Moccasin Gap, or Big Moccasin Gap, is a rare natural pass through Clinch Mountain at Gate City in southwestern Virginia and has served as a mountain passage for centuries. Cherokee and Shawnee people used it to reach hunting grounds south of the Clinch River, and later it became a route for attacks and military movement in the Revolutionary and Civil wars. In 1775, Daniel Boone and thirty ax-men widened an existing Indian path here into part of the Wilderness Road, helping open an early route toward Cumberland Gap and Kentucky. Its relatively level terrain later supported westward travel, regional trade, rail construction, and modern highway development.