Dating to c. 1903, the Canfield Building is a historic commercial block at 93-97 Main Street in the village of Canaan. Originally built to house the Canfield Lime Company. It features a pressed-metal exterior and cast-iron storefronts.
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The first Methodist sermon preached in what is now the town of North Canaan was given in 1786 at the Lawrence Tavern (the Isaac Lawrence House on Elm Street). A Methodist church was erected in 1816 and remained in use until the current Canaan United Methodist Church was erected in 1868-1873. It is located at 2 Church Street, at the west end of Main Street where it divides into Church and West Main Streets. The original church building was sold to a farmer. The large stained glass window at the front of the church was installed in 1905. The church merged with the Falls Village Methodist Church in 1966. That church’s first structure, built in 1793, was the first building for Methodist worship erected in the New England states.
The Housatonic Railroad was established in 1836 as a route between Bridgeport and Great Barrington, Massachusetts. A right-of-way for the railroad passed through what is now the Town of North Canaan, where Canaan village would develop around the new railroad station. That original station was in the Warner-Canfield Hotel building, which stood on the east side of the tracks and fronted on Main Street. In 1872, a new Italianate-style train station was erected on the south side of the tracks. Called Canaan Union Depot, it was built as a collaboration of the Housatonic Railroad and a new east-west line, the Connecticut Western Railroad (later acquired by the Central New England Railroad), which intersected the Housatonic line in the center of the village. Both rail lines would eventually come under the control of the New York New Haven & Hartford Railroad. The depot had a large restaurant on the first floor, an important feature in the era before dining cars. Rail service ended in the early 1970s, and the station became a retail center, which included a railway-themed restaurant. Rail service (for freight and excursions, but not regular passenger service, yet) resumed after a new Housatonic Railroad was chartered in 1983. The southeast half of the building, including the original tower, was destroyed by arson on October 12, 2001. The Connecticut Railroad Historical Association purchased the structure in 2003 and began a rebuilding of the historic station, which was dedicated in 2018.
The Operations Center of the Salisbury Bank and Trust Company is located in a brick Colonial Revival building in the Village of Canaan in the Town of North Canaan. The building was erected in 1952 for the Canaan Savings Bank. It replaced an earlier building on the property, called the Cummings Building, that was destroyed by fire. A circa 1905-1910 postcard of that building shows that it then housed the Canaan Post Office, the F.R. Collin jewelry and watch store, and the Canaan Savings Bank.
