Bailey was said to have been born Anne Hennis in Liverpool, England, and to have been named for Queen Anne, who was on the throne of England when Bailey’s father, whose name is not recorded, fought at the Battle of Blenheim. When she was about nineteen years old she immigrated to Virginia and settled in Staunton, where in 1765 she married Richard Trotter, a veteran of the French and Indian War who had fought under General Edward Braddock and Colonel George Washington in 1755 and who was later killed at the Battle of Point Pleasant on October 10, 1774. They had one son.
Tu-Endie-Wei State Park, West Virginia
Documented facts about her life during the decade following Trotter’s death are scarce, and many legends, some of them very improbable, have developed to fill the void. Several legends persistent enough that they may contain some truth have her leaving her son with friends, dressing in men’s clothing, and living a rough frontier life. She may have reported on movements of Native Americans during and after the Revolutionary War when frontier settlers often feared surprise raids. According to legends that developed about those years, she once killed two Native Americans with one well-aimed rifle shot, slept in holes under rocks or in hollow logs, and avoided freezing to death one winter night because her horse breathed warm air into a hollow log. Other legends had her roaming the frontier and killing Native Americans in many places to avenge the death of Richard Trotter, giving rise later to the sobriquet Mad Anne, or Mad Anne Bailey, her name after she married John Bailey in Greenbrier County on November 3, 1785.
The Baileys lived for nine years at Fort Lee at the site of present-day Charleston, West Virginia. The most famous Anne Bailey legend begins at Fort Lee late in the 1780s or perhaps as late as 1791. A Shawnee party was seen near the fort, and the inhabitants were thrown into panic when they discovered that the fort was out of gunpowder. Braver or more reckless than the men, Anne Bailey mounted her horse and rode all the way to Lewisburg, picked up a supply of powder, and returned to the fort with angry Native Americans or hungry wolves or both in hot pursuit, just in the nick of time to save all of the settlers. This legend, which did not appear in print until the 1860s, and the other tales have subsequently appeared in many different versions, some of them masquerading as history, many of them transparently fictional, some in song, and one of them in a long poem composed in 1861, but none of them with substantiating documentation.
She was well known in western Virginia, though, probably because some of the legends had some truth in them. One of the first references to carry Bailey’s name far beyond her western Virginia home was Anne Newport Royall’s Sketches of History, Life, and Manners, in the United States (1826). Royall introduced “the celebrated heroine, Ann Bailey” to her readers and described her as “a Welch woman,” short and stout in her old age, fond of strong drink, and speaking with a pronounced accent. Royall did not include any of the taller tales about Bailey, but she did state that during the Revolutionary War Bailey “would shoulder her rifle, hang her shot-pouch over her shoulder, and lead a horse laden with ammunition to the army, two hundred miles distant, when not a man could be found to undertake the perilous task.” That brief account may have referred to her salvation of Fort Lee, but it is also possible that the more colorful and dramatic tale of her rescue of Fort Lee arose out of that brief account.
John Bailey died not long before November 1794. Anne Hennis Trotter Bailey continued to reside in, or wander up and down, the Kanawha River Valley for several years until her son, William Trotter, forced the reluctant old woman to move to his farm in Gallia County, Ohio, where she lived alone by choice in a crude log cabin on his property. She died there on November 22, 1825, asleep with her grandchildren before her own fireplace. On October 10, 1901, her remains were reinterred in Tu-Endie-Wei Park in Point Pleasant, West Virginia, near the spot where her first husband had been killed fighting the Shawnee.