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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. An estimated 70,000 pioneers followed the path on foot or horseback into Kentucky and beyond before it was reopened as a wagon road in 1796.
- 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.