A Legislative Act created Chester Academy on October 30, 1814, and it opened March 13, 1815 on this site. A unique hexagonal cupola crowned the Federal-style brick building. 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. Among the graduates were college presidents, congressmen, Civil War generals, and a Vermont governor. Enrollment declined with the emergence of public high schools in the region, and the Academy closed in 1873. The building was razed in mid-1881.
District No. 20 Central School
The present brick building was erected in 1881 for School District No. 20 behind the site of the Chester Academy. Displaying a distinctive cupola, the Italianate-style building was considered an ornament to the village. In 1885, Chester's first public high school opened on the second floor. The school's progressive curriculum attracted students from outside Chester. Its first female principal was installed in 1891. The Central High School remained here until the opening of a larger high school on Depot Hill in 1912. This building served as an
elementary school into the 1950s, and then as the junior high school until 1970. The Chester Historical Society and Museum now occupy the former school.