The Wilderness Road & Cumberland Gap

The Wilderness Road

and the Cumberland Gap

Map of the Wilderness Road

Route of the Wilderness Road

Some suggest that the origin of the Wilderness Road was at Fort Chiswell (Ft. Chissel) on the Great Valley Road where roads converged from Philadelphia and Richmond.

Others claim the Wilderness Road actually began at Sapling Grove (now Bristol, VA) which lay at the extreme southern end of the Great Valley Road because it was at that point that the road narrowed, forcing travelers to abandon their wagons.

It moved through the Allegheny Mountains at Cumberland Gap, at what is now the junction of the State boundaries of Kentucky, Tennessee and Virginia.

Heading northwest, it splits at Hazel Patch--with one route creating Boonesborough, the other Frankfort.

Today one can follow the main route from Bristol, VA to Middlesboro, KY then to Pineville, Mt. Vernon, and on towards Lexington on Interstate 75.

Downoad a 2-page Fact Sheet (free) about this trail in PDF format.

The Wilderness Road

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