Many people believe an old legend that Anne Bailey once rode through dangerous territory to bring gunpowder to defend Fort Lee in present-day Charleston from an Indian attack in 1790. However, there is no proof that either the attack or her ride ever happened. Still, she was a brave and tough woman who helped protect frontier settlements.

Born in Liverpool, England, she moved to Virginia and was living in Staunton by 1761. In 1765, she married Richard Trotter. After he was killed in the Battle of Point Pleasant in 1774, she promised to fight for revenge. She taught herself to shoot and became a scout. For 11 years, she traveled through the wild lands of western Virginia, carrying messages between forts.

In 1785, she married John Bailey, a soldier from Greenbrier County, but continued her scouting work.

Whether or not the Fort Lee story is true, Anne Bailey played an important role in helping frontier communities. After peace came in 1795, she carried mail between towns and helped move animals across the state.

She is buried at Point Pleasant, where a monument honors her courage and service.