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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, a western spur of the road would reach Harrodsburg, and then Louisville, Kentucky on the Falls of the Ohio River.
The road crossed difficult mountains, rushing rivers, and ran through Indian lands. Both hostile Indians and white robbers were problems, so many people chose to travel the road in large groups. But the risks were worth taking for the rewards of bountiful hunting grounds, rich farmland, and good salt licks.
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
Later west fork:
- Harrodsburg, Mercer, Kentucky
- Louisville, Jefferson, Kentucky
Settlers and Records
Scots-Irish and Germans were the first to use the Wilderness Road in large numbers. 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.