Bailey earned the nickname "Mad Anne" for her exploits, which made her a bit of an eccentric for a woman of the time. She was born in Liverpool, England in 1742. She was an educated woman, but a poor one. Anne lost both her parents when she was 18. At the age of 19, she sailed for America in the hopes of a better life. Some sources suggest she worked as an indentured servant to pay for her trip.
In 1765, Anne married Richard Trotter and her life seemed to take a turn for the better. The couple had one son, William, and lived in the Kanawa Valley in Staunton, VA. Unfortunately, there were a lot of settlers moving out west and it was causing a lot of tension with local Native Americans. Numerous fights were breaking out, which led to the governor of Virginia to organize a militia to keep the peace (because if there's one way to ensure peace, it's organizing a bunch of angry settlers into a militia). Anne's husband joined the militia and took part in the battle of Point Pleasant. This battle prevented the Native Americans from allying with the British during the American Revolution. Both sides suffered heavy losses in this battle and Richard Trotter was one of the ones who fell.
Anne Trotter was pissed. The "swearing bloody vengeance" kind of pissed. She dropped off her seven year old son with some neighbors (she had no relatives) and promptly took up arms. I like to think she said something like, "I'm going out to spill some blood. Look after my boy while I'm gone."
Baily began wearing men's clothes and taught herself how to shoot, ride a horse, hunt, and soon becoming a very adept scout. She volunteered her services as a scout and messenger. She was dedicated to the colonists cause and wanted to make sure they won the war. She drummed up support for Washington's army, often riding from station to station along the Potomac recruiting volunteers. Anne would carry messages between Fort Randolph and Savannah, a distance of 160 miles. She knew the paths like the back of her hand and the settlers along her route highly respected her.
In 1785, Anne married John Bailey, a member of the Rangers (frontier scouts), who loved her somewhat wild ways. She was known to enjoy drinking, cursing, and telling stories, behaviors that were anything but lady-like. The two were a good match for each other. In 1788, John began duty at Ft. Clendenine. Again, the settlers and local Native Americans were clashing and the situation was becoming volatile (probably in no small part to the settlers once again trying to push the Native Americans off their lands). Anne still worked as a courier and warned settlers of impending attacks.
In 1791, the militia learned the Native Americans were planning an attack. Worse, they were severely low on gunpowder. So low, they would not be able to hold off the attack. Someone had to ride 100 miles to Lewisberg to get more gunpowder, a suicide mission. The colonel in charge asked for volunteers to ride over a hundred miles through hostile territory and very likely to his death. The men remained quiet, likely looking at their shoes, which probably became inexplicably fascinating. Anne, realizing none of the men were going to volunteer, raised her hand and stated that she would do it (probably after insulting the men).
Anne hopped up on her horse and raced off into the wild. Legend says she rode day and night, up the Kanawha Valley to the Greenbriar Mountains. Once she reached her destination, Anne retrieved the gunpowder and a horse to carry it. She was offered an escort, but turned it down (probably saying, "fuck that. He'll just slow me down!"). She returned to Fort Clenendine and the soldiers were able to fight off the attack the morning after she returned (hopefully while she took some much deserved rest). Anne's impressive ride was eventually immortalized in a poem by Charles Robb (Anne Bailey's Ride). It's a somewhat embellished version of the ride and the description of Anne is entirely wrong.
John Bailey died in 1802. Anne Bailey went on to be a trader and storyteller. She often slept outside, having no desire to remain indoors for long stretches of time. She continued to act as a messenger for settlers, bringing supplies they needed. She made her last trip in 1817, at the age of 75. After that, she went to live with her son. William, knowing his mother valued her independence above all else, had a cabin constructed next to his home where she lived out her days, often entertaining guests with vivid tales of her adventures.
Anne Bailey never feared death. She often bragged that she could chop and shoot as well as any man. Coming from a humble background, Anne lived the life she chose and on her own terms. To me, that is incredibly impressive.
Image found here
Howlett, Charles F. "Anne Trotter Bailey." Women and War: A Historical Encyclopedia from Antiquity to the Present. Santa Barbara: ABC-CLIO, 2006. 46-47. Google Books. ABC-CLIO. Web. 11 July 2014.
"Anne Bailey." Wikipedia. Wikimedia Foundation, 07 May 2014. Web. 11 July 2014.
Diece, Albrey. "National Women's History Museum." Education & Resources. National Women's History Museum, 2006. Web. 11 July 2014.
Next week: the force of nature that was Josephine Baker