He survived multiple gauntlets and ritual torture applied to war captives, and was said to be rescued by Simon Girty.

In 1771, at the age of 16, thinking he had killed William Leachman in a jealous rage (the fight began over the love of a girl named Ellen Cummins), Kenton fled into the wilderness of what are now West Virginia, Kentucky, and Ohio.

In 1774, in a conflict later labeled Lord Dunmore's War, Kenton served as a scout for the European settlers against the Shawnee Indians in what is now West Virginia and Kentucky.

Girty suggested the Shawnee take Kenton to a trading post at Upper Sandusky, where the British paid off their Indian allies.

"[2] Kenton served as scout on the 1778 George Rogers Clark expedition to capture Fort Sackville during the American Revolution.

Kenton started exploring the area of the Mad River Valley of Ohio and making claims as early as 1788.

Independence did not mean an end to warfare; in 1793–94, Kenton fought in the Northwest Indian War with "Mad" Anthony Wayne.

In April 1799, Kenton and his associate, Colonel William Ward, led a group of families from Mason County, Kentucky to an area between present-day Springfield and Urbana, Ohio.

Later, his widow Elizabeth Jarboe Kenton and a number of their children moved to northwestern Indiana, to an area straddling Jasper, White, and Pulaski counties.

A statue honoring him was erected in Covington, Kentucky's Riverside Drive Historic District, overlooking the Ohio River.

The Boy Scouts of America have the Simon Kenton Council, a division covering central Ohio to northern Kentucky.

The Simon Kenton Pub is a small bar located in the Water Wheel Restaurant at The Inn at Gristmill Square in Warm Springs, Virginia.