In 1769 Boone blazed the first known trail from North Carolina to Tennessee. Boone spent the next two years hunting and exploring in Kentucky, where he was captured twice by Indians and escaped both times. In 1773, Boone attempted to settle in Kentucky but an Indian attack resulted in the death of his oldest son James. Two years later he succeeded in founding Boonesboro (near Lexington, Kentucky), the first settlement of Transylvania. Continued fighting with the Shawnee and the British resulted in the loss of his second oldest son Israel during one of the last battles of the American Revolutionary War, the Battle of Blue Licks.
Many anecdotes of Boone folklore are recorded. His rifle was a Kentucky Long Rifle he named Tick-Licker. He wore a coonskin hat and buckskin clothes with fringed leather trim. He never admitted to being lost; however, he once reported that he was "confused for several weeks." He was captured by the Chief Black Fish of the Shawnee Indians, but escaped when he learned of a British and Indian plot to attack Boonesborough. He rallied the settlers and successfully repelled a 10-day siege of Boonesborough. The publication of "The Adventures of Colonel Daniel Boon" in 1784 by John Filson immortalized Boone the frontiersman as an American legend and a true folk hero.
Boone lost most of his land claims in Kentucky due to faulty titles. Taxes and creditors forced him out of Kentucky and in 1788 Boone settles at Point Pleasant on the Ohio River in what is now West Virginia. His son Daniel Morgan Boone met with the Spanish lieutenant governor Don Z.Trudeau in 1798 and was invited to settle the Boone family in Missouri. Two years later Boone was appointed "syndic" (judge and jury) and commandant of the Femme Osage region. Rebecca died in 1813 and Daniel Boone died at his home in Defiance, Missouri on September 26, 1820.