambulation Line (along which lies the stone wall back of houses on the west side), the street was named for Mrs. Emma F. Kimberly, who until 1928 lived in the house built by her father and mother, Charles and Clarissa Slosson Darrah, in 1852. The house stood on Elm Street about where Kimberly Place begins. (Source: New Canaan Historical Society)


    Knapp Lane

    Dead-ending westward from Weed Street south of Indian Waters Drive, was developed in 1955-57. (Source: New Canaan Historical Society)


    Knollwood Lane

    Dead-ending westward from Mariomi Road, was built in 1956-58 and named for its site. (Source: New Canaan Historical Society)


    Lakeview Avenue

    Running eastward from Main Street across Five Mile River along the north end of Lakeview Cemetery, becomes Town Road and so now ends at New Norwalk Road. The western end of the road is the old eighteenth-century "Hanford's path to the mill" (the mill stood on Five Mile River) but was laid out again by the Town in 1827-29. Lakeview Avenue appears on mid-nineteenth-century maps as Cemetery Avenue ad then as Cemetery Street, the name it kept until 1914 or later when the lake in the cemetery gave both the cemetery and the road their names. The first bridge was built and the road extended to the Cemetery in 1869 when a piece of Marvin Ridge Road was abandoned. The connection to New Norwalk Road has just been made. (Source: New Canaan Historical Society)


    Lake Wind Road

    Looping eastward from upper Ponus Street and back again, was developed in 1956-58. (Source: New Canaan Historical Society)


    Lambert Road

    Running northeast from Oenoke Ridge to Country Club Road, is an early highway, probably laid out as a short-cut for the concenience of travelers from two directions: those coming from Stamford up the old "Ridgefield Road" (Weed Street) across West Road on their was to Smith Ridge and on to Ridgefield; and those coming up the old Haynes Ridge (now lower section of Oenoke Ridge) on their way to Smith Ridge. The junction known in early days as Elm Corner, with its blacksmith shop, was an important stopping place for man and beast. Named Gold Road after the New Canaan Golf Club (Country Club) came into existence in 1899, the road was renamed Lambert Avenue in 1908 in honor of Dr. Edward W. Lambert, chief instigator and first president of the Country Club. Later it was called Lambert Ridge Road, taking its present form in 1948. The hill where the present Anderson house stands was once called Bright Knoll (when the Brights were owners) and also Honeysuckle Hill. (Source: New Canaan Historical Society)


    Lantern Ridge Road

    Dead-ending north from North Wilton Road eastward of Valley Road, was opened in 1956 and named by Charles F. Morton, its original developer for "no special reason." (Source: New Canaan Historical Society)


    Lapham Road

    Running northward fro New Canaan-Darien line at the Talmadge Hill Chapel to merge into Old Stamford Road, is a constitution of the present Hollow Tree Ridge Road in Darien. The original road was one of a "country road" (present Post Road). It ran over Great Ox Ridge and extended up present Old Stamford Road to the Perambulation Line at the corner of the present Bank Street and Park Street. The highway sometimes was called "the Path that goeth to meet the Perambulation Line." Sometimes called the "old road" after South Avenue was built or Christy's Road because it led to the Christy Hill in Glenbrook, it became Lapham Avenue in 1909, because the late Lewis H. Lapham owned all the lands on either side. It 1952 its name became Lapham Road. (Source: New Canaan Historical Society)


    Laurel Road

    New Canaan has two Laurel Roads. No. 1, winding northward from Canoe Hill Road to North Wilton Road, is an early eighteenth-century highway that may have been called Kellogg's Ridge Road. In the nineteenth century it was known as Farm Road, Poorhouse Road, and Town Farm Road after New Canaan's Poor Farm was located about midway from either end of the road. About 1930 it took the name of Laurel Road for Connecticut's state flower that grows in profusion along its route. Until the 1930's only one house had ever been built north of the location of the Poor Farm: the cottage that Miss Diana Richards built for her Negro slave Grace when she married Ben Smith about 1825. After the Smiths died, the house was unoccupied and fell into ruins. The north end of the road nearly followed suit and was almost impassable. Laurel Road No. 2, running west from upper Ponus Street to High Ridge Road in Stamford, was developed in 1956. It takes its name from Stamford's Laurel Reservoir, which submerged several old roads. (Source: New Canaan Historical Society)


    Ledge Avenue

    A connecting road eastward from New Norwalk Road to Urban Street, was a part of Brookside development (see under Brook Street). (Source: New Canaan Historical Society)


    Leslie Lane

    A private road running southwest from Whitney Place to Park Street, was opened up in the late 1940's by the sisters of Postmaster Frank Leslie. (Source: New Canaan Historical Society)


    Leslie Road

    Dead-ending southward from Michigan Road, is a private road opened about 1959. (Source: New Canaan Historical Society)


    Llewellyn Drive

    Dead-ending north and westward from Frogtown Road, was built in 1957 and named for the late Llewellyn Ross, who planned its development. (Source: New Canaan Historical Society)


    Lockwood Avenue

    Running south from Bank Street to Mortimer Street, was one of the three roads laid out in 1915 as part of Prospect Heights (see under Brinckerhoff Avenue). (Source: New Canaan Historical Society)


    Locust Avenue

    Running east and west from Main Street at the firehouse across New Norwalk Road to the foot of Brushy Ridge Road hill, originally was a part of the eighteenth-century highway known from 1732 as the "Brushy Ridge Path to the meeting-house." This was one of the five roads that were like spokes of a wheel of which the hub was the first meeting-house. Locust Avenue appears o the 1867 map as River Street but is called Locust Avenue on the map of 1878. Yet in 1878 the New Canaan Messenger, congratulating residents for planting maple trees on either side of the road, announced that henceforth it would be called Maple Street -- probably a bit of Editor Will Kirk's humor because New Canaan already had its Maple Street. (Source: New Canaan Historical Society)


    Logan Road

    Swinging northwest from upper Oenoke Ridge to Pinney Road, was opened up in 1955-57 and named for a grandchild of John H. Brotherhood, one of the developers. (Source: New Canaan Historical Society)


    Lone Tree Farms Road

    Dead-ending southward from Brushy Ridge Road was laid out in 1952 and in 1958 absorbed Lone Tree Lane, a branch to the east. The road passes the Lone Tree (sugar maple) that was one of the best known early landmarks, near the house of Caleb Benedict, one of the founders of the Canaan Parish. (Source: New Canaan Historical Society)


    Louise's Lane

    Dead-ending southward from Pinney Road east of West Road, was laid out in 1950 and named for the late Louise Warren Higley. (Source: New Canaan Historical Society)


    Ludlowe Road

    Dead-ending westward from Canoe Hill Road, was opened up in 1955-57. A near-by resident suggested to the Norwalk developer that the road be named for Roger Ludlow, who in 1640 purchased from the Indians the land between Norwalk and Saugatuck rivers, now occupied by East Norwalk and a part of Westport. The deed of purchase in the Norwalk records is a copy of the original by a town clerk who misspelled Ludlow. The correct spelling is without the final "e"--Ludlow. (Source: New Canaan Historical Society)


