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Chesterfield High School, which stood here from 1908 to 1992, was the successor to Chesterfield Academy, an antebellum school burned by Federal troops in 1865. A new academy, built in 1889, later became Chesterfield School. By 1907 it has three teachers and 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.
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Enrollment grew after 1908, requiring additions in 1918 and 1923 and remodeling in 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 her, a junior high school until 1981, burned in 1992; the gymnasium burned in 2004.
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