Route
The route of the Wilderness Road made a long loop from Virginia southward to Tennessee and then northward to Kentucky, a distance of 200 miles (320 km).
From The Long Island of the Holston River (modern Kingsport, Tennessee), the road went north through Moccasin Gap of Clinch Mountain, then crossed the Clinch River and crossed rough land (called the Devils Raceway) to the North Fork Clinch River. Then it crossed Powell Mountain at Kanes Gap. From there it ran southwest through the valley of the Powell River to the Cumberland Gap.
After passing over the Cumberland Gap the Wilderness Road forked. The southern fork passed over the Cumberland Plateau to Nashville, Tennessee via the Cumberland River. The northern fork split into two parts. The eastern spur went into the Bluegrass region of Kentucky to Boonesborough on the Kentucky River (near Lexington). The western spur ran to the Falls of the Ohio (Louisville). As settlements grew southward, the road stretched all the way to Knoxville, Tennessee, by 1792.
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