    Lukes Wood Road

    Curving northeastward from the intersection of Oenoke Ridge and Pinney Road to Puddin' Hill Road in New York State, is part of an eighteenth-century highway that was an important connecting road for travelers going to and from upper Smith Ridge and Pound Ridge. The name is a corruption of Luke's Woods through which the road runs. For a number of years Oenoke Avenue, as Oenoke Ridge was then called, extended to Michigan Road, but in 1948 the Town arbitrarily terminated Oenoke Ridge at Pinney's Corner and included the section of the road from the corner to Michigan Road in Lukes Wood Road. (Source: New Canaan Historical Society)


    Main Street

    Today running northwestward from the juncture of White Oak Shade Road with Old Norwalk Road to the end of Oenoke (Haynes) Ridge at old St. Mark's Church on God's Acre, was laid out about 1722 as the upper end of a important highway leading past the many miles along Five Mile River and extending along the eastern side of White Oak Shade Ridge. (See White Oak Shade Road.) After the meeting-house site had been established by the committee of the General Assembly on October 26, 1731, about twenty roads west of "Canaan Road," Canaan Road or White Oak Shade Road or present Main Street, however you wish to consider it, was one of the five roads that, like spokes of a wheel, led to the meeting-house hub. From then on the highway was referred to as Canaan Road until the various small shops appeared after 1800 to give it the prosaic name Main Street. In the past decade the Town has eliminated the designations of North Main Street and South Main Street and calls all the street Main Street. (Source: New Canaan Historical Society)


    Maple Street

    Running east and west between Park Street and Main Street, was the first cross road below "Church Hill" (but see Cherry Street). The Town voted on November 10, 1825, to lay out the road which probably put through almost immediately because it was accepted by the town meeting of October 1826. The East Maple Street extension was surveyed in 1904. (Source: New Canaan Historical Society)


    Mariomi Road

    Winding northeast from Valley Road to connect with Cheese Spring Road southwest of Benedict Hill, was laid out about 1940 and did not precisely follow the route of an old (1879) road (see Cheese Spring Road). Its name is a corruption of Mary Naomi -- Mary Naomi St. John. Miss St. John in the nineteenth century lived on the west side of Valley Road, but also owned land on the east side near the old swimming hole in Silvermine River where small boys dedicated to shock her by swimming in the nude. Precisely where Mariomi ends and Cheese Spring begins is a matter of dispute (the Town simply assigned house numbers consecutively and doesn't care which name a resident picks), and efforts to rename the entire road Cheese Spring have not been successful. If ever the road is renamed, it should be Cheese Spring Ridge Road. (Source: New Canaan Historical Society)


    Marshall Ridge Road

    Curving northeastward from Weed Street to Richmond Hill Road, was a development laid out in 1897 through the old Marshall Farm. The Weed Street end was probably and old driftway. James R. Marshall, a descendant of a Greenwich family, bought a large part of the old farm of Deacon Samuel Bouton in 1868. He lost it by foreclosure eight years later, but his name clung to the land -- hence Marshall Ridge Road. (Source: New Canaan Historical Society)


    Marvin Ridge Road

    Running southward from Old Norwalk Road to become Weed Avenue in Norwalk south of the Merritt Parkway, was in existence by 1720 as a way over "Marvin's Hog Ridge," a name indicating that David Marvin had been given permission to pasture his swine there before the area was divided into individual grants. (A colony law prohibited swine to run loose within three miles of a town.) The ridge extended from the Middle Clapboard Hill along the east side of the Five Mile River and sloped down west of the south end of the east side of the Five Mile River and sloped down west of the south end of Brushy Ridge. The original road extended north of the present Old Norwalk Road up to the Mill Pond and the Clapboard Hill Path at the point where New Norwalk Road now crosses East Avenue. After Lakeview Cemetery was established, the Town voted in October 1869 to abandon that section of Marvin Ridge Road from the northeast corner of the cemetery to the "Norwalk-New Canaan" Road (present Old Norwalk Road). It is probable that the short stretch from the mills to East Avenue was lost in the widening of Five Mile River into the Mill Pond. In the late nineteenth century, Marvin Ridge Road was called Old Norwalk Road, assuming its present name by 1909. (Source: New Canaan Historical Society)


    Mead Street

    Running east and west between Park Street and South Avenue, was opened up in 1890 by the late Benjamin P. Mead an influential citizen whose family later gave Mead Memorial Park to New Canaan. (Source: New Canaan Historical Society)


    Meadow Lane

    A block-long connection between Woodland and Hawthorne roads, was laid out in the 1930's when the Woodlands development got under way. (See Elm Place.) (Source: New Canaan Historical Society)


    Merritt Parkway

    Crossing the southern end of New Canaan, is the only road running east and west that is a state highway. Projected in 1925, the section through New Canaan was not completed until 1938. The parkway is named for the late Schuyler Merritt, U.S. Congressman from this district. (Source: New Canaan Historical Society)


    Michigan Road

    Now running westward from Smith Ridge Road to join Lukes Wood Road, is a seventeenth-century crossroad that probably was laid out at more than one time. Some time after the eastern end was laid out in 1731, one branch of the highway ran southward to Lockwood's Mill, near the present Reservoir dam, and then westward to Oenoke Ridge. When the reservoir dam was raised, a portion of this part of Michigan Road went under water and the maps also show the road continuing along its present western route. There are so many versions of the story of the crotchety resident of the road who was always going to go home to "Michigan" that this explanation of the road name seems apocryphal. More research might reveal a better reason. (Source: New Canaan Historical Society)


    Mill Court

    Dead-ending west from Millport Avenue near the site of the old mills, was built in 1950. (Source: New Canaan Historical Society)


    Mill Road

    Running northward from the Norwalk line along Silvermine River to turn westward into Silvermine Road, is an early eighteenth-century road leading to old mills, now demolished. Until 1948 the connecting link to Silvermine Road from the river at the north end of Mill Road was called South Wilton Road. (Source: New Canaan Historical Society)


    Millport Avenue

    Following along the west bank of Five Mile River northward from the entrance to Lakeview Cemetery on Main Street to East Avenue, is an early eighteenth-century path that once led to the two mills -- grist and saw -- that stood near the foot of the present Lakeview Avenue. In the nineteenth century the highway was called Mill Street, and for a time the entire region was called Millport. (Source: New Canaan Historical Society)


    Mink Lane

    Dead-ending westward from Cheese Spring Road, was build in 1959. (Source: New Canaan Historical Society)


    Morse Court

    The northern access to the town parking lot from either Main Street and South Avenue, is not considered by the Town to be a separate road. This leaves the stores and offices facing the parking lot without an address. The name comes from the Morse family which owned the Birdsall House, the Main Street hotel that was demolished to make way for the parking lot. (Source: New Canaan Historical Society)


    Mortimer Street

    Running westward from South Avenue to Brinckerhoff Avenue, south of Bank Street, was laid out as a part of Prospect Heights. (See Brinckerhoff Avenue.) (Source: New Canaan Historical Society)


