The block was built in 1895-96 by Alexander Keith Ritchie, a Scottish immigrant who was operating a dry goods business in Bennington's central Putnam Block. Commercial development was extending eastward along Main Street, and Ritchie had purchased the lot (with a residence on it) in 1891. The house, an impressive Greek Revival structure with temple front, was turned around and moved back in the lot, and now faces Union Street. The upper floor of Ritchie's block was designed for use by the local Masonic lodge, which occupied the space until 1911. The space was occupied through the 20th century by a succession of fraternal and social organizations, including the Elks and the American Legion.
