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What Happens When a Patriot Woman Goes Off the Deep-End? A Legend is Born!

by Heather Frey Blanton


Re-enactment. She actually wore a wide-brimmed hat with a feather stuck in it. Perhaps to look more like a man from a distance?

Re-enactment. She actually wore a wide-brimmed hat with a feather stuck in it. Perhaps to look more like a man from a distance?


Ann Hennis Trotter Bailey. Anyone even remotely familiar with the history of the Kanawha Valley of Virginia has heard the stories of “Mad” Ann. Perhaps she was crazy as a bed bug, but Indians feared her, settlers loved her, and America owes her a debt of gratitude.

Born in England, Ann was an orphan before the age of 18. She worked hard to make a living but life was hard in those days for an unmarried girl trying to make a decent living. The Colonies, though, beckoned to her, and she made her way to America sometime in the early 1760’s. We know she married Richard Trotter in 1765 and the two moved to the frontier of Virginia, a wild place boiling over with tension between the Native Americans and eager settlers. The couple built their lives among the tall pines, working a successful homestead that provided for all their needs.

The Revolutionary War came calling, though, and in 1774, Richard was killed in a battle with Native Americans who were attempting to side with England. By all accounts, Richard’s death affected Ann deeply and she swore vengeance on the Indian and the English alike. England’s attempt to squash her dreams of independence ignited a fury in Ann. The loss of her husband, though, fueled her hate like a nuclear reactor.

As skilled at living in the woods as any frontiersman, Ann put on her husband’s clothes, especially his buckskin breeches, brushed up on her shooting skills, and left her seven-year-old son with a neighbor. Fanatical about the war, she rode all through the valley and the border area, urging men to join the fight to save their liberties and protect their families. She carried messages for the Colonial Army and supplies for the settlers. Ann repeatedly made the ride from Fort Savannah to Fort Randolph, a journey of 160 miles, alone and with only one horse.

And apparently she was very fond of her horse.

On one fateful journey, a group of Shawnee Indians took off after Ann. Galloping through the woods at a breakneck pace, she realized she couldn’t outrun the warriors. Always thinking, she leaped from the horse and hid in a hollow log. The Indians scrambled all over the area but couldn’t find her, so they settled for stealing her horse. Ann bided her time and then, in the wee hours of the morning, slipped silently into the Indian encampment. She procured her mount and made her escape. Oh, but she couldn’t go without a victory dance. Some ways from the camp, she rose in the saddle and started yelling obscenities at the Indians. In fact, she screamed and hollered curses at the warriors at the top of her lungs.

She must have been a site to behold because the Shawnee warriors didn’t follow her. In fact, convinced she was utterly mad, they never accosted her again. Ann Bailey lived in the woods for several years and then, amazingly, in my opinion, re-married. Husband number two was a good fit, though. John Bailey was a woodsman himself and a member of the legendary frontier scouts, the Rangers. Just as rugged as she, he did, however, coax Ann back to living indoors.

The two shared many adventures together, fought in some hot battles, and gave it all to build America. Now, that’s the kind of “mad” American girl I’m down with.

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