Chesterfield High School stood here from 1908 to 1992 as the successor to Chesterfield Academy, an antebellum school burned by Federal troops in 1865. A new academy built in 1889 later became Chesterfield School, and by 1907 it had three teachers and so many students in grades 1-11 that a new school was necessary. The 1908 school, designed by E.V. Richards, was a two-story Classical Revival building. Enrollment grew after 1908, requiring additions in 1918 and 1923 and remodeling in the 1950s. A gymnasium was built by the Works Progress Administration in 1934-39. Grade 12 was added in 1948. A new Chesterfield High School on N. Page St. was built in 1969 for students from Chesterfield, Ruby, and Gary in grades 10-12. The old school here, a junior high school until 1981, burned in 1992, and the gymnasium burned in 2004.