Extending along two miles of Main Street (United States Route 6), from Flanders Road in the north to Old Sherman Hill Road in the south, the district represents an architectural cross section of the town history, from the late 17th century to the present.

The early settlement was made along a long-standing Native American trail, now roughly followed by Main Street.

It was incorporated in 1674, and was the mother town for several surrounding communities, achieving its present municipal bounds by 1807.

It was a prosperous agricultural community in the 18th and early 19th century, the period to which much of the town center's architecture dates.

The Glebe House, built in 1740, is also historically important as the site of an early foundational meeting of the Episcopal Church.