Route of the Wilderness Road
Of Kentucky's 75,000 population in 1790, about 90% had arrived by way of the Wilderness Road.
The Cumberland Gap is about 510 highway miles from Washington D.C.

Located at the Virginia-Tennessee border, the little village of Cumberland Gap, TN, is about 25 miles farther west than the meridian of Detroit, Michigan. Today, Cumberland Gap National Historical Park  commemorates Daniel Boone and the surge of people who traveled westward after the Revolution.

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.