    Myanos Road

    Opened in 1952 northward from Wahackme Road to Toquam Road (which see) and extended in 1954 westward to a dead end, honors an Indian chieftain who was overlord of the region west of the Myanos River but had no holdings in this area. Note to Future Namers of Highways in This Vicinity: An appropriate Indian name is that of Penahay, known grandson of Ponus and the last one to be so designated in Stamford deeds. (Source: New Canaan Historical Society)


    New Norwalk Road

    Better known as Route 123, is a north-south state highway running from the Norwalk line at the southern end of Carter Street to join Smith Ridge Road at Parade Hill Road. It was laid out and put through between 1931 and 1935 as a more direct road than Old Norwalk Road, the eastern end of which was incorporated into the new road after considerable straightening. (Source: New Canaan Historical Society)


    Norholt Drive

    Dead-ending westward from Smith Ridge Road south of Country Club Road, was opened up in 1953. Its name is a contraction of the surnames of the developers, George Norrick and Harold Holt. (Source: New Canaan Historical Society)


    North Wilton Road

    Running eastward from Smith Ridge Road into Wilton, was in existence when Canaan Parish was established, being a convenient way from the meeting-house in the Parish of Wilton (founded 1727) to the old Oblong. It was along this road that farmers along the Silvermine River feared the British would come foraging on their return from Ridgefield to Norwalk. It is said that a party actually was detached from the army and sent down Ridgefield Road (Route 33), over the Vista Road, to the Lockwood Farm in the Oblong to collect cattle. They may well have done some foraging around and over Bald Hill as a reliable story insists they did. Until the 1930's, the eastern end of North Wilton Road was known as DeForest Road, which name Wilton retains, using the surname of a family resident in the area from before the Revolution. South Wilton Road was present Mill Road. (Source: New Canaan Historical Society)


    Nubel Lane

    Dead-ending eastward from Marvin Ridge Road, was given the surname of one of the men who developed it in 1954-57. (Source: New Canaan Historical Society)


    Nursery Road

    Running eastward from White Oak Shade to the Norwalk town line, was ordered laid out by the Proprietors of Norwalk in 1722 below the great Hanford's Swamp. As it formed part of the southern boundary of Canaan Parish when the Parish was established in May 1731, it was often mentioned in early grants and deeds as the dividing line. Known as Lynes Road before 1900, it was renamed Nursery Road many years ago because it crossed the old Comstock Nursery in Norwalk and skirted a portion of the Hoyt Nursery in New Canaan. When the Merritt Parkway was built in 1938, Nursery Road was cut in two. (Source: New Canaan Historical Society)


    Nutmeg Lane

    Dead-ending northwestward from lower Brushy Ridge Road, is a private road built about 1955 and named, presumably, for the nickname of Connecticut -- the Nutmeg State. (Source: New Canaan Historical Society)


    Oak Grove Place

    Dead-ending southward from Old Stamford Road about opposite the entrance to the Bird Sanctuary, is a private road that grew out of a "cowpath" into property opened up by Harry and Percy Offen. It was named about 1952 for the oak grove that is still standing. (Source: New Canaan Historical Society)


    Oak Street

    Running east an west between South Avenue and Main Street, as begun in 1904 (see under Church Street). Part of the oak woods (also known for a time as Comstock Woods) still stands on the south side of the road. (Source: New Canaan Historical Society)


    Oenoke Glen

    A private dead-end development eastward from Oenoke Ridge about opposite Hemlock Hill Road, was opened up in the late 1950's. (Source: New Canaan Historical Society)


    Oenoke Lane

    Opened in the 1930's to a dead end westward from Oenoke Ridge about opposite the Historical Society's house, was curved southward in 1958 to terminate near the intersection of Prospect Place and St. John Place. (Source: New Canaan Historical Society)


    Oenoke Ridge

    Curving northward from the end of Main Street at old St. Mark's Church on God's Acre to the junction of Pinney and Lukes Wood roads, was "bounded off" by the Proprietors of Norwalk in 1711 when owners of land along the upper section "in a place called Canaan" petitioned for a highway to give them access to their property. The upper section of the road ran along the easy side of what was called Canaan Ridge. The lower section ran along Haynes Ridge, which took its name from Mr. William Haynes to whom Norwalk Proprietors had granted ninety-three acres of land on the ridge below Elm Corner (Lambert Road juncture) in 1705. Unfortunately, some time after 1875 the name Oenoke crept into use. Canaan Ridge and Haynes Ridge were forgotten, and the road became Oenoke Avenue. In 1942 Oenoke Avenue was officially renamed Oenoke Ridge. Oenoke (also called Owenoke, Onox, Onocks, etc.) was a son of Ponus, but was absent from Stamford after his father sold his lands to the agent of the New Haven Colony in 1640. The land deeded by Ponus gave no bounds, but when the grant was confirmed by Katonah, who had assumed leadership of the remnants of several Indian tribes, the land extended to Five Mile River and northward into Vista. Until the final bounds of the old Oblong and the Eight Mile (New York) Line were set in 1731, Stamford claimed this land to Five Mile River and into present Westchester County, thereby claiming both Haynes and Canaan ridges. However, Oenoke's connection with New Canaan is farfetched. (Source: New Canaan Historical Society)


    Ogden Road

    Running north from Lukes Wood Road to Bowery Road at Mud Pond, was laid out by the town in 1866 and cut through in 1869 to provide easier access to Ogden's mill when the older road to the west, present Wakeman Road, proved too steep for wagons in bad weather. (Source: New Canaan Historical Society)


    Old Kings Highway

    New Canaan has two roads so named No. 1, running northward from Old Norwalk Road to loop into New Norwalk Road, was built about 1945 and for a short distance at its southern end parallels the section of Marvin Ridge Road that the Town abandoned in 1869. No. 2, dead-ending south from Country Club Road almost opposite the Country Club's tennis courts, combines a twentieth-century stretch and a reopened fraction of an abandoned road. About 1903 Adrian Van Sinderen received permission to close off the upper end of an abandoned road that crossed his property (now the Swan place) and terminated on Lambert Road about where the Swan's driveway is, provided he would make a new northern terminus to the road. This highway, which appears as an abandoned road on the 1867 map, was once called Nigger Lane, because its only resident was Uncle Ned, a slave whom Samuel Smith had freed in 1825. Originally the road was a continuation of present Garibaldi Lane (which see) long before the lower section of Smith Ridge was laid out in 1858. Use of the name Old King's Highway for either road appears now to be romantic license. Under orders from King James II, the Connecticut Colonial Court passed a law that all highways between plantations (settlements) were to be known as "country roads" or King's highways, and in 1709, under orders from Queen Anne, these roads were brought under control of the Crown. "Country roads" hence were the early designations for "post roads." Since neither of New Canaan's Old King's Highways ran from Norwalk's post office, neither was likely to have been a post road. An abandoned road off Laurel Road (No. 1) and present Pinney Road may well have been parts of a post road from Wilton to Pound Ridge and Bedford. The entire matter is an interesting research project for anyone willing to undertake it. (Source: New Canaan Historical Society)


