The Wild West of Yester-Year

Anne Bailey

By Rachel Kovaciny

 

Today, the idea of Virginia having ever been part of the American frontier seems silly. When we think about the history of our country, Virginia definitely springs to mind, but as an important setting for major Revolutionary War and Civil War battles. It’s a state we might associate with colonists and statesmen and great military generals. But frontiersmen and frontierswomen? Not really.

 

However, during the early days of our country, much of Virginia remained a frontier. When American colonists talked about moving to The West to build their homes where the countryside was wild and free, they meant what is now western Virginia and West Virginia. Although I wouldn’t exactly call it the Wild West, it’s still part of the history of our nation’s westward expansion. And it was still plenty wild in the mid-1700s. In fact, it was so wild, no one seems to have raised any eyebrows at a woman named Anne Bailey joining the militia to replace her deceased husband and serving as a scout and courier for the military. Or, if they did, they didn’t raise them very high, at least not in her presence.

 

Born Anne Hennis in Liverpool, England, Anne received a formal education, an oddity for girls at the time. After her parents died in her late teens, Anne sailed westward to see what the American colonies were like. She settled with relatives near Staunton, Virginia, in the Shenandoah Valley. There, Anne married Richard Trotter in 1765, ten years before the American Revolution.

 

Richard Trotter was an experienced and respected frontiersman and former soldier who had served under General George Washington during the French and Indian War. Together, they had a son named William. The Staunton area was on the frontier, with English settlers moving out into lands inhabited by native tribes such as the Shawnee. Skirmishes between the two groups led to a militia being formed to protect the settlers, a militia Richard Trotter joined. In 1774, he died in the Battle of Point Pleasant against the Shawnee.

 

Anne entrusted their young son to a neighboring friend and took her husband’s place in the militia. She did not disguise herself as a man, but simply stepped into her husband’s spot and performed his military duties. She wore a skirt and petticoats, with buckskin leggings underneath them, and a man’s boots, coat, and hat. Equipped with a rifle and a hunting knife, Anne worked as a courier by delivering messages for the Virginia militia during the American Revolution, and scouted for the military. And she served as a recruiter for the revolutionary cause, stopping at farms and taverns along her route to encourage men to join the new American Army.

 

After the Revolution, Anne remarried to another scout, John Bailey, and they moved to a far-flung frontier settlement called Clendenin’s Settlement (now Charleston, West Virginia). This settlement had grown up around Fort Lee, a military outpost that Anne famously saved. During the Northwest Indian War in the early 1790s, a large party of Shawnee warriors besieged Fort Lee. The soldiers and settlers sheltering in the fort ran low on gunpowder and were in danger of having to surrender. Legends have clouded the facts, but Anne took it upon herself to ride over a hundred miles alone through hostile wilderness to Fort Savannah, the closest military station. There, she convinced the commander to give her the gunpowder needed at Fort Lee and then rode back with it, evading capture by the Shawnee all the way.

 

This heroic action saved the fort and its inhabitants, and it earned Anne Bailey folk hero status immediately. Legends and myths grew up around her, such as a tale about her military scouting days in which the Shawnee gave her the nickname “Mad Anne.” The legend says some native warriors had nearly caught her, but she turned her horse loose to let her pursuers capture it, hid inside a hollow log to escape them, then sneaked into their camp to get her horse once night fell. As she rode her horse away from them, she let loose with a series of triumphant yells and whoops that made the Shawnee warriors think she had either gone mad or that her ghost came to reclaim her horse. After Anne’s second husband died in 1794, she moved in with her son William and his family, and lived with them on their farm in the new frontier region of Ohio. Anne Bailey died peacefully on her son’s homestead in 1825, at age 83.

 

We also tend not to think of Ohio as the frontier, but once Virginia got more or less civilized, pioneers pushed farther west into Ohio, and eventually into what we now think of as the American West. ♦