9401 South Congress Street
New Market, Virginia 22844

Last updated on April 2, 2024

Directions from Steptoe Barber Shop to site 10:  

• Just a short way up from the Steptoe Barber Shop, is the Jessie Rupert School, it is 200 feet north and across the street on the left 
• This is private property and there is not stopping at this site

Jessie Rupert was a Scottish woman who moved to New Market, Virginia in her 30s. She was an avid advocate for anti-slavery, anti-racism, and pro-union. In 1869, Jessie Rupert received many to build a school called the Cottage Institute for Young Ladies. However, at night, the school transformed into Woolworth Collage for African Americans, where Ruper taught African Americans in the local community who sought education. The school eventually closed, and the building remained Rupert’s home until she died in 1909.

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Site 9

Site 11