For most women, especially during the Revolutionary War era, life’s losses brought a long time of mourning, the wearing of black dresses, and times of reflection, before they eventually consider remarrying. For Anne Hennis Trotter Bailey, whose lifestyle earned her the name “Mad Anne” for her acts of bravery and heroism that were considered to be somewhat eccentric for a woman of her time, loss brought about quite the opposite reaction. Anne Hennis was born in Liverpool England in 1742. She was formally educated and learned to read and write. Her first experience with loss came before she turned 18. It is not known how they died, but both of Anne’s parents were gone before she turned 18, and she became an orphan. Life for Ann, who was poor and had a hard time earning enough money to survive, immediately became very hard. Anne had family near Staunton in the Shenandoah Valley, and when she was 19, she sailed to America to live with them. There, in 1765, she met and married Richard Trotter, a seasoned frontiersman and experienced soldier. The couple had one son named William.

During the westward movement, when more and more people were heading west in search of land and adventure, fights began to break out between settlers and the Indians who had lived there for many years. The Governor of Virginia organized border militia to protect the settlers there. Richard Trotter joined this militia. On October 19, 1774, Shawnee Chief Cornstalk attacked the Virginia militia, hoping to halt their advance into the Ohio Country. This became known as the Battle of Point Pleasant. The battle raged on until Cornstalk finally retreated. The Virginians, along with a second force led by Lord Dunmore, the Royal Governor of Virginia, then marched into the Ohio Country. Cornstalk had no choice but to agree to a treaty, ending the war. Many men on both sides lost their lives in the battle, including Richard Trotter.

For Anne this could have meant years of sadness as a widow, but Anne would have none of that. Anne, upon learning of her husband’s death, and determined to seek revenge, left her young son in the care of neighbors, dressed in the clothing of a frontiersman, and set out to avenge her loss. A woman alone going out to kill the Indians seemed like an insane move to make, and most people probably thought she would be dead in a matter of days…but they didn’t know Anne. She became known as “Mad Anne” from that time forward….to whites and Indians alike. In the beginning, Anne rode from one recruiting station to another, asking them 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.

People from Staunton, Virginia, to what is now Charleston, West Virginia, and Gallipolis, Ohio, knew Anne, mostly due to the unusual sight she presented. She usually wore buckskin leggings, petticoats, heavy brogan shoes, a man’s coat and hat, a hunting knife in a belt around her waist, and a rifle slung over her shoulder…everything she needed to be in the pioneer spirit in the late 1700s. Although Mad Anne mostly 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. It seemed that there was no job she wouldn’t take, including traveling as a courier on horseback between Forts Savannah and Randolph, a distance of almost 160 miles. Her fearless personality made her well known and respected by the settlers along the route. Mad Anne was even respected, or maybe feared is a better word, by the Shawnee Indians. On her rides Bailey often came across a particular group of Shawnee Indians. They often chased her, then on one such encounter, she had had enough. Just when she was about to be caught, she jumped off her horse and hid in a log. Strangely, the Shawnee looked everywhere for her and even stopped to rest on the log, but they could not find her. Finally, they gave up and stole her horse. She waited a while after they left, and then came out of the log. She waited until nightfall, then crept into their camp and retrieved her horse…a bold move, but nothing like the next move she made. Once she was far enough away, she started screaming and shrieking at the top of her lungs. Now waking up to that would be shocking enough, but this woman was acting totally crazy, and the Shawnee thought she was possessed and therefore could not be injured by a bullet or arrow. After that display, the Shawnee saw her often, but the kept far away from her, because they were totally afraid of her. With that assurance backing her, Mad Anne knew that she was relatively safe living in the woods.

Anne met John Bailey, a member of a legendary group of frontier scouts called the Rangers, after several years living on her own. The Rangers were defending the Roanoke and Catawba settlements from Indian attacks. He was rather smitten with Mad Anne’s rough ways, and they were married November 3, 1785. In 1787, along the Kanawha River at the mouth of the Elk River, a blockhouse was built. The block house would later become Fort Lee in honor of Virginia’s Governor Henry Lee. Fort Lee was where John Bailey was assigned to duty, taking with him his now famous, gun-toting, hard-riding bride.

In 1788, John Bailey was transferred to Fort Clendenin, which was a more active area of 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, she singlehandedly saved Fort Lee from certain destruction by hostile Indians with a three-day, 200–mile round trip to replenish their supply of gunpowder. She rode for hours, finally reaching Fort Savannah at Lewisburg, where the gunpowder was quickly packed aboard her horse and one additional mount, before she reversed her direction and galloped full speed back to Fort Lee.

After she returned, the siege was ended, the attackers were defeated. For her bravery Anne was given the horse that had carried her away and brought her safely back. The animal was said to have been a beautiful black, sporting white feet and a blazed face. She dubbed him Liverpool, in honor of her birthplace. Anne Bailey was forty-nine years old when she made this famous ride. Anne became a legend among the other settlers, and she was always welcome in their homes. John Bailey died in 1802, and Anne decided that she no longer wanted to live in a house, so she lived in the wilderness for over 20 years. She visited friends in town occasionally, but usually slept outside. Her favorite place was a cave near Thirteen Mile Creek.

A widow for the second time, and in her late fifties, Anne later went to live with her son, but her love for riding and of the wilderness had not ceased. For many years afterwards she could be seen riding from Point Pleasant to Lewisburg and Staunton, carrying mail and as an express messenger. Bailey continued working as a messenger, bringing supplies for the settlers throughout the area. She finally retired in 1817 after making one last trip to Charleston at age 75. In 1818 Anne moved with her son and his family to his new farm in Gallia County, Ohio. Instead of asking her to stay with his family, her son, who had apparently never felt any ill-will toward his mother who was often not around, built her a cabin nearby so she would still feel independent. Bailey continued working as a messenger, bringing supplies for the settlers throughout the area. Anne Hennis Trotter Bailey died at Gallipolis, Ohio, November 22, 1825, at the age of 83. She was buried in the Trotter Graveyard near her son’s home, and her remains rested there for seventy-six years. On October 10, 1901, her remains were re-interred in Monument Park in Point Pleasant, under the auspices of the Colonel Charles Lewis, Jr. Chapter of the D. A. R.