Located on Main Street, this large brick structure stands as the latest example of Italianate architecture in town. The building was constructed as the consolidated central high school, which sought to bring together secondary school students to a larger school. By 1801, the town of Chester, with a population of just under 2,000 citizens, had 19 school districts, each with its own school building (nearly all being one-room schools). As the population of town became more centered around the developing main street and railroad depot, the central school was constructed. The building served as the town’s high school until 1911, when a larger school was constructed nearby on Depot Street. The building later served as a primary school. By the 1960s, the town had no use for the building, and allowed the newly established Chester Historical Society and Museum to operate the space and showcase the town’s rich history.