Chimney Caps in New Canaan, CT

In 1731, Connecticut’s colonial legislature established Canaan Parish as a religious entity in northwestern Norwalk and northeastern Stamford. The right to form a Congregational church was granted to the few families scattered through the area. As inhabitants of Norwalk or Stamford, Canaan Parish settlers still had to vote, pay some taxes-no income tax, and many other modern taxes did not yet exist-serve on juries, and file deeds in their hometowns. Because Canaan Parish was not planned as a town when it was first settled in 1731, when New Canaan was incorporated in 1801, it found itself without a central common, a main street, or a town hall.

Until the Revolutionary War, New Canaan was primarily an agricultural community; after the war, its major industry was shoemaking. As New Canaan’s shoe business gathered momentum early in the 19th century, instead of a central village, regional settlements of clustered houses, mill, and school developed into distinct district centers. Some of the districts were centered on Ponus Ridge, West Road, Oenoke Ridge, Smith Ridge, Talmadge Hill, and Silvermine, a pattern that the village gradually outgrew.

With the opening of the New York, New Haven and Hartford Railroad to New Canaan in 1868, many of New York City’s wealthy residents discovered the pastoral beauty of the area and built summer homes. Eventually, many of the summer visitors settled year-round, commuting to their jobs in New York City.