This unusual round, brick schoolhouse is a testament to the importance of public education when the Connecticut River piedmont of Windham County reached full agricultural settlement between 1820 and 1830. In August 1821, the town purchased a small lot on the main brook road for five dollars, intending to build a replacement for a log schoolhouse nearby. Two members of a building commit tee, Dr. William Perry and Samuel Stebbins, approved a plan by Dr. John Wilson, the immigrant son of a blacksmith from Muirkirk, Scotland. Wilson had been a highwayman in Scotland before escaping to the United States in 1819, but when he settled in Brookline he became a schoolteacher. Wilson's scheme produced a substantial Flemish bond schoolhouse with a conical wood-shingle roof. A small brick porch leads to the main entrance, and the interior is a single room, originally with sixty desks and a central chimney. In 1910 the present floor, two-over-two sash windows, and a woodshed ell were added. In 1929, the school closed and the town hall took over the building, continuing to occupy it today.