Jessie Rupert School House

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Sometime around 1868, New Market resident Jessie Rupert constructed this building at 9401 Congress Street. The structure, originally three stories tall, served as her residence and a school.

Rupert, born May 15, 1831, had considerable experience providing educational opportunities. During the 1850s she was the Principal of the Ann Smith Academy in Lexington Virginia. In 1858 she moved to New Market to head the New Market Female Seminary which she led until 1867.

Despite this experience, Rupert and her school were not popular in New Market. A unionist during the Civil War, Jesse had faced the hostility of the local populace. When her husband, a local magistrate and community leader Solomon died in 1867, she found herself without the protection his status provided and soon without a job when she was ousted as leader of the Female Seminary.
Undaunted, Jesse Rupert continued her work as an educator. This building would house two separate schools between 1868 and 1870. The first was the “Cottage Institute,” a day and boarding school for young women funded by tuition. Details about this school are sparse, but it appears to have operated from ca. 1868 - ca. 1870.

The second school was the “Woodward Cottage Institute.” It provided both a day and night school, tuition free to local white and African American children. These students typically could not afford tuition to local private schools.
The first reference to this school appears in a December 1, 1869 letter from Rev. Edward Hale to General O.O. Howard appealing for assistance for the school. In the letter, Hale mentions Jessie Rupert was teaching 55 pupils in New Market using funds from the “Soldiers Memorial Society.” Following this letter, Rupert would begin to receive financial assistance from the Freedman’s Bureau and the American Missionary Society for a night school that would last through 1870. She adopted “Woodward Cottage Institute” as the name of the school.

Jesse Rupert provided numerous monthly reports to the Freedman’s Bureau on her work with the Woodward Cottage Institute. A January 20, 1870 report noted she was being paid $20 per month for the night school which was having a positive impact “among the poor here.”
In the same report she described her school building as 80’ x 40’ and two stories high. She conducted school in a 20’ x 35’ school room on the first floor and lived on the second. Multiple classes were offered here for white and black students. It is uncertain if the classes were integrated or if separate classes were offered for each race at different times.

Three months later, Jessie Rupert provided an April 1870 report to the Freedmans Bureau. In it, she noted there were 29 “colored” students and 17 white students who she was teaching alphabet, reading, geography, arithmetic, and writing. She would provide services for an average of 30 students each month that the school operated.

The New Market community was not happy with Jesse Rupert and her school. Many opposed free public education in general and most opposed the idea of white and African American students being educated together. For example, on February 22, 1870 she faced off with local members of the Ku Klux Klan and other white supremacists after flying the American flag outside the school on George Washington’s birthday. A group attempted to enter the school at night to remove the flag, but were blocked by an armed Rupert. In a report to the Freedman’s Bureau the next month, she reported public sentiment about the school was “most bitter” and wrote “I have suffered greatly almost to violence, because of my connection with the American Missionary Association.”

In June 1870 funding for the Woodward Cottage Institute ceased and the school closed. The Cottage Institute also closed around that time in part because local residents boycotted sending their children to Rupert’s school because she had chosen to educate African Americans.

Jessie Rupert would continue to reside here until her 1909 death, supporting herself by becoming a travelling speaker discussing her trials as a Union sympathizer in the south in various northern cities.

This building, as originally constructed contained numerous architectural features that were designed to look like a cottage in line with the school’s name. These were removed or covered during several 20th century renovations.

As of 2023 the building still stands but is unused.