The Winchester Colored School occupied the Old Stone Church building constructed by the city's Presbyterians around 1788. In 1858, it was leased to the Old School Congregation Baptist Church of Color, for $500. The members of the congregation bought 50-cent shares to pay the rent. In 1878, the city's first public school for black children opened here, called the Winchester Colored School. The building was divided into three rooms, heated by a single wood stove. By the 1920's, the building was no longer big enough for all the children enrolled, and in 1924, the black community petitioned the Winchester School Board for a new school. In 1927 the new school, named after the abolitionist Frederick Douglass, was opened, along with a segregated library for African Americans.
Recently, the Old Stone Church was restored as a church and subsequently used for weddings and special services. The Old Stone Church was added to the National Register in 2001.
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304 E. Piccadilly Street