During the town's first 125 years, this district was the most thickly settled part of the surrounding area.

The village was selected as the seat of Windham County, when the latter was created in 1726, and prospered from the legal activity around the courthouse that was constructed.

[2] The village green today is bordered by the Congregational Church, the Post Office, a former inn, multiple houses, and the original Greek Revival style Windham Bank (built in 1832), which was converted to the Windham Free Library in 1896.

Windham was the home of two of Connecticut's Revolutionary pioneers, Eliphalet Dyer and Jedediah Elderkin; of craftsman J. Alden Weir; and of legal scholar Zephaniah Swift.

The first volume of Swift's work, A System of the Laws of the State of Connecticut (1795), was the first legal treatise in America and concerns the constitution of the state and differences between English and American common law.