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Haunted Appalachia: On the Frontier Road with Mad Ann Bailey

By Staff | Aug 29, 2018

Her name was “Mad Ann” and the Native Indians feared her and for good cause. Many frontier folk thought her crazed and a few called her brave but in any case, she certainly left her mark on frontier history throughout the Ohio and Western Virginia wildlands.

I have stood at her grave along the Ohio River on many occasions. During last year’s infamous Mothman Festival in Point Pleasant, I gazed at her notso-favorable portrait, which is etched into her granite stone and I wondered, “How did a woman like Ann manage to survive famine, communicable diseases, Indian attacks and the hard living common to the pioneers along the Ohio River? She musta been one tough ol’ broad.”

History tells us that Ann was a famous storyteller. She was a frontier scout and messenger who served in the fight of the American Revolutionary War and the Northwest Indian War. In history books, you may recall that her solo 100-mile horseback ride in search of a desperately needed powder supply for the endangered Clendenin’s Settlement (present day Charleston) gained her the nickname as the “Heroine of the Kanawha Valley”. Ann Hennis Trotter Bailey became known as “Mad Ann” for her acts of bravery that were considered to be somewhat eccentric for a woman of that era and at age 50 to boot!

Ann came from modest means and was born in the year 1742 in Liverpool, England. She traveled to America and settled outside of Staunton, Virginia where she soon married Richard Trotter and had a son that they named William. On Oct. 10, 1774, her life was changed when her beloved husband was killed at the battle of Point Pleasant. She was unable to take care of her son and gave him up to the care of a neighboring family. Life can throw us a curve ball and Ann made the best of it.

After the death of her husband, she changed. She swore to avenge her husband’s death and some say this is the point when she turned mad. Ann began wearing men’s clothing and taught herself how to shoot a gun – and very well at that! On her rides, Ann often came across a group of wandering Shawnee. In one such encounter, she was being chased by them and about to be caught when she jumped off her horse and hid in a log lying on the forest floor. Though they looked everywhere for her and even stopped to rest on the log, they could not find Ann. They gave up eventually and took her abandoned horse. After they left, Ann came out of the log and during the night, she snuck into their camp and stole her horse back. When she was far enough away she began to scream and shout at the top of her lungs. The Shawnee thought she was possessed and “teched in the head” and with that thought, they believed she could not be harmed by a bullet or arrow. After this event, they saw her often but the warriors feared her and would only watch her from afar.

Love came again for Ann and after several years living on her own, she met John Bailey, who seemed to enjoy “Mad” Ann’s rough ways. They were married in 1785. When John died in 1802, she gave up her home and lived in the wilderness for more than 20 years. She visited friends occasionally but often slept outside as this was what she was accustomed to. Her hard frontier ways must have stuck with her. She died suddenly on Nov. 22, 1825, while sleeping with her two little grandchildren.

As I stood at her grave near the Ohio River on that beautiful September day and thought of her trials and tribulations, I gave her black shiny headstone a touch and I told her goodbye. She was one soul who did not make many history books but her story truly resonated with me. Quiet woman rarely make history. I like to think that Ann is continuing her eternal ride on a black horse named Liverpool on the rutted frontier roads in the afterlife.

Sherri Brake is a paranormal researcher, author and Haunted Heartland Tour owner. You may email her at SherriBrake@gmail.com or visit her website at www.HauntedHistory.net