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    A summary of what Cumberland Gap has to offer.

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    Miss the Kentucky Derby and it's still possible to see plenty of derby-related sights in the Bluegrass State, also host to bourbon distilleries and cultural sights.

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Cumberland Gap, Kentucky - Scenic Drives

Byways, Backways, Historic Routes,...

Scenic drives to consider in the Cumberland Gap area are listed below. Click on any scenic byway or backway listed below for complete information.

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2 scenic drive Results

More Info Pine Mountain Road

Enjoy Eastern Kentucky`s legendary beauty as you drive over the crest of 2,800-foot high Pine Mountain and the Little Shepherd Trail.

More Info Wilderness Road Heritage Highway
  • Two hours to drive or two days to visit places along the way.
  • 93.8 miles (151 km)

Trace the footsteps of early pioneers and explorers along the Wilderness Road Heritage Scenic Byway. From panoramic views of the Appalachians in the Cumberland Gap National Historic Park, to a community culture centered on folk art and mountain music, the Byway is packed with reasons to immerse you...

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Cumberland Gap, Kentucky - Scenic Drives

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