Round Schoolhouse

The Round Schoolhouse is a one-story circular brick building in Brookline with five windows arranged around its perimeter and a shallow conical roof. The structure relies on an iron hoop system beneath the roof to support its distinctive round shape.

Built in 1822 by Scottish immigrant John Wilson, it is the oldest brick schoolhouse in Windham County and operated as a school for more than a century. The structure was later repurposed for other community needs after its educational role ended.

The building reflects teaching methods from the early 1800s, when students learned in an open circular space under one teacher's supervision. This design allowed education to happen in a single shared room without separate classrooms.

Located on Grassy Brook Road, the building is visible from the road and its distinctive round shape can be appreciated from the exterior. Access may be limited since it now serves as a historical monument, so plan to view it primarily from outside.

After closing as a school in 1929, the building served as Brookline's town hall until 1989. This second life as a civic center demonstrates how the community valued and reused this historic structure.