The town of Chester, Vermont, is one of the best small towns in the state for architecture lovers! Don’t believe me? I will prove it in this upcoming series. Located in Chester Village, the town’s center, this handsome brick building set off the main street, was built in 1884 as the town’s high school, replacing an 1814 private academy formerly on the site. The private academy closed in 1881, and the building was sold to the town, who by 1884, demolished the original structure and erected the current Italianate style building. The building served as the town high school until 1911, when a new high school was constructed nearby. The elementary and junior high school operated from here until the 1950s, when a modern school was constructed in town. Since 1950, the former academy building has been used by the Chester Art Guild, and currently is leased from the Town by the Chester Historical Society. The structure retains its architectural character down to the segmental arched windows and cupola.