A legislative act created Chester Academy on October 30, 1814, and it opened on this site on March 13, 1815. A unique hexagonal cupola crowned the Federal-style brick building, and local families financed the school, with the Chester Masons contributing the addition of a third story for lodge meetings. The co-educational academy ranked among the earliest institutes offering secondary-level education in Vermont, with a Classical curriculum attracting 150 or more students annually. Its graduates included college presidents, congressmen, Civil War generals, and a Vermont governor. Enrollment declined as public high schools emerged in the region, and the academy closed in 1873; the building was razed in mid-1881. Behind its site, the present brick building was erected in 1881 for School District No. 20. With its distinctive cupola and Italianate style, it was considered an ornament to the village. Chester’s first public high school opened there on the second floor in 1885, and its progressive curriculum attracted students from outside Chester. Its first female principal was installed in 1891. The Central High School remained there until a larger high school opened on Depot Hill in 1912. The building then served as an elementary school into the 1950s and as the junior high school until 1970, and it is now occupied by the Chester Historical Society and Museum.