The Round Schoolhouse is a historic school building on Grassy Brook Road, across from the Brookline town office. Built in 1822, it is the oldest brick schoolhouse in Windham County, and distinctive for its round shape. From 1929 to 1989 it served as Brookline’s town hall. It was listed on the National Register of Historic Places in 1977.[1]

Description and history

The Round Schoolhouse is located on the west side of Grassy Brook Road, south of the center of Brookline, and just south of the road’s crossing of Grassy Brook. It is a single story circular brick structure, with a shallow-pitch conical roof. A gabled vestibule projects to the south, providing the only entrance to the building, and there are five windows in its walls. The roof is held together by an iron hoop, with rafters leading from the wall to a king post at the center. The post rises through the center of the roof, providing a finial on the exterior. The interior of the school is a single chamber, which originally had benches arranged to face the teacher’s desk, which was located near the door. The interior dates to 1910, with tongue-and-groove flooring and wainscoting.[2]

The Schoolhouse was built in 1822, replacing an earlier wood frame structure that stood nearby. The school was built by John “Thunderbolt” Wilson, a Scottish immigrant who is said to have been a highwayman in his native country, but established a practice as a doctor and teacher, serving Brookline and Newfane. The building was used as a schoolhouse until 1929, when a new school was built that conformed to state standards. The building was then used as Brookline’s town hall until 1989.[2]

Interior Photos:

The only Round Schoolhouse in the country

A plaque on the exterior of the schoolhouse, as of August 17, 2020, reads as follows: “Designed -1821- By Dr. John “Thunderbolt” Wilson. Built in 1822 on this site deeded to the Town of Brookline by Peter Benson, for the sum of $5.00. Dr. Wilson, a former Scottish highwayman, 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. This building is thought to be the only round schoolhouse ever constructed in this country.”[3]

Round Schoolhouse Memorial Garden Brookline Vermont
photos by Laurie Nau-Martocci

Travel Channel “Monumental Mysteries”

In 2014, the Travel Channel filmed a segment for their “Monumental Mysteries” program about Capt. Thunderbolt and the Round School House.

Travel Channel Round Schoolhouse Video

Get involved

Interested in learning more about the maintenance and care of this amazing structure? Get involved with the Historic Round Schoolhouse Committee. We’d love to have your help!