    Old Norwalk Road

    Running westward from New Norwalk Road to the intersection of Main Street, White Oak Shade Road and Farm Road, was laid out in 1810 after New Canaan had for some years resisted a petition by Norwalk for a road from Norwalk harbor to New Canaan meeting-house. A suit brought in the Connecticut Superior Court was decided in Norwalk's favor. In 1810 the road was laid from Main Street to the town line at the foot of Carter Street, but when New Norwalk Road was built, this eastern end of the old road was somewhat altered and became part of the new highway. The older road for years was known simply as the Norwalk Road or Norwalk-New Canaan Road. (Source: New Canaan Historical Society)


    Old Rock Lane

    Running easterly from White Oak Shade south of the Merritt Parkway to Weed Avenue in Norwalk, was laid out about 1725, the great rock, which lies a short distance beyond the New Canaan line, being mentioned in early surveys. For a time the road was known as Millard Street. (Source: New Canaan Historical Society)


    Old Stamford Road

    Now running from the intersection of the Park and Bank Streets to the Darien line south of the Merritt Parkway and Talmadge Hill Road, begins at Bank Street as a part of the ancient "path that goeth to meet the Perambulation Line," the extension of present Lapham Road as laid out by Stamford in 1700. At the junction with Lapham Road, Old Stamford Road bends to the southwest, and this stretch leading to the junction with Weed Street was laid out in 1834, to connect Lapham Road with the old road continuing south from the present end of Weed Street (then called the road to Ridgefield). (See Weed Street.) After this diagonal hook-up was completed, the highway was considered to be one road and was called Stamford Avenue. The named was changed to Old Stamford Road in 1935. (Source: New Canaan Historical Society)


    Olmstead Court

    Dead-ending westward from Millport Avenue, was developed in the 1930's by the late George McKendry on property formerly owned by Lewis Olmstead of Lakeview Avenue who in the nineteenth century had been a partner of Justus Hoyt in the near-by mill on Five Mile River. (Source: New Canaan Historical Society)


    Orchard Drive

    Running east and west from South Avenue to Old Stamford Road, was developed in 1946-48 through the old Farity orchard. (Source: New Canaan Historical Society)


    Orchard Lane

    Dead-ending northward from Woodland Road, was opened in 1948. (Source: New Canaan Historical Society)


    Osborn Lane

    Dead-ending eastward from upper Valley Road, was called WIlliams Road when it was opened in 1957 and then took an old family name long familiar in the area. (Source: New Canaan Historical Society)


    Overlook Drive

    Dead-ending westward from White Oak Shade Road, was opened up in 1953-54 and took a geographical name although it runs over land that once belonged to Selleck Y. St. John, New Canaan banker, merchant, post master, and town clerk. (Source: New Canaan Historical Society)


    Parade Hill Lane

    Dead-ending westward from Oenoke Ridge as an extension of Parade Hill Road, was opened in the 1930's and from 1938 to 1948 was considered a part of Parade Hill Road. (Source: New Canaan Historical Society)


    Parade Hill Road

    Winding eastward downhill from Oenoke Ridge to the intersection of New Norwalk Road and Forest Street, was a crossroad to the mill on Five Mile River long before the lower end of Smith Ridge was built and probably before Canaan Parish was founded in 1731. North of its western end was the old parade ground, which the road name commemorates. Here, from the founding of Canaan Parish, the train band assembled twice a year for drill until it became the 9th Company of the 9th Regiment of the Connecticut Militia during the Revolution. During the war, it was here that the home guard assembled for the alarms sounded by three shots from a gun. In after years, neighboring landowners enroached on the parade ground and on the old first burying ground, also north of the road and also probably antedating 1731. When there was no longer a military company to claim title to the parade ground, this ancient landmark was lost to the town. The road for years was known as Johnny Jones Lane, a great spot for coasting, because Mr. Jones owned the house on the southeast corner at the Oenoke Ridge end. (Source: New Canaan Historical Society)


    Parish Lane

    Dead-ending southward from Parish Road, was developed in 1954-56. (Source: New Canaan Historical Society)


    Parish Road

    Dead-ending southward from Frogtown Road, was laid out in 1953. The road ends at the south just above the great rocks called "Ye Clefts" as a landmark in many early records, and the branch of the road runs on to the upper part of "Mary" or "Merry" Hill. The name was given to the road by the developer, recalling the time when New Canaan was a parish of the Congregational Church. The road was extended northward from Frogtown Road in 1959. (Source: New Canaan Historical Society)


    Park Place

    Now running southward from Old Stamford Road to Farity Drive, was opened in 1934 as a dead-end road and named because Park Street begins a few feet to the east. (Source: New Canaan Historical Society)


    Park Street

    Running from the intersection of Old Stamford Road and Bank Street to the intersection of Main Street and Oenoke Ridge at God's Acre, was laid out in 1738 by the Proprietors of Norwalk in answer to a petition from the Norwalk members of Canaan Parish for a convenient way to the meeting-house. It began at the Perambulation line at Deacon Bouton's field (where present Bank Street begins), ran along the "west side of White Oak Shade Ridge," and ended below the meeting-house, which stood on the brow of the hill at the present intersection of Park Street and St. John Place. Thus Park Street, together with Haynes Ridge (Oenoke Ridge), White Oak Shade Road (present Main Street), the Brushy Ridge Path to the Meeting-house (present Locust Street), and present Seminary Street, made up the five "spokes" of the wheel that had the meeting-house as its hub. After the present third church was built in 1843, Park Street was extended to the Main Street-Oenoke Ridge intersection. The name Park Street came into use after 1850 when the gravestones on God's Acre were moved to Lakeview Cemetery and God's Acre was called a "park." (See the map on page 110). (Source: New Canaan Historical Society)


    Parting Brook Road

    Dead-ending south from Mariomi Road, was developed in 1955-58 and named for near-by Parting Brook, which "parts" New Canaan and Wilton in that area. It was said by an old resident in 1916 that this was an early road, but nineteenth-century maps do now show it except, possibly, as a part of old Cheese Spring Road (which see). (Source: New Canaan Historical Society)


    Partridge Road

    Dead-ending westward from Mariomi Road, was developed in 1954-58 and named because of the thick cover for partridges. (Source: New Canaan Historical Society)


    Pepper Lane

    Dead-ending north from Ferris Hill Road, was opened up in 1959. (Source: New Canaan Historical Society)


    Phesant Drive

    Dead-ending northeastward from Thayer Pond Road, was developed in the late 1950's. (Source: New Canaan Historical Society)


    Pine Street

    Running east and west between Park Street and Grove Street, was cut through in 1949-50. It was given to the Town by the New Canaan Development Company, which planted pine trees along the way at that time and chose the name to Pine Street. (Source: New Canaan Historical Society)


    Pinney Road

    Running northwest from the intersection of Oenoke Ridge and Lukes Wood Road to continue past the New York State line into Pound Ridge, is probably an ancient crossroad, but its history need further research. In at least one deed it is referred to as a "country" road or post road (see under Old King's Highway), and a record of the attack on Pound Ridge says that one party of Britishers fled "down the road to Canaan." The section of the road from Selleck's Corner (where Barnegat and West roads meet Pinney Road) westward to the state line was laid out by New Canaan in 1828, perhaps over the old right-of-way. Called Pound Ridge Road for years, the present road name commemorated Henry August Pinney, whose shoe factory, built in 1870, stood on the south side of the road just west of Pinney's Corners, the Oenoke-Lukes Wood-Pinney intersection. (Source: New Canaan Historical Society)


