Inspiring Women of History: "Mad" Anne Bailey

By Kristi Waterworth

We all know the story of Paul Revere, who rode through New England screaming and waking a lot of folks up late at night because some guys in red coats were coming.  A story a lot fewer of us know is that of Anne Bailey, a frontier scout who served proudly in both the American Revolutionary War and the Northwest Indian War.  Anne was English, from Liverpool, same as my ancestors, and was orphaned by age 18.  

Since she had no one else and no where to be, she set sail for America in the late 1750s or early 1760s.  It's unclear if she paid her own way or if she entered into indentured servitude in exchange for passage, but if she did, the term was very short.  By 1765, she was married to an American named Richard Trotter and promptly took up residence in the Kanawha Valley area of Virginia.

The valley was turbulent, though, experiencing a great deal of violence between settlers and Native Americans (who were, by all rights, there first).  The governor raised a militia to help patrol the border and protect these settlers, Mr. Trotter enlisted gladly.  Unfortunately, he was killed at the Battle of Point Pleasant on October 10, 1774 – this battle is understood by some historians to be the first of the American Revolution.

Something in Anne snapped when she learned of her husband's death – she donned men's clothing (both illegal and scandalous at the time), learned to shoot a rifle and threw in with the Patriots.  Throughout the war, she served as a scout and messenger between Fort Savannah and Fort Randolph, a distance of about 160 miles.  During her travels, she recruited men for the militia from the towns she passed and was an adamant supporter of the American colonists in every way.

After America won its freedom, Anne continued to serve as a messenger and scout in the area until she married John Bailey, an elite frontier ranger.  Together they moved to Fort Lee, near Charleston, West Virginia, and continued to carry messages, scout and protect settlers from Native American attacks.  This is where a rough, unusual women turned legendary.  

In 1791, the fort received word that a party of Native Americans was headed right for them and discovered they were short on gun powder.  With the Natives bearing down on them, the settlers were desperate, but when the militia asked for a volunteer to ride the 100 miles to Fort Savannah for emergency supplies, none of the men stepped forward.  But no worries, because Anne took the job.  

The road was perilous, running through unsettled wilderness, but Anne wasn't afraid – someone had to save the fort or everyone inside might be killed.  She mounted a horse and rode the 100 miles without stopping to sleep or eat; she lingered at Fort Savannah only long enough to change horses and load her freight.  Anne rode back to the fort with the same gusto she left it, refusing even an escort from Fort Savannah.  Her quick return (and subsequent saving of the fort) earned her a hero's welcome, whiskey and the horse she rode back in on.  

After that it was business as usual for Anne and John.  When he died in 1802, Anne moved out to the wilderness, sleeping outdoors or in caves, according to legend.  She continued to carry messages until 1817, retiring at age 75.  Her son built a cabin on his property for his mother; she died on the property in 1825.

Kristi Waterworth is a freelance journalist based in Springfield, Missouri with a wide range of interests; her work frequently appears on the web and in print. Waterworth developed a long love affair with the Westerning Experience while studying American history in college. Despite the lies, intrigue and mythology intertwined with fact, the American West was a place and time like no other – the extreme adventure required an extreme response. She now seamlessly integrates her journalism skill with her history background at an irregularly updated site called Fifteen Minutes. You can also catch up with her on Facebook and, of course, here on I Feel Delicious.