When the Windham County courts were transferred from Westminster in 1787, they were housed in the village known as Newfane on the Hill. Four decades later, influential residents convinced their townsmen to shift the village down to their land in a flat part of town, a location better suited for waterpower and commerce and ease of travel in the winter months. The first two buildings constructed were the courthouse and jail on a common. The village center grew rapidly as people moved old buildings down the hill and remodeled them or built anew, establishing a particularly unified townscape. This courthouse building is very stately for such a small town and packs an architectural punch. The two-story building is capped with a belfry and was designed in the Federal style with fan motifs over the windows and door. In the 1850s, nearby Brattleboro tried to usurp Newfane’s county seat status, so they in turn expanded the courthouse, raising the ceiling on the upper floor and adding the monumental Doric portico and pediment to give the building a decidedly Greek Revival appearance.