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New Canaan’s Shoe Industry


The image is The Shoemakers, printed by E.B. & E.C. Kellogg, lithograph, c. 1855-1856 – Connecticut Historical Society

Stories from New Canaan’s history are endless. As I look at records, and read annuals, I realize how many of the characters’ lives intersect through marriage or business, how generations from the same families stayed and shaped this Town, and how the history of New Canaan sometimes reflects the wider national history and sometimes charts its own course. Such is very much the case in the first workers’ strike that occurred here in 1854. 

Shoemaking was the dominant industry in the 19th century, but wages for shoemakers were quite low. The bosses, including Caleb Benedict, were pressing the jours (journeymen) “to vigorously apply the hammer and hasten the stitches and to hurry up the work,” according to an article by Benjamin Benedict (the youngest brother of Caleb St. John Benedict) published in the New Canaan Messenger on January 1, 1887. So a meeting was called at the Town House (what is now the front portion of the Museum’s offices at 13 Oenoke Ridge.) A large crowd attended, and “good order and sobriety prevailed.” An appointed committee drafted a list of prices on 75 different types of shoe work. This list was then presented to the bosses, who “ridiculed the whole thing.”

A strike was called on a Wednesday. The plan was for all the jours to finish whatever work they had out by Saturday. Whatever wasn’t finished would be turned back into the factories. 

The strikers assembled at the Town House once again. The members of the newly formed Cordwainers’ Protective Union – lasters, sewers, peggers, stitchers, and crimpers- marched through God’s Acre carrying lasts and hides while music played. They delivered the made and unmade shoes. This time, the bosses gave in and improved the wages, and the Union quickly dissolved. 

Benedict describes that he had outstanding six pairs of double soled men’s peg boots, which he did not want to return unfinished. Before the strike, he stayed up for two days straight, hammering each wooden peg into each sole, and finished the boots. He delivered them to his employers at Benedict and Bradley on the day of the strike. The foreman, John Keeler, inspected the boots. As Benjamin tells the tale, Keller said, “’These are nice looking boots. I should think they were made in a strike.’ Said I, ‘You are right, I put into those boots a mighty lot of strikes yesterday.’ ‘Won’t they crawl?’ inquired John. I replied, ‘I guess so, too. You had better put them into a box and nail the lid tight before they show their teeth.’” Historical humor for the peg and the strike at its very best.

I like to imagine the shoemakers of New Canaan assembling in the very building where I work every day, and marching together down the hill with their shoes, tools, and leather. It was clearly a peaceful strike, which was at odds with much of what was happening in other parts of the country, and the parties quickly reached an agreement, which kept the shoe industry operating in New Canaan for the rest of the century.  

Warm regards,

Nancy Geary

Executive Director