    Poconock Trail

    Running west from Comstock Hill Rod, is a 1960 development. The name, chosen by the developer, is a variation of Poquonnuck, the old name for Stratford, Conn., derived from the local Indian tribe. The Historical Society recommends that residents of this very rew road consider changing the name to Old Boundary Lane, because Comstock Hill Road was a part of the Canaan Parish southern boundary in 1731. (Source: New Canaan Historical Society)


    Ponus Street

    Running northwestward from the town line at West Cross Road to Trinity Pass Road in New Canaan's northwest corner, parallels roughly the New Canaan-Stamford boundary. An ancient highway was laid out by the Proprietors of Stamford in 1709 along the path called Ponasses (or Ponuses) Path where the Indian sagamore Ponus supposedly had his lodge. From the present northern end, it originally wound beside the Mill River over land now covered by the Laurel Reservoir, which also buried the settlement called Dantown. The name originally applied generally to the path from its northern end as far south as the turn-off called Davenport Ridge, where Hequets (Hequets Heckett's) Hill and path began, but it was sometimes applied to the whole area. There is no clue to the origin of the name Hequets, and no signature on any deed resembled such a name. One student of Indian tongues has suggested that Hequets is a word or name descriptive of the hill. That Ponus had more than one path is evident from the crossroad farther south referred to as Ponus's "runnet path" and the long road in Norwalk often given in very early deeds as Ponasses Path (now called Ponus Avenue). Ponus was dead before 1667, and Stamford Proprietors took no interest in perpetuating Indian history so many misconceptions gave grown up. Ponus was one of the Indian chiefs who in 1640 deeded to the settlers of Stamford huge tracts of land that included the western third of New Canaan (see more under Oenoke Ridge). (Source: New Canaan Historical Society)


    Prospect Place

    Running northward from Seminary Street, past the western end of St. John Place to a circular dead end to the west, was blasted out of a rack ledge about 1907 by the late Bernard Woundy. While the area was known locally as "Woundyville," the road went nameless until about 1913 when Prospect Street changed its name to St. John Place and Mr. Woundy's son Ira coined Prospect Place. (Source: New Canaan Historical Society)


    Ramhorne Road

    Dead-ending northwestward from West Hills Road, was built in 1952-55 as West Hills North. Later a resident had the name changed to that of the Indian chief of North Castle, N.Y., who with Katonah and representatives of other small Indian tribes did sign quit claims to land in this area. (Source: New Canaan Historical Society)


    Raymond Street

    Dead-ending southward from East Avenue between Burtis Avenue and Hoyt Street, was opened up by the late Mrs. Annie Hoyt Raymond as the last of three roads cut through the old Hoyt Farm. (Source: New Canaan Historical Society)


    Reeder Lane

    Dead-ending south from West Hills Road, was opened in the late 1950's by Dr. John P. Gens, who gave the road his wife's maiden name. (Source: New Canaan Historical Society)


    Richard's Lane

    Dead-ending westward from Old Stamford Road, was opened up during 1925-30 as a private road by the late Dr. and Mrs. George Richards, large property owners along Old Stamford Road. (Source: New Canaan Historical Society)


    Richmond Hill Road

    Running east and west between Park Street and Weed Street, was laid out by the Town in 1854. Its name probably comes from Dr. David Richmond who, from 1800 to 1803, lived near the Weed Street end of the hill. (Source: New Canaan Historical Society)


    Rippowam Road

    Dead-ending eastward from upper Ponus Ridge, was opened up in 1947. Near by is the east branch of the Rippowam River -- hence the road name. (Source: New Canaan Historical Society)


    River Street

    Running north and south from Brushy Ridge Road to Smith Ridge near Strawberry Hill, is an old highway to the mills, the route of which was changed in 1860 after lower Smith Ridge Road was built. (Source: New Canaan Historical Society)


    River Wind Road

    Dead-ending off Lake Wind Road, was built in 1957 not far from Rippowam River, which presumably accounts for the name. (Source: New Canaan Historical Society)


    Riverbank Court

    Dead-ending eastward from lower Parade Hill Road, was a 1953-54 development on the bank of Five Mile River -- hence the name. It's not far from the site of the old natural swimming pool that children called "the Glory Hole." (Source: New Canaan Historical Society)


    Rocky Brook Road

    Is a 1960 road being developed from Cheese Spring Road into Wilton. (Source: New Canaan Historical Society)


    Rocky Nook Road

    A private road dead-ending northward from Lukes Wood Road across the New York State line into Pound Ridge, was cut out about 1932 by J. R. Krapowicz and named by the original residents because rocks are everywhere. On Mr. Krapowicz's property is a natural rock with an elephant's head and the face of George Washington. (Source: New Canaan Historical Society)


    Rosebrook Road

    Running north and south between the top of Brushy Ridge and upper Canoe Hill Road, was laid out by Norwalk Proprietors in 1744 through land that Caleb Benedict bought from David Monroe (Manrow, Munro) whose various properties were often referred to as "Roe's." The brook was sometimes called Roe's Brook and at least once as "ye Gret BRooke running to the Five Mile River." Confusion as to the origin on the name seems to have been caused by the coincidence of there having been a "Roe's Swamp" that was covered with a growth of wild roses. (Source: New Canaan Historical Society)


    Rural Drive

    Looping southward from Parade Hill Road near the Oenoke Ridge end to return to the same road near its Smith Ridge end, was a 1958 development. (Source: New Canaan Historical Society)


    St. John Place

    Running west from Park Street to Prospect Place, was developed in 1888-89. Called Prospect Street until about 1914, it was renamed St. John's Place for the Samuel St. Joh farm through which it ran. Recently, at the request of residents, its name has become St. John Place. The church green originally came down to the east corner of St. John Place where the first meeting-house was built party on land now crossed by Park Street. St. John house, which burned in 1875, had housed New Canaan's first post office. The fire also destroyed many old church and town records that the St. Johns were storing. (Source: New Canaan Historical Society)


    Selleck Place

    Dead-ending northward from Woodland Road, was opened in 1948 and named for Herman Selleck, who had lived at the southeast corner of Woodland Road in a house facing Main Street. (Source: New Canaan Historical Society)


    Seminary Street

    Running west from Park Street to the foot of Elm Street hill, was laid out in 1738 by Norwalk Proprietors from the first meeting-house to the Perambulation Line to meet Stamford's road coming down the hill. The Perambulation Line crossed about where Kimberly Place now begins. Called Brook Street in the nineteenth century because it crosses three brooks, the road was renamed Seminary Street about 1870. Over the years at least five public and private schools have been located along the road, but Mrs. Ayres' Seminary, which was located in the Herbert Scofield house, was not formed until after the road name had been changed. (Source: New Canaan Historical Society)


    Shadow Lane

    Running north from Dabney Road, is a 1960 highway along old Silvermine Hill. (Source: New Canaan Historical Society)


