There is no clear consensus about how Vinegar Hill got its name, but everyone agrees that Charlottesville lost a colorful part of its vital history when this neighborhood was razed in 1962 in favor of urban redevelopment. In the early 1900's the area s treching northward from South Sixth Street across Main Street and Vinegar Hill to Preston Avenue became a predominantly black settlement.

During the 1920's, the principle black business district was located here. Both sides of Main Street were lined with barbershops, poolrooms, furniture stores, grocers, drug stores, professional offices, cleaners, fish markets, and restaurants that served an ecumenical clientele of whites, blacks, townspeople and students. Bustling with activity almost all hour s of the day, the "Hill" is best remembered as a vibrant center of the social life of Charlottesville's black community as well as the heart of its business establishment.