The gap is a notch in Cumberland Mountain where Tennessee, Kentucky and Virginia meet, and the people who used it first were Native. Cherokee and Shawnee travelers followed a game trail through it that settlers called the Warriors' Path, across hunting ground claimed by the Shawnee to the north and the Cherokee to the south. Thomas Walker brought the pass to settlers' notice in 1750 and named it for the Duke of Cumberland.
In 1775 Daniel Boone, hired by the Transylvania Company that had just bought Cherokee land at Sycamore Shoals, led axmen from Long Island of the Holston through the gap and widened the trail into the Wilderness Road. Before 1810 an estimated 200,000 to 300,000 settlers passed this way into Kentucky and the Ohio Valley. The road was dangerous. In the fall of 1784 Chickamauga warriors under Dragging Canoe ambushed travelers between the gap and Crab Orchard, killing more than 100 people. In the Civil War the gap changed hands four times.
The Tennessee town below it, Cumberland Gap, has about 300 residents, and most of its downtown is a National Register historic district. Alexander Arthur built a railroad tunnel here in 1888. Twin tunnels opened in 1996 and carry US-25E under the mountain, which took through traffic off the town's streets. The national historical park is run from Middlesboro, Kentucky, and has fortifications and walking trails above the town.
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