Featured
TRANSPORTATION · HISTORICAL MARKER
Gateway to Kaintuck
Middlesborough, Kentucky
· Cumberland Gap National Historical Park
Transportation
4
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 passed north and south over this wilderness road for thousands of years. Frontier-era longhunters and settler families followed their trails, climbing up to the Gap and dropping into Yellow Creek's valley. Once past Pine Mountain Narrows, they were well on their way to 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