Centered on the junction of Main Street and Academy Road, the district's architecture is reflective of the town's development over two centuries, and includes many of its civic buildings.

[1] The town of Cheshire was settled in 1694 by colonists from adjacent Wallingford, which it remained a part of until incorporating separately in 1780.

The town center arose around the location of the first meeting house, where the First Congregational Church (built 1826) now stands.

It briefly benefited in the mid-19th century from the mining of copper and barite, a time at which it also saw expansion of industry occasioned by improved transportation.

It covers about 35 acres (14 ha), and is predominantly residential, with a significant concentration of houses built before 1850.