Castleton Village was settled in the early 1770s, and Main Street was laid out in 1772 as the principal east-west route in the region. In 1775 the village is where Ethan Allen mustered the Green Mountain Boys for the Capture of Fort Ticonderoga, early in the American Revolutionary War. Castleton College was founded in 1787, and Castleton Medical College was founded in 1818, both located on the south side of Main Street.