Ann Bailey, one of the most picturesque characters in American border history, was known as “Mad Ann,” because of her waspish temper. Her maiden name was Dennis, and she was a native of Liverpool, England. Like many other persons of her time, she came to Virginia as an indentured servant, and paid the cost of her passage across the Atlantic by being bound into servitude for several years. During this period in her life she was at Staunton.
At the age of twenty-three she married James Trotter, who was killed nine years later in the battle of Point Pleasant. William Trotter, her only child, was born near the present village of Barber in 1767.
After Trotter was killed the widow resolved to avenge his death. She left her boy with Mrs. Moses Mann, put on masculine apparel, and became a hunter and scout. She rode a black horse that she called “Pool,” an abbreviation of Liverpool. Her other horse she named “Jennie Mann.”
It is said of Ann Bailey that she put more than one Indian out of the way. On one occasion her lead horse was stolen from her.
Source: A Centennial History of Alleghany County Virginia.
This chapter would not be complete without some mention of that eccentric and masculine woman, known to American border history as Mad Ann Bailey. She was given this name because of her irascible Welsh temper. Her maiden name was Dennis, and she was a native of Liverpool. She came to Staunton at the age of 13, and ten years later wedded James Trotter, who was killed at Point Pleasant. The pair had a son named William, who was born in 1767.
Ann Bailey left her child with Mrs. Moses Mann, a near neighbor, put on masculine apparel, and for several years was a hunter and scout. One of her reasons for adopting such an unfeminine career was to avenge the death of her husband. According to tradition she took more than one scalp.
Her 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.
For a year or so, she lived in a hut on Mad Ann’s Ridge, on the south side of Falling Spring Run. On one occasion her black horse went on to Mann’s without his rider. A party from the stockade went out to follow the trail, and located Mad Ann by airholes in the snow. She had failed asleep, either from liquor or drowsiness.
According to Ann Royall, who knew her in her old age, she could both drink and swear.
Source: Annals of Bath County Virginia
More recent references spell her name as Anne instead of Ann. The Anne Bailey Elementary School in St. Albans, West Virginia, is named for “Mad Anne” Bailey as is the Daughters of the American Revolution chapter in Charleston, West Virginia and a lookout tower in Watoga State Park.
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