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.

Her Life

Jessie Hainning was born on May 15, 1831 – thirty-three years before the Battle of New Market. The youngest of ten children, she came to the United States from Scotland with her family when she was little. Orphaned by the age of seven, Jessie spent her youth in private academies in Massachusetts and Pennsylvania and received one of the best educations available to young women in mid-19th Century.

Single and determined to make her way in the world, Miss Hainning moved from the north to Lexington, Virginia, where she became the principal at Ann Smith Academy which was located near Virginia Military Institute. She opposed slavery, believing in equality for all. Her religious beliefs prompted her to help teach a Sunday School for enslaved in Lexington and she worked with Thomas J. Jackson.

In 1858, Jessie moved north to New Market, Virginia, becoming principal of New Market Female Seminary. There, she met Solomon Rupert – grandson of Solomon Henkel who was a prominent citizen in the town. The Rupert family wasn’t too keen on Solomon’s friendship with Jessie since she was a “Yankee woman.”

When the Civil War began, New Market’s residents actively and enthusiastically supported the Confederacy, but not Jessie. She decided to fly a United States flag at her home. When her neighbors tacked at Confederate flag on her house, she retrieved matches and burned it. Solomon Rupert – the Justice of the Peace – hauled her to the town jail to prevent the angry mob from harming her. Shortly after the incident, Jessie got taken to the new Confederate general in the valley to face judgment for her actions; to her relief, her former friend – Thomas “Stonewall” Jackson – greeted her warmly and helped dispel some of the prejudice against her.

Jessie married Solomon Rupert during the war, and by 1864, they had an infant. Sadly, Solomon died in 1867. Widowed, Jessie needed a way to provide for herself and her children, but her methods again shocked her town. She received aid from the Freedmen’s Bureau and American Missionary Society to open a school for African Americans. On at least one occasion, she armed herself to defend her scholars against the Klu Klux Klan.

In her later life, Jessie toured the north, speaking about her experiences and loyalty during the war. She died in 1909 and is buried beside Solomon in Emmanuel Lutheran Church Cemetery in New Market, Virginia.

Her Home

Both of Jessie Rupert’s homes in New Market stood along Congress Street, which is the main road (and part of the Valley Pike) that runs through town.

Her first residence – also the location of New Market Female Seminary – is at the corner of Congress Street and Seminary Street where the Methodist Parsonage now stands. A small memorial marker at the corner notes the historic school site.

Her second residence is where Jessie taught school for African Americans. That house still stands, but is not a tour-able site. South of her war-era home, this home stands between the modern Mexican food restaurant and Sun Bank.

During The Battle

Jessie and Solomon Rupert believed that it was God’s will that they should help anyone suffering or in need. During the war, they took sheltered both Union and Confederate injured who needed careful tending.

The Battle of New Market on May 15, 1864, ended with a Confederate victory and hundreds of wounded. Since the Union army retreated, many of the boys in blue had to be left behind. While other civilians focused on helping Confederate wounded, there wasn’t much enthusiasm for taking care of “the enemy.” That’s where Jessie stepped in.

She helped to organize shelter for the Union wounded. Solomon used his wagon to bring the badly injured from the battlefields to their makeshift facilities. Soon overwhelmed, Jessie went searching for another building to bring the boys in blue out of the rain and make tending their injuries easier. Her neighbors refused to help. Jessie stood in the muddy street and managed to stop a company of Confederate troops, explaining the entire situation to the captain, who ordered his men to break open a warehouse for the lady to aid the enemy’s injured.

The soldiers of the 34th Massachusetts Infantry were so grateful for Jessie’s care and kindness that they honored her by calling her the “Daughter of the Regiment.” For decades after the battle, she stayed in contact with many of these veterans and even attended some of their reunions.

She Inspires Me

Jessie Rupert has been one of my favorite New Market women to study. I still have questions about her life and legacy and hope to continue to research her remarkable life in the coming months and years.

When I think about why I admire her and see her as role model, here’s what stands out:

• She had a quiet and unbreakable feminine strength – whether it was confronting a mob, appealing to a Confederate officer to aid his enemy, or protecting her students.
• She remained steadfast to her faith and to kindness – it does not seem like she became bitter toward her neighbors and was ready to reconcile when they approached her
• She had the courage to defy local societies to carry out her moral convictions

The minister at her funeral honored her with these words which sum up her life simply: “Here lies one, who famishing fed the hungry; though herself suffering,
gave aid to the distresses; though surrounded by enemies, loved all, and who
lived to hear her former enemies call her The Angel of the Shenandoah.”

Your Historian,

Miss Sarah