Round Schoolhouse, Historic brick schoolhouse in Brookline, Vermont

The Round Schoolhouse is a single-story circular brick building on Grassy Brook Road in Brookline, Vermont, with a shallow conical roof and five windows. A gabled vestibule projects to the south as the only entrance. Inside, the roof is held by an iron hoop with rafters leading to a central king post that rises through the roof as a finial. The single chamber dates to 1910, with tongue-and-groove flooring and wainscoting.

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.

A plaque on the exterior names the designer, Dr. John "Thunderbolt" Wilson, and records that he taught the first term of 60 pupils who sat on benches. The interior was completely renovated in 1910, and on March 5, 1929 the building was turned over to the Town of Brookline for use as the town hall.

The building stands on the west side of Grassy Brook Road, just south of where the road crosses Grassy Brook and south of Brookline's center. The only entrance is through the gabled vestibule projecting to the south, and the five windows sit in the circular brick wall. It has been a National Register property since 1977, so view it from the roadside.

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.