The Cumberland Gap is located near the point where Kentucky, Virginia, and Tennessee meet, between Middlesboro, Kentucky, and the town of Cumberland Gap, Tennessee. Thomas Walker discovered the pass in 1750. American frontiersman and hero Daniel Boone helped build the Wilderness Road, the first trail through the pass, in the 1770s. It became the main route used by pioneers moving west to settle the land beyond the Appalachian Mountains.

In 1940, 32 square miles (83 square kilometers) of the plateau, with the gap as the central feature, were reserved as the Cumberland Gap National Historical Park.