Until 1941, the only secondary educational facility available to African-American students in Loudoun County was the upper level of the Loudoun County Training School. The frame structure offered a limited curriculum in an unsafe building. During the late 1930s the black community in Loudoun County organized fundraiser events to purchase 8 acres (3.2 ha) of land on the east side of Leesburg from W.S. Gibbons. The property was conveyed to Loudoun County for $1 on December 16, 1940. After threats of legal action, the school board approved a measure to borrow $30,000 from the State Literary Fund of Virginia to build the school. A bid from the Taylor Manufacturing Company of Farmville, Va was approved for $35,438. The school opened in September 1941. The school was named for African-American abolitionist Frederick Douglass at the request of the community organizers. Since a bare minimum of furnishings were provided by the county, more private donations were sought to more fully furnish the school. With desegregation in 1968 the building became a middle school, then a special education and alternative school.
Douglass High School was placed on the National Register of Historic Places on September 24, 1992.