In 1924, the black community petitioned the Winchester School Board for a new school to replace the overcrowded Old Stone Church building. Construction of Douglas School was begun that year, with funds from the Handley Trust, and a parade of 1,000 people, nearly a mile long, celebrated the laying of the cornerstone. Three years later there was another parade as 150 students and six teachers marched from the old school to the new one. This new facility had six classrooms, offices, restrooms with showers, a projection room where movies could be shown, and a branch of the Handley Library for African Americans. The whites-only branch of this library had opened decades earlier, in 1913. Generations of African-American children from Winchester and the surrounding area studied at the Douglas School, which educated children through grade 9; students who desired further education had to go elsewhere. In 1938, of a graduating class of eight, five went to high school in Washington, D.C.: one became a lawyer, one a research biologist, one a psychologist, and one the fire marshal of the District of Columbia.
By 1953, Douglas had become a high school. Additions included more classrooms, an industrial arts shop, a gymnasium, and a cafeteria. In 1966, when Winchester schools were integrated, Douglas became an intermediate school. Later it became the Douglas Community Learning Center, home to the Caretakers, Head Start, and Stepping Stones, all educational programs for young people. In 1999, this building was named an historic landmark on the Virginia Landmarks Register.
The spelling of the school's name is contentious, with some local citizens requesting an additional "s" at the end of the name to comply with the correct spelling of Frederick Douglass' name. Oral historians indicate that Principal Kirk N. Gaskins Sr. dropped an "s" from the name in the 1940s to avoid confusion between the Douglas School and the Douglass High School in Leesburg.
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598 North Kent Street