The most daring effort to colonize the rich lands of the Kentucky River area were those of Colonel Richard Henderson, a Superior Court judge of North Carolina. Henderson decided that the best way to secure the area was to deal directly with the Cherokee Indians. He discussed his plans with friends and they formed the Transylvania Company and solicited the assistance of Boone in negotiating with the Indians and blazing the trail. Boone was no stranger to the Kentucky territory, having made several trips through the area. He wanted to make his home in Kentucky and was quick to accept Henderson’s offer.
They found the Cherokee willing to sell the land between the Cumberland and Kentucky Rivers for 5 tons of serviceable goods. Final negotiations were held at Sycamore Shoals (now Elizabethton, TN), an ancient Cherokee treaty ground on the southern bank of the Watauga River, about 15 miles southeast of Long Island on the Holston, a sacred area to the Indians. After the agreement, Boone left for Long Island on the Holston to rendezvous with 30 armed and mounted axmen, among them his brother Squire, and son-in-law William Hays.
On March 10, 1775, Boone led his trail blazers from Long Island to cut the trail through some 200 miles of wilderness northwest through the Cumberland Gap and into Kentucky.
Boone was born in Pennsylvania in 1734. His family ventured into the Yadkin Valley of North Carolina in 1750 when Boone was 15. Four years later, he fought in the French and Indian War. A skilled woodsman, crack shot and tireless wayfarer, Boone later served two terms in the Virginia General Assembly, kept a tavern, led wars against the Shawnee Indians and continually moved around to escape what he called the “too crowded” conditions of 18th century Kentucky.
This driving tour follows the Wilderness Trail to Cumberland Gap as closely as is possible. This guide is arranged by stops, beginning at the Long Island of the Holston near the historic Netherland Inn.