Moccasin Gap in Clinch Mountain links the valleys of the Holston and Clinch Rivers. The main trail between Cherokee territory to the south and Shawnee lands in present-day Ohio passed through it, and by the mid-18th century hunters and explorers of European descent were using the gap. In 1775 Richard Henderson, a land speculator, hired Daniel Boone to clear a route to Kentucky, and Boone and 30 men widened the existing Indian path to create the Wilderness Road, over which thousands of settlers later passed. The arrival of the railroad in the 1880s and the construction of U.S. highways in the 20th century ensured that Moccasin Gap remained a significant transportation route.