Featured
TRANSPORTATION · HISTORICAL MARKER
Gateway To Kaintuck
Transportation
5
For travelers on foot, the Appalachian Mountains seemed like an impenetrable wall six hundred miles long and one hundred fifty miles wide, but at Cumberland Gap there was both a good way in and a good way out of that rugged labyrinth of ridges, coves, and meandering streams. Woodland buffalo and parties of Cherokee and Shawnee moved north and south over this wilderness road for thousands of years. In the frontier era, longhunters and settler families followed those trails, climbing to the Gap and descending into Yellow Creek's valley. After passing Pine Mountain Narrows, they were well on their way toward the Kentucky bluegrass and the rich Ohio River bottomlands.
FIND IT
Middlesborough, Kentucky
CITY · 60 STOPSExplore Middlesborough, Kentucky
Hear every story as you drive
4.8 Stars · 800+ Ratings
© 2026 MainEngine