    Shady Knoll Lane

    Dead-ending northward from Jelliff Mill Road, was developed and named in 1955-56. (Source: New Canaan Historical Society)


    Shaker Road

    Running west from New Norwalk Road to Old King's Highway (No. 1), was laid out in 1953 through Hoyt Nursery property. Prior to 1837, one section of the present nursery had been the farm the Stephen Fitch sold to the Shakers, who did not have a religious community here, but the road does not cross the old Shaker farmland. (Source: New Canaan Historical Society)


    Sheridan Drive

    Dead-ending eastward from Briscoe Road near the Vista line, took the surname of one of its developers in 1956-58. (Source: New Canaan Historical Society)


    Sherwood Lane

    Dead-ending north from Wellesley Drive, was built in 1956-58 and named for one of its developers. (Source: New Canaan Historical Society)


    Silver Ridge Road

    Running southwest from Buttery Road, was opened as far an Inwood Road in 1956-57 and extended to Betsy's Lane in 1958. The name was chosen by an out-of-town developer. (Source: New Canaan Historical Society)


    Silvermine Road

    Is an extension of Silvermine Avenue in Norwalk, the highway for the homesteaders along Silvermine River, first called the West Branch and later the Elm Branch of the Norwalk River. From the old mill where the present Silvermine Tavern and now stands, the road turned west to the point where the New Canaan line crosses and our Silvermine Road begins. The first irregular boundary for Canaan Parish as established in 1731 listed as the first landmark a house a short way west of present Silvermine Tavern where John Kellogg was then living. In those days the Silvermine Road was called the Huckleberry Path or the Whortleberry Path, indicating a profusion of those bushes. From Comstock Hill Road, Silvermine Road runs northwest to the point where the original long road becomes Valley Road. There the road turns west at the old Crofoot corner over what was originally a road to Canoe Hill. At the triangle at the north end of Carter Street, Silvermine Road bends off southwestward along a connecting link laid out in 1865 and then follows a section of the old "Clapboard Hill Path to ye meeting-house" and ends at New Norwalk Road. (Source: New Canaan Historical Society)


    Skyview Lane

    Dead-ending southward from Davenport Ridge, was built and named in the early 1950's. (Source: New Canaan Historical Society)


    Sleepy Hollow Road

    Dead-ending northward from Laurel Road not far from Turners Hill Road, was developed in 1952-53 and the name chosen by the contractor. (Source: New Canaan Historical Society)


    Smith Ridge Road

    Running south from the New York State line at Vista to the intersection of New Norwalk Road and Parade Hill Road, was laid out in two sections. The upper part is the older by some 150 years, as it was laid out before 1710 as an extension of Canoe Hill Road, winding around the slope of "Smith's Hog Ridge" and turning north along its western side. Like "Marvin's Hog Ridge," this name indicated that the ridge was used by the Smiths as a feeding ground for their hogs in the first years of their ownership of the land. There is no doubt that the highway followed an ancient Indian trail to the northern hunting grounds, as shown by the early discovery of hollows in the rocks near the Oblong line that had been used for grinding corn and boiling pots. After Country Club Road was laid out in 1734, Smith Ridge Road was used by travelers going from both Stamford and Canaan Parish to Ridgefield and is called the "road to Ridgefield" in deeds well into the 1900's. The "new Smith Ridge Road," from Country Club Road south to Parade Hill Road, was a much-needed extension laid out in 1859. In the early days of the Parish there was a cartway from Country Club Road referred to in various land records as "Bouton's path to the meeting-house," but more research is needed to establish where this ran. (Source: New Canaan Historical Society)


    Soundview Lane

    Dead-ending eastward from Laurel Road, was opened in 1956-58 and named for its view of Long Island Sound. (Source: New Canaan Historical Society)


    South Avenue

    The first block from Elm Street to Cherry Street was laid out in 1856. In that same year it was voted to extend the road, which was finished by 1860 and called Broad Street. It ran then to the present Gerdes Road, generally known as the Road to Darien from White Oak Shade. (See under Darien Road.) After 1860 South Avenue was referred to as the "New Road" to Darien and as the "Two-mile Road." It was popular road for horseracing. After the Merritt Parkway was put through, South Avenue was extended over the Parkway to meet what was left of the western end of Darien Road. (Source: New Canaan Historical Society)


    Spring Water Lane

    Dead-ending north from Jelliff Mill Road, follows a very old driftway through Stevens' land to the fulling mill in existence from about 1725 and in later years to the distillery that caused Weed Street to be known locally as Whiskey Street. The lane was always called the Driftway Lane or Road until the name Spring Water Lane was given it in 1949. It was extended in 1952 and 1957. (See Driftway Lane.) Another driftway leading to these mills from Weed Street was ordered abandoned by Stamford in 1783. These mills stood in the area above the present spur called Driftway Lan. (Source: New Canaan Historical Society)


    Strawberry Hill Road

    Running south and then sharply west from Garibaldi Lane to Smith Ridge, was probably first used as a crosspath or driftway for the convenience of farmers on Brushy Ridge going to the mill at the foot of Smith Ridge. When and why the road got its name will take further research. (Source: New Canaan Historical Society)


    Summer Street

    Running southward from near the intersection of Locust Avenue and New Norwalk Road to Lakeview Avenue, is an eighteenth-century highway, which is probably the lower part of an early cartway coming all the way from Country Club Road (see under Smith Ridge Road). Between Locust Avenue and East Avenue there were lanes leading off to a bark mill and a saw mill. At the south end was "Hanford's Path to the Mill," present Lakeview Avenue. On the 1867 map Summer Street is called Ravine Street. The reason for its present name is unknown. (Source: New Canaan Historical Society)


    Sunrise Avenue

    Looping eastward from Marshall Ridge Road and back to that road again, was laid out in the 1930's. Overlooking Mead Park and the ridge beyond (White Oak Shade Ridge), it does not have a fine view of the sunrise. (Source: New Canaan Historical Society)


    Sunset Hill Road

    Running south from West Road just west of the site of the first Episcopal church, winds southwestward to Weed Street. Opened up by the late Miss Ruth Child in the 1930's, the road runs through former Chichester land that had been purchased by her father, Lewis P. Child, in 1893. Miss Child informed present property owners on Sunset Hill that the Indian name for the hill was Wsigaunota (meaning sunset), according to papers in her father's possession. Search for Indian names was common around 1890, but it is impossible to find this word in any of the Algonquin tongues. The same disappointment meets any searcher for the name Wampanaw given to the old Mill Pond on East Avenue. (Source: New Canaan Historical Society)


    Talmadge Hill Road

    Running eastward from Old Stamford Road to the New Canaan-Darien line on Mansfield Avenue south of the Merritt Parkway, was laid out by Stamford before 1730. It lies partly on the boundary line between New Canaan and Darien in the settlement of which New Canaan gave Darien a strip of land on condition that the highway be maintained by Darien. It is now maintained by New Canaan under an arrangement with Darien. Through the years it has been called the Hill Road, Smith Road, and Chapel Road because of the little church which has served the surrounding area for many years. The present named preserves a regional name that originated in an old family name. (Source: New Canaan Historical Society)


