Jessie Rupert: “Though Surrounded By Enemies”

Jessie Rupert (New Market Historical Society)

She taught African Americans to read and write when that was against the law. She burned a Confederate flag. She insisted on flying a Union flag in pro-Confederate town. She was the woman who stood in a muddy street and appealed to a Confederate officer’s humanity to provide aid for suffering Union soldiers.

Yes, everyone in the town of New Market, Virginia, knew about Jessie Hainning Rupert. Brave, irrepressible, educated, and feminine – she rocked the traditional, racist, and political views of her town during the Civil War.

Continue reading