New Canaan Now & Then: Main Street and Locust Avenue

The shoe industry dominated New Canaan’s economy for more than a century. The first factory opened in 1768 on Brushy Ridge Road, but by the early 1800s there were numerous factories in the downtown area. At the height of production, New Canaan shoemakers produced 50,000 pairs per year. Five generations of the Benedict family created a shoe dynasty. At times, they employed as many as 100 people.  

The Big Shop located on the corner of Main Street and Locust Avenue was the factory and retail outlet for Benedict & Co. Sadly, the handmade shoes in New Canaan couldn’t keep up with the mechanized means of production in the factories in Massachusetts. By 1924, there were no shoe factories left. In the photo above, the columns of the 1868-built structure at 60 Main St.—known to many as the Knights of Columbus building, present-day home to Chef Prasad restaurant—can be seen through the trees at right. “New Canaan Now & Then” is presented in partnership with the New Canaan Museum & Historical Society.