    Thayer Drive

    Running southwestward from Valley Road opposite Huckleberry Road to end in Wardwell Drive, was developed about 1950 through land owned by the late H. B. Thayer (see under Wardwell Drive). (Source: New Canaan Historical Society)


    Thayer Pond Road

    Dead-ending eastward from Mariomi Road, was built in the 1950's an takes its name from the same Mr. Thayer. (Source: New Canaan Historical Society)


    Thruton Drive

    Dead-ending eastward from Ponus Street near the Ponus Monument, was developed in 1953-56 through farmland on the late Samuel Thurton, a former selevtman and a noted grower of giant pansies. (Source: New Canaan Historical Society)


    Toby's Lane

    Dead-ending northwestward from upper Ponus Street, was built in 1946-49 and named for a son of Nixon Griffis, one of the developers. (Source: New Canaan Historical Society)


    Tommy's Lane

    Dead-ending southward from Farm Road, was opened in 1956-58 and named for Tommy Kavanewsky, a son of one of the developers. (See under Farm Road.) (Source: New Canaan Historical Society)


    Toquam Road

    Dead-ending westward from Chichester Road, was built in 1950-52 and named for the area over which the Indian sagamore Ponus ruled and which he sold in 1640 to Capt. Nathaniel Turner as agent for the New Haven Colony. The best guess by Dr. John Huden, authority on Algonquin tongues, is that Toquam means "white rock." The name was given in some deeds to Toquomske, which would mean "where the white rock is." There were two such landmarks in Ponus's lands, one being the "Clefts" west of Weed Street, and the other the high rick on Greenley Road. The names of the two near-by roads, Myanos and Wascussue, are not so suitable to the area as Toquam is. (Source: New Canaan Historical Society)


    Town Road

    New Canaan has two roads so named, both built by the Town. No. 1, running west from New Norwalk Road, passes the highway department garage to join Lakeview Avenue at the northeast corner of Lakeview Cemetery. No. 2, a few yards father south, runs southward from New Norwalk Road and then turns westward to end at Main Street south of Lakeview Cemetery. (Source: New Canaan Historical Society)


    Trinity Pass Road

    Most of this road lies in Pound Ridge and a part in Stamford. But in the 1920's when Sally Anne Lane in the northwestern corner of New Canaan at the upper end of Ponus Street was fenced off, because it ran through the farm of George T. Bye, a short section of new road was laid to connect up with Trinity Pass Road. Trinity Pass Road takes its name from Trinity Lake in Pound Ridge, where three small ponds were developed into a Stamford reservoir in the nineteenth century. Sally Anne Lane ran directly on the Eighth Mile Line. (Source: New Canaan Historical Society)


    Turner Hill Road

    Running east and west between Laurel Road and Valley Road, in the eighteenth century extended along what is now the southern end of Laurel Road to meet Canoe Hill Road. When the Town had to survey and repair it in 1869, the highway was referred to as Mrs. Denslow's Hill. The Turners were turn-of-the-century residents. Seesawing back and forth in modern times, the road name became Turner Hill in 1937, Denslow Road in 1942, and Turner Hill Road in 1956. (Source: New Canaan Historical Society)


    Turtleback Road

    Was cut westward from upper Oenoke Ridge in 1947-49 and extended to West Road above Dan's Highway in 1956-57. Near the western end are two dead-end spurs, Turtleback East and Turtleback West. This road crosses over historic Canaan Ridge and ends on West Road (the old Road up Canaan) just east of where the Perambulation Line crossed the East Branch of the Mill River. (Source: New Canaan Historical Society)


    Urban Street

    Connecting Hillside Avenue with Ledge Avenue east of New Norwalk Road, was laid out in 1913 (see under Brook Street) and named at that time for reasons now unknown. It was not named for Ernest Urban, New Canaan's first World War II casualty. (Source: New Canaan Historical Society)


    Valley Road

    Running north from the old Crofoot Corner all the way to North Wilton Road at Grupe's Reservoir, is the upper part of a long highway from Norwalk laid out for use by farmers and millers living and working along the Silvermine River, originally called the West Branch (later Elm Branch) of the Norwalk River. Therefore in early days it was a part of the Huckleberry (or Whortleberry) Path. (See Silvermine Road.) (Source: New Canaan Historical Society)


    Village Drive

    Running north and south between Farm Road and Field Crest Road, was developed and named in 1956-58. (See Farm Road.) (Source: New Canaan Historical Society)


    Vitti Street

    Running east from Baldwin Avenue to Summer Street, was planned in 1934 to go through land bough about 1926 by Peter Vitti, but only the western section is a town road. The eastern end is almost impassible. (Source: New Canaan Historical Society)


    Wahackme Lane

    Dead-ending northward from Wahackme Road, was called Wahackme Woodland Lane when it was opened in 1946, taking its present name a year later. (Source: New Canaan Historical Society)


    Wahackme Road

    Running east and west between Weed Street and Ponus Street, was laid out in 1752 by Stamford on petition of residents in the area and called by the general name "highway" until the name Chichester Avenue came into use and was so listed in the 1888 Directory. The change to the present name Wahackme was instigated by Mrs. L. Dade Alexander (nee Orline St. John, daughter of Newton St. John), who moved to New Canaan from Alabama in the late nineteenth century. The spelling of the name still stirs occasional controversy. As late as 1908 the name appears on the town records as Mackemo, which was the name of an Indian sachem who was a singer of the deed to Roger Ludlow of the land between the Norwalk and Saugatuck rivers. Since Mrs. St. John was under the impression that she was naming the road for a son of Katonah and that Katonah was a son of Ponus, it is possible that she misread the name Wahackme erroneously given by the Reverend Mr. Selleck as a son of Katonah in his History of Norwalk. Wachamene was one of the co-signers with Katonah to a Westchester deed, but he is not given as a son of Katonah. As far as the name Wahackme is concerned, many Indian names were spelled in various ways according to how they sounded to English ears, and argument about this one seems pointless after its usage for over sixty years. This statement is made only to clear the record and not to recommend a change at this late date. (Source: New Canaan Historical Society)


    Wakeman Road

    Running northward from Lukes Wood Road to the end of Mud Pond, is much the older of the two old roads leading to the mill site. (See Ogden Road.) It is named for present residents on the road. (Source: New Canaan Historical Society)


    Wardwell Drive

    Running east and west off Thayer to two dead ends, was built during 1947-51 as Noble Drive. In 1954 it was renamed Wardwell Drive, for the Wardwell family who had lived on Valley Road beginning in 1833 when Issac Wardwell bought the old Comstock mill on Silvermine River. (Source: New Canaan Historical Society)


    Wascussue Court

    Dead-ending westward from Chichester Road, was built in 1950-52, one of three roads in this section having Indian names. Wascussue was sagamore of a small tribe with lands extending northward from Shippan on the Sound, where he had his village. He was a joint singer with Ponus of the 1640 deed to Capt. Nathaniel Turner, agent of the New Haven Colony. He evidently removed to a point west of Greenwich, because his name appears on a much later deed as sagamore of the Wappings. This was the name of the Indian confederation to which all the tribes in the Stamford-Greenwich area belonged. (See also Myanos Road, Toquam Road.) (Source: New Canaan Historical Society)


