What mountain pass connects Virginia, Kentucky, and Tennessee?

The Cumberland Gap is the mountain pass that connects Virginia, Kentucky, and Tennessee. It cuts through the Cumberland Mountains of the Appalachians near the three states’ meeting point and has long served as a natural route through the mountain range.

Native American peoples used the passage before European settlement. Virginia explorer Thomas Walker publicized the route in 1750, and Daniel Boone later led workers who widened the trail in 1775. The resulting route became part of the Wilderness Road, through which settlers traveled into Kentucky and the Ohio Valley.

The pass is near the present-day communities of Middlesboro, Kentucky, and Cumberland Gap, Tennessee. Geographically, the actual pass lies on the Kentucky–Virginia border, close to—but not exactly at—the tri-state marker with Tennessee. That detail sometimes causes confusion in simplified descriptions saying the pass is “in” all three states.

Today the site is protected within Cumberland Gap National Historical Park. U.S. Route 25E once crossed the pass directly, but the Cumberland Gap Tunnel, completed in 1996, now carries the highway beneath the historic route.