Strong Women of Staunton: Mad Anne Bailey

Mad Anne Bailey, A Woman of Courage and Cunning

Anne BaileyShe wore petticoats as well as buckskins, and the Shawnee did not think she could be killed with arrows or bullets.

Anne Hennis, who was born in Liverpool, England, was one of the most courageous and eccentric women in early American history.

Both of her parents died by the time she was 18, so she moved to America to live with family in the Staunton VA area. It was here she met Richard Trotter, an experienced soldier, and frontiersman. They were married in 1765.The couple had one son, William.

Anne led a typical frontier life until her husband was killed in a border militia fight between Native Americans and the settlers.

Some called the battle in which Richard Trotter lost his life the first battle of the American Revolution. Losing her husband was a stark turning point in Anne’s life.

Grief Spurs An Unorthodox Plan for Anne Trotter 

Enraged by her husband’s death, Anne devised an unorthodox plan to avenge it. She would leave her son in the care of a neighbor and go fight the Indians.

Mad Anne Bailey

Picture courtesy of

Incredibly, her neighbor agreed to the plan.

Donning frontiersman dress, she set out to one recruiting station, then another, and another, making fervent appeals to citizens to volunteer their services in the fight against the Indians.

As you can imagine, Anne was a highly unusual sight. She wore buckskin leggings, heavy brogan shoes, petticoats, a man’s coat and hat with a hunting knife in her waist belt, and a rifle slung over her shoulder.

If anyone embodied the pioneer spirit of the 1700’s, it was her. 

Ann recruited for the Continental Army, delivered messages between numerous Army camps during the Revolutionary War, and often traveled by horseback as a courier between Fort Savannah and Randolph. That’s a distance of nearly 160 miles!

How Anne Became Mad Anne Bailey

During Anne’s rides, it wasn’t unusual to encounter the Shawnee. On one such trip, the Shawnee chased her, at which point, she abandoned her horse and hid in a log.

Although her aggressors looked for her everywhere, they could not find her, even though she was hiding in the log they rested on!

Giving up, the Indians stole her horse and left. Once gone, Anne left her log hiding place and crept into the Indian camp at night, and retrieved her horse.

But not without a bit of fanfare.

From a safe distance, Anne shrieked at the top of her lungs a triumphant cry! After that incident, they feared the frontierswoman and only watched her from a safe distance.

They believed she was “mad” or “possessed” and could not be injured by an arrow or bullet.

Living In the Woods, Anne Finds New Love

Anne Trotter Bailey

Picture courtesy of


Anne lived in the woods for several years when she met John Bailey, a member of the legendary Rangers, a frontier scouting group.

Bailey was defending the settlements of Catawba and Roanoke from Indian attacks when the two met. Instead of finding Anne’s behavior offputting, he liked her rough ways.

And on November 3, 1785, they were married. Together, they were quite the frontier pair!

John fought the Indians and Anne worked with settlers, warning them of impending attacks.


Anne’s Famous Ride

In 1791, Anne Bailey was responsible for singlehandedly saving Fort Lee from certain destruction by hostile Indians.

Her 200-mile round trip, a three-day journey, replenished the store of gunpowder for Fort Lee. Packed on her horse, and given an additional mount, she took the ammunition to the beleaguered fort.

Because of her bravery, the attackers were unsuccessful. To honor her, Anne was given the horse she rode during the attack, a beautiful black equine with a blazed face and white stocking feet.

Anne Bailey was 49 years old when she made the ride that would catapult her fame. When John died in 1802, Anne once again left her home and lived in the wilderness for more than 20 years.

Even though she visited friends, she would often sleep outside. Anne continued her work as a mail carrier and express messenger between Staunton, Lewisburg, and Point Pleasant.

Remarkably, Anne reunited with her son, William, when he moved to Ohio. She followed him there and stayed with him until the end of her life in 1825 at the age of 83.

Anne Bailey is just one of the many heroes you’ll find in the Shenandoah Valley. Come stay with us and learn more about the vital men and women who helped to shape our country.