"Mad Ann" Bailey

A pic a friend and I took of the grave of Ann Bailey when we visited Point Pleasant in 2022

“Mad Ann” Bailey was a famous frontierswoman. History.com names her one of the 7 gutsiest women on the American frontier, in a March 2018 article. 

 I went to Ann Bailey Elementary, where I think I was misinformed about who Ann Bailey really was, or maybe after all these years, I just don’t fully remember what I was taught. In any event I was surprised to re-learn about Ann Baily in recent years. 

Ann Hennis came from Liverpool, England around 1761 to Virginia. She was an educated woman. She married her first husband, Richard Trotter, in Virginia. Richard was a Shenandoa Valley settler. He also participated in and survived General Edward Braddock’s disastrous expedition of 1755 (a major event in the French and Indian war). Richard was killed in Lord Dunmore’s war AKA The Battle of Point Pleasant. I covered Lord Dunmore’s war in detail in my book, Celebrating 161 Years of West Virginia, if you want to read more on that. Now, after Richard’s death in 1774, Ann started to act a little different. She started to dress like a man and took up a rifle and a tomahawk. This type of thing earned her the nicknames “Mad Ann” Or “White Squaw from the Kanawha”. 

With the new look and nicknames, Ann also became a frontier scout, spy and Indian fighter. She was seeking revenge on the natives who killed her husband. She would take messages back and forth between Point Pleasant and Lewisburg- a nearly 200-mile horseback ride. On her rides, she would run into a group of Shawnee Indians. On one ride, she was chased by them, and she knew she would he caught, so she jumped off her horse and hid in a hollow log. The Indians looked for her for a long time and even sat to rest on the log which she was in. They eventually gave up and just stole her horse. That night, Anne snuck into their camp and stole her horse back, screaming as she rode away. After seeing this, the Indians thought she was immortal and didn’t bother her anymore 

 She married her second husband, John Bailey, in 1785 and relocated to Clendenin’s Settlement AKA Fort Lee (present day Charleston). This is where she made her most famous ride in 1791.  Soldiers at Fort Lee had got word that the Native Americans were planning to attack. Big problem because they were very low on gun powder, and they would need somebody to make the 100-mile trip to Lewisburg. No problem for Ann, so she volunteered. This ride would go down in history and there is a famous poem that was written about it too. She was given a black horse as a reward for her service. She named the horse ‘Liverpool’ in honor of her home. Her second husband died in 1802, and Anne is said to have spent the next twenty years living in the woods. She eventually went to live with her son in Ohio, he was her son from her first marriage. She died there in Ohio at the age of 83 on November 22 of 1825. She was buried in the Trotter graveyard and was there for 76 years but was moved to Point Pleasant on October 10th, 1901, by a chapter of the daughters of the Revolution, not far from where her first husband was killed. 

 

When asked about her bravery by a local reporter in 1823, Anne had this to say “I always carried an ax and an auger, I could chop as well as any man. I trusted in the almighty. I knew I could only be killed once, and I had to die sometime” 

A local legend in Charleston is that on a quiet night by the river on the boulevard, you can still hear the phantom hoofbeats of Liverpool (her horse) 

Sources 

Women in the Revolution-Ann Bailey, womenhistoryblog.com 

7 of the gutsiest women on the American frontier, Brynn Holland, March 8th, 2018, History.com 

Ann Bailey, Brittanica.com 

Braddock’s defeat, 1775: French and Indian war, Chuck Lyons, February 7, 2017, historynet.net