One of the nation's most historic routes, the Wilderness Trail was blazed by Daniel Boone in 1775. The trail started at Long Island located in the Holston River (Kingsport, TN) and wound its' way through Southern Virginia and Cumberland Gap ending in Kentucky. It would become the route for hundreds of thousands of settlers of the western frontier. Long before Columbus settled America, the Wilderness Trail was a major link in the trail systems of the Indians on the North American continent, used for commerce and raids. Gabriel Arthur, a young indentured servant, was first of record to travel the route and see the Cumberland Gap, a natural break in the mountains. Arthur was sent along the trail in 1674 by the Shawnee Indians to secure a trade agreement with settlers.

Location: Trail begins at Netherland Inn - Kingsport
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Website: http://www.danielboonetrail.com/