It extends mainly along Kirby and Woodbury Roads, and includes a diverse collection of architecture from the 18th to early 20th centuries.

The surrounding area developed agriculturally, and the village center's growth was boosted by the founding in 1850 of The Gunnery, a private boarding school still in operation today.

In the late 19th century the village character began to be shaped by a growing number of summer residents.

[2] The historic district covers an irregularly shaped area of about 85 acres (34 ha), whose principal focal elements are the triangular town green and the campus of The Gunnery.

A significant number of buildings in the district were designed by Ehrick K. Rossiter, an architect who was a graduate of the Gunnery.