Ann Hennis Trotter Bailey (1742-1825)


Ann Hennis Trotter Bailey is known as “Mad Ann” for her acts of bravery and heroism that were considered to be somewhat eccentric for a woman of her time.  She worked as a scout and messenger during the Revolutionary War. Bailey was most known for her 100 mile ride from Fort Clendenin to Fort Savannah in order to bring back much needed gun powder.

Ann Hennis Trotter Bailey was born in Liverpool England in 1742.  She was formally educated and learned to read and write.  Both of her parents had died by the time she turned 18.  Bailey was poor and had a hard time earning enough money to survive.  When she was 19 she sailed to America.  Some say she went to stay with relatives but other sources say that she became an indentured servant in order to pay for her trip to America. 

In 1765, Bailey married Richard Trotter and moved to Staunton, VA in the Kanawha Valley area.  As more and more people moved West, fights broke out between the settlers and the Native Americans that already lived in the area.  The Governor of Virginia organized border militia to help calm the area.  Trotter joined this militia and participated in the battle at Point Pleasant that took place October 10, 1774.  This battle is known by some as the first battle of the American Revolution.  The battle prevented these Native Americans from becoming allies to the British.  Although the Settlers won the battle, there were massive casualties on both sides.  Richard Trotter was killed. 

After learning her husband had died, something in Bailey changed and she swore to avenge her husband’s death.  Some say this is the point when she turned “Mad”.  Bailey began wearing men’s clothing and taught herself how to shoot a gun.  She volunteered her services as a scout and messenger and was adamant about doing anything she could for America’s Revolution.  Bailey felt a strong duty to her country and that her participation was important. 

Bailey left her 7 year old son with a neighbor and rode up and down the border encouraging men to volunteer their services to join the militia in order to keep the women and children of the border safe.  Bailey often traveled between Fort Savannah and Fort Randolph carrying messages back and forth.  The distance between the two Forts was almost 160 miles.  She knew all the paths and was highly valued.  Bailey was well known and respected by all of the settlers along the route. 

On her rides Bailey often came across a group of Shawnee Indian’s.  In one such encounter, Bailey was being chased by them and about to be caught when she jumped off her horse and hid in a log.  Though they looked everywhere for her and even stopped to rest on the log they couldn’t find her.  They gave up and stole her horse.  After they left, Bailey came out of the log and during the night snuck into their camp and stole her horse back.  When she was far enough away she began to scream at the top of her lungs. The Shawnee Indians thought she was possessed and could not be touched by a bullet or arrow.  After this event they saw her often, but they feared her and only watched her from afar.  Therefore, Bailey was relatively safe living in the woods and did not need to fear being attacked by Indians. 

After several years living on her own Ann Bailey met John Bailey, who seemed to enjoy “Mad” Ann Bailey’s rough ways.  They were married in 1785.  He was a “Ranger”, one of the most legendary groups of frontier scouts.  In 1788, John Bailey began duty at Ft. Clendenin where there was more conflict between the settlers and Native Americans.  Ann Bailey began working for the settlers as well and rode around warning them of impending attacks. 

In 1791 Native Americans were planning an attack on the Fort.  The militia discovered that they did not have enough gun powder to successfully fight the Native Americans.  The ride was over 100 miles and very dangerous.  When the Colonel asked for a volunteer none of the men offered so Bailey did.  It is said that she rode the whole way without stopping to sleep or rest.  When she reached Fort Savannah they gave her the powder and an extra horse. They also offered to get her an escort but she refused.  Bailey returned a hero and was rewarded with whiskey and the horse she had rode.  Later, a song was written about her famous ride.  Bailey became a legend among the other settlers and she was always welcome in their homes. 

When John Bailey died in 1802, she gave up her home and lived in the wilderness for over 20 years.  She visited friends occasionally but often slept outside.  A cave near 13 mile creek was said to be her favorite place to sleep. 

Another story that has not been verified is that Bailey brought the first geese to Kanawha Valley.  She was contracted by Colonel William Clendenin to bring him 20 geese, no more no less or he wouldn’t pay.  On the way back one died so she put it in a bag and continued on.  When he said he wouldn’t pay because there were only 19 she threw the dead goose on the ground and said, “There’s your 20” (1)

Bailey continued to messenger supplies for settlers from all over.  She made her last trip to Charleston in 1817, at age 75.  In 1818, she reluctantly moved with her son to Gallia County in Ohio.  Instead of asking her to stay with his family, her son built her a cabin close to his house so that she would still feel independent.   

In 1823, Ann Bailey was interviewed by Anne Royall, a local reporter.  When speaking of her adventures and bravery she said, “I always carried an ax and auger, and 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” (2)

She died on November 22, 1825 and was buried in Gallia county however, later her remains were moved to Point Pleasant. 

There are two other women by the name of Ann Bailey who were also gallant enough to have their names remembered for their participation in the Revolutionary War.  Anna Warner Bailey is known for her efforts during the Battle at Grotton Heights in 1781.  After the battle was over she walked three miles in search for her uncle.  When she found him he was badly wounded and requested to see his wife and daughter.  Anna Bailey ran home, caught the horse, saddled it, and brought his wife and daughter back to him.  Bailey then proceeded to attend to all the other wounded soldiers.  When she found out that there was a flannel shortage she visited all of the homes in the area and collected the flannel needed to make cartridges for muzzle loader guns.  She also donated her own flannel petticoat. 

Ann (or Nancy) Bailey tried to enlist into the militia as Samuel Gay on February 14, 1777.  Within three weeks Bailey attained the rank of corporal.  After three weeks she deserted, most likely because her identity was discovered.  A warrant was placed for her arrest and she was discovered as a female.  Bailey was fined and sentenced to two years in prison for dressing as a man. 

Additional Resources:



  • Resmond, Shirley Raye.  Patriots in Petticoats: Heroines of the American Revolution.  (New York:  Random House Children’s Books, 2004).
  • Life and times of Ann Bailey: Pioneer Heroine of the Great Kanawha Valley by: Virgil A. Lew



(1) Cammarata, Kathy.  “Won’t You Come Home, Anne Bailey?  A fearless pioneer woman risked her life as a Revolutionary scout”.  Southeast Ohio Magazine. Spring 2001. 21 June 2006.
(2) Cammarata,
Image from: Hollis, Suzanne. “Anne Bailey, American Patriot.” The American Revolution. (21 June 2006). 


Biography researched and written by NWHM Intern of Summer 2006 Albrey Diece