Ann Hennis was born in 1742 in Liverpool, England. Both of her parents had died by the time she turned 18. Ann was poor and had a hard time earning enough money to survive. She made her way to America in 1761 and settled at Staunton, Virginia where she lived with relatives.
Anne was formally educated and learned to read and write in Liverpool, England.
As more and more people moved West, fights broke out between settlers and the Native Americans who already lived in this region. The Governor of Virginia formed border police in order to help calm the area. At the Battle of Point Pleasant on October 19, 1774, Native Americans under the Shawnee Chief Cornstalk attacked the Virginia militia, hoping to halt their advance into the Ohio Country. After a long and furious battle, Cornstalk retreated. The Virginians, along with a second force led by Lord Dunmore, the Royal Governor of Virginia, then marched into the Ohio Country and compelled Cornstalk to agree to a treaty, ending the war. Called the first battle of the American Revolution by some, this conflict prevented the Native Americans from becoming associates to the British. Although the settlers won the battle, there were massive losses on both sides.
After learning that her husband was dead, Anne left her young son in the care of neighbors, dressed in the garb of a frontiersman, and set out to avenge her loss. She rode from one recruiting station to another, making appeals to all she met to volunteer their services to the militia in order to keep the women and children of the border safe, to fight for freedom from the Indians, and later the British.
Although Mad Anne primarily rode up and down the western frontier, she also recruited for the Continental Army and delivered messages between various Army detachments during the Revolutionary War. She often traveled as a courier on horseback between Forts Savannah and Randolph, a distance of almost 160 miles. She was generally known and admired by the settlers along the route.
On her rides, Bailey often came across a group of Shawnee Indians. In one such encounter, Bailey was being chased by them and about to be caught when she jumped off her horse and hid in a log. Though they looked everywhere for her and even stopped to rest on the log, they could not find her. They gave up and stole her horse. After they left, Bailey came out of the log and during the night crept into their camp and retrieved her horse.
When she was far enough away, she began to cry at the top of her voice. The Shawnee thought she was possessed and could not be injured by a bullet or arrow. After this event, they saw her often, but they feared her and only watched her from afar, making her relatively safe living in the woods.
After several years living on her own, Anne met John Bailey, a member of a legendary group of frontier scouts called the Rangers, who were defending the Roanoke and Catawba settlements from Indian attacks.
In 1787, along the Kanawha River at the mouth of the Elk River, a blockhouse was built. Later it would be called Fort Lee in honor of Virginia’s Governor Henry Lee, father of Robert Edward Lee of Civil War fame some seventy-five years later. It was to this fort that John Bailey went on duty, taking with him his now famous, gun-toting, hard-riding bride.
In 1788, John Bailey began duty at Fort Clendenin, where there was more conflict between the settlers and Native Americans. Anne Bailey began working for the settlers as well, riding on horseback to warn them of impending attacks.
In 1791, Anne Bailey by herself saved Fort Lee (now Charleston, West Virginia) from certain destruction by hostile Indians with a three-day, 200–mile round trip to replenish their supply of gunpowder. After hours of riding, she reached Fort Savannah at Lewisburg. There, gunpowder was quickly packed aboard her horse and one additional mount, before she reversed her direction and galloped back to Fort Lee.
With Anne’s return, the siege was lifted, the attackers repulsed.
Anne's most famous exploit was her relief of Fort Lee, which stood where the city of Charleston, West Virginia, afterward arose. The stockade was besieged by Indians, the powder gave out, and it was very dangerous for a courier to get past the assailants. But Mad Ann volunteered, rode swiftly on her horse "Liverpool' to Fort Union - now Lewisburg, - and came back with an extra horse with a fresh supply of powder. This was in 1791 when she was 49 years of age.
Quotations: "I always carried an ax and auger, and I could chop as well as any man... I trusted in the Almighty... I knew I could only be killed once, and I had to die sometime."
As an unmarried "spinster" in eighteenth-century Boston, Bailey possessed the power to control her own fate in a way denied to most married women, but she also had to earn her own living. Both factors probably influenced her attempt to serve in the military, and both factors disturbed government authorities once her disguise was discovered. Whatever the case, Ann Bailey wanted to be a soldier, and she was willing to risk reputation, money, and even imprisonment for the chance to fight.
She earned her nickname as "Mad Ann" because of her hot temper. In addition to dressing like a man, she also was said to have learned to drink and swear like a man.
In about 1765, she married Richard Trotter, who also lived in the Shenandoah Valley. The couple had one child named William Trotter, who was born near Barber, Virginia in 1767.
Ann’s husband, Richard was part of the Virginia Militia when he was killed on October 10, 1774, at the Battle of Point Pleasant in Dunmore’s War, a conflict between the Virginia Colony and the Shawnee and Mingo Indian tribes.
In 1785 she married John Bailey, a frontiersman, and ranger. The two moved to Clendenin’s Settlement on the site of present-day Charleston, West Virginia in 1788. John Bailey died in 1794.
