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In 1774 Judge Richard Henderson, a land speculator of North Carolina, hired Daniel Boone to blaze a trail through the Cumberland Gap into Kentucky. The Wilderness Road started at Bristol, Virginia (splitting off the Great Valley Road) and headed west along the Virginia-Tennessee border to the Cumberland Gap, across the nearby Cumberland River, and then went northwest to Boonesborough, Kentucky. Eventually, an extension of the road would reach Louisville, Kentucky on the Falls of the Ohio River.
The Kentucky legislature paid for the footpath to be upgraded to a wagon road starting in 1792. The wagon road was finished in 1796.
The opening of the National Road in 1818 provided an easier, more level route to the Ohio Valley and Kentucky. With the introduction of steamboats at about the same time traffic on the Wilderness Road declined until it was nearly abandoned in the 1840s. However, it was used by both Union and Confederate armies during the American Civil War.
- Bristol, Washington, Virginia
- Cumberland Gap at the juncture of Virginia, Tennessee and Kentucky
- Boonesborough, Madison, Kentucky
- Louisville, Jefferson, Kentucky
Settlers and Records
For partial list of settlers who used the Wilderness Road, see .
- Johnson, Robert Foster. Wilderness Road Cemeteries in Kentucky, Tennessee and Virginia. Owensboro, Kentucky: McDowell Publications, 1981. FHL US/CAN Book 973 V3j.