[1] Development of Winchester's commercial center of Winsted followed from the opening of a turnpike (now Main Street, US 44).

The elongated green was laid out in 1799 above the west bank of the Still River, with a meetinghouse and tavern (neither surviving) built in the following years.

There are 77 historically significant buildings in the 28-acre (11 ha) district, not including the bandstand on the green, which was built in 1970.

The northern end of the green is visually anchored by the Romanesque First Congregational church, built in 1903.

A 1961 interior renovation had lowered the bank floor's ceiling but recent work in 1980 had restored its height.