The Wilderness Road served as the principal route from the east coast colonies to the interior lands drained by the Ohio River. The configuration of the Wilderness Road may be described as a broad loop, open on the north. Its eastern leg begins in Virginia near the Potomac River, stretches down the Shenandoah Valley to Staunton, and then to the Holston River, continuing to Long Island (Kingsport). The southern base of the loop extends west to Cumberland Gap and finally swings northward to the falls of the Ohio at Louisville, Kentucky. Historically, the best known segment of the road ran from the Long Island of the Holston to the Bluegrass area of north-central Kentucky by way of Cumberland Gap.
Prior to commercial and settler traffic, migrating herds of bison seeking the numerous salt licks that dotted Kentucky and Virginia beat out a well-defined trace, and Native Americans traveling between villages and hunting grounds heavily traversed the route. Travelers could follow such traces on roads extending from near Roanoke, Virginia, to central Illinois. Foremost among the Indian routes in the eastern United States was the Warriors Path, which looped southward through the Gap connecting the Ohio Valley with the Shenandoah and Potomac Rivers. Branches of the road continued southeast to the Cherokee and Creek settlements. Daniel Boone traveled along the road in 1769, returning in 1775 to mark it for land speculator Richard Henderson. Remnants of this early road, variously known as the lower Virginia Road, upper Virginia Road, and Kentucky State Road, are still visible.
The Wilderness Road brought travelers, skilled craftsmen, and “outside” ideas into areas across the Appalachian Mountains. Demand for improvements became a constant complaint as settlers and commercial traffic increased following the American Revolution. The route was the most direct and easiest path from the lower Ohio Valley to Philadelphia until the opening of the Erie Canal and roads across the mid-Atlantic states during the 1830s. Livestock drovers from Kentucky followed the road and its branches into the southeastern states. After 1834 a stage from Bean Station to Lexington, Kentucky, operated three times a week over the Wilderness Road, carrying freight, mail, and passengers. During the Civil War, many defensive positions imprinted the landscape, though General Ulysses Grant dismissed the road as useless for military purposes.
A semblance of order returned after the war, and modern roads began to cover the Wilderness Road by the turn of the twentieth century. Subsequently, an Object Lesson Road, then state and federal highways replaced the Wilderness Road. Efforts to locate the historic road using modern remote sensory techniques and historic accounts by travelers continue, however. The most ambitious attempt, at Cumberland Gap National Historical Park, will restore a portion of the Wilderness Road through Cumberland Gap to its 1780-1810 appearance, including vegetation along the route. The restoration project follows the construction of twin tunnels through the mountains, connecting Kentucky, Virginia, and Tennessee.
Katherine R. Barnes, “James Robertsons Journey to Nashville: Tracing the Route of Fall 1779,” Tennessee Historical Quarterly 36 (1976): 145-61; Robert L. Kincaid, The Wilderness Road (1947; reprints, 1955 and 1966) and “The Wilderness Road in Tennessee,” East Tennessee Historical Society Publications 20 (1948): 37-48