Wilderness Road

Wilderness Road Immediately after helping negotiate the treaty of Sycamore Shoals, Daniel Boone and eight axmen blazed this road from the Holston River in Tenn., via Cumberland Gap, to the Kentucky River in spring 1775. Forking off from the Great Wagon Road at Roanoke, Va., it was the southern route westward for pioneers who could not make the easy trip via the Ohio River. It was not improved to carry wagon traffic until 1795.