Benjamin and George Doolittle House (1824)

At 366 Main Street South and Doolittle Hill Road in Woodbury is a house built c. 1823-1824 by brothers Benjamin and George Doolittle. The brothers divided the house equally between them, including the basement (the house is on a hill and there is an entrance to it on the left side of the house, not visible in the image above), where Benjamin and George each had a Dutch oven. During the War of 1812, Benjamin Doolittle (1798-1868) was a drummer boy with the New Haven Grays. He became a cabinetmaker, manufacturing chairs in Litchfield, and moved to Woodbury in 1822. He was an active member of King Solomon’s Lodge, No. 7, of Free and Accepted Masons and of St. Paul’s Episcopal Church. From 1854 he ran an express business between Woodbury and New Haven, as well as routes to other points, such as Waterbury. He died en route to New Haven in 1868. The house remained in the Doolittle family until George’s widow, Betsey Collier Moore Doolittle, died in the Blizzard of 1888.