    Weed Street

    Running north from Old Stamford Road to West Road, is an ancient highway extending through both the Stamford and Norwalk sections of the old Canaan Parish. As originally laid out in 1699-1700, it began at the traffic stanchion in the road beside the Glenbrook Station and ran north over the Shittim Planes, named for the shittim, or acacia, trees, which grew abundantly on these plains. This was the wood from which the Biblical Ark was made. This section is now called Hoyt Street below our border. The highway was ordered extended to the Perambulation Line, with the northern end to be "accounted large for a driftway." In 1721 the whole road was surveyed up to the Perambulation Line, a little south of the present juncture with Sunset Hill Road. It was when called the Road to Ridgefield, the reason probably being the placing of that town in the Stamford Probate division. From the Perambulation Line, Norwalk built the road along the line to where West Road crossed the Norton River. However, in 1764 the Norwalk stretch of the road was changed to run as it does today. The section from Hoyt Street to the present beginning of Weed Street was given a change of name after the road joining Lapham Road and Weed Street was laid out, and the old south end of Weed Street (to Hoyt Street) is now Old Stamford Road. The Weed family owned considerable land along the road, which explains the present name. The lower end of present Weed Street was sometimes called Stevens Street for the several Stevens families there, and for a time around 1980 the derogatory name Whisky Street was common, because of a well-patronized distillery (see under Spring Water Lane). (Source: New Canaan Historical Society)


    Wellesley Drive

    Running northward from Greenley Road to Woodbridge Drive, was a 1956-58 development. (Source: New Canaan Historical Society)


    West Cross Road

    Connecting Hawks Hill Road with Ponus Street south of the Merritt Parkway, was developed in 1951-55. (See East Cross Road.) (Source: New Canaan Historical Society)


    West Hills Road

    Dead-ending west from West Road, was built in 1948-50 with two spurs, West Hills South and present Ramhorne Road. It was named by the late Llewellyn Ross, one of the developers, for the land it crosses. (Source: New Canaan Historical Society)


    West Road

    Running west from Oenoke Ridge to the Norton River, then northwest across the Rippowam River, and then bending eastward across Pinney Road to continue as Barnegat Road through Pound Ridge, is another of the very old north-south roads. The oldest section, from the juncture with Greenley Road, was ordered laid out by Stamford as a continuation of Greenley Road (which see) in 1709, to run four rods west of the Perambulation Line up to the Eight Mile Line or New York border. For some reason, it was ended quite a distance short of that line, and thus the road was continued by Norwalk up to the border. The lower end, running from the Norton River to Oenoke Ridge, was laid out by Norwalk in 1722, giving credence to the belief that is was then the continuation of the Road to Ridgefield, which was a joint project of Stamford, Norwalk, and Ridgefield. This southern section became the site of the first Episcopal church. Farther east on the north side of the road was "the parsonage land," granted by the Norwalk Proprietors in 1743 to Canaan Parish in fulfillment of their promise of 1728-29 of land "about the White Oak Shade for the use of a dissenting Presbyterian or Congregational Minister." these six acres were sold in 1746 to the second minister of Canaan Parish, the Reverend Robert Sillman, by the committee of the Parish, the price evidently being covered by the grant to him of a hundred pounds at the beginning of his pastorate. He bought adjoining land and supposedly lived there, as he did not buy his twenty acred below Seminary Street until 1767. Quite naturally, this part of West Road was often called Church Hill. The whole road was called West Street until well into the twentieth century, but in very early days a stretch of the upper road was called "the road up Canaan," (Source: New Canaan Historical Society)


    Whiffletree Lane

    Dead-ending off Conrad Road, was the prize-winning entry submitted by Roderic S. Leland when the builder had a road-naming contest in 1955. (Source: New Canaan Historical Society)


    White Birch Farms Road

    Dead-ending eastward from South Avenue south of the Merritt Parkway, was built about 1950. (Source: New Canaan Historical Society)


    White Oak Shade Drive

    Dead-ending eastward from White Oak Shade Road, was built in the early 1940's. (Source: New Canaan Historical Society)


    White Oak Shade Road

    Today running north from the New Canaan-Darien line to become Main Street, at the juncture with Old Norwalk Road, originally began in West Norwalk, being a link in the long highway that extended from Five Mile River Landing on the coast over several ridges with varying local names. It extended along the eastern side of White Oak Shade Ridge, the plateau where South Avenue runs, all the way up present Main Street, until it joined the Haynes Ridge Road, now Oenoke Ridge. It was probably a cafrtway long before it became the highway referred to in the boundaries of the lands of the Hanfords from 1722 on. When the site for the meeting-house was established by the committee of the General Assembly on October 26 1731, it was stated to be about twenty rods west of "Canaan Road." From that time on, the highway was referred to by that name until the northern section became Main Street and the southern section adopted the regional name White Oak Shade. Because of the many mills along the Five Mile River, the original cartway was an important highway, leading as it did to Five Mile River Landing. (Source: New Canaan Historical Society)


    Whitney Avenue

    Dead-ending south from Bank Street just east of the end of Park Street, was developed by Dawless & Mead through property formerly owned by Herbert d. Whitney, about 1920. (Source: New Canaan Historical Society)


    Wilton Road

    Only a few feet of this old highway up Hoyts Plains into Wilton lie in New Canaan, east from Valley Road just north of where Silvermine Road turns. (Source: New Canaan Historical Society)


    Winfield Lane

    Dead-ending eastward from Ponus Street near West School, was opened in the mid-1950's and uses a surname in the developer's family. (Source: New Canaan Historical Society)


    Wing Road

    Dead-ending eastward from Ponus Street south of West School, was cut through about 1940 and by Mr. and Mrs. A. Leland Glidden who chose the name because they felt that at the crest of the ridge one could "take wing." (Source: New Canaan Historical Society)


    Woodland Road

    Winding eastward from South Avenue to South Main Street, was laid out in 1912 (see under Elm Place). It is an appropriate name re-calling the old name of the area, Woodlands of New Canaan. (Source: New Canaan Historical Society)


    Woodridge Drive

    Running westward from West Road, was begin in 1956 and later extended to connect with Wellesley Drive. It was named by the developers for the woods and the ridge it traverses. (Source: New Canaan Historical Society)


    Woods End Road

    A private road dead-ending west from Weed Street north of the Elm Street intersection, was opened in the early 1930's by Mr. and Mrs. William L. Helm to run to "Kelly's Woods," which had belonged to Mrs. Helm's father, the late Richard B. Kelly of Weed Street. (Source: New Canaan Historical Society)


    Woodway Ridge Road

    Dead-ending eastward from Ponus Street, south of the Merritt Parkway, was opened up early in the 1950's and named for its view of the Woodway gold course. (Source: New Canaan Historical Society)


    Wydendown Road

    A private road running westward from Smith Ridge to Father Peter's Lane, was built in the early 1950's. (Source: New Canaan Historical Society)