Three Favorite Trips for Fall

Our Travel editors share their favorite fall places to visit

Cumberland Gap, KY
Hand-hewn wooden fences once kept livestock from the fields. Now they corral the colors of the season.

Sometimes we find fall in unexpected places. When we do, we like to tell you about our discoveries. These spots make the region proud when it comes to blazing color. You’ll also experience so much more than the brilliant foliage. One of Kentucky’s highest points shelters buildings from a long-gone settlement, along with an unparalleled view. An upscale South Carolina city harbors an amazing urban park in its midst. And Oklahoma offers up a lively festival to match the crisp air. Give these fall destinations a try; you’ll find them worthy of further exploration this harvest season.

1. Cumberland Gap, KY
by Les Thomas

When I travel, I like to be comfortable. I would have made a lousy pioneer. But as I stand in their footsteps in the embrace of the Cumberland Gap on this autumn morning, I realize I have something in common with them. They didn’t like crowds either. That’s why I slipped away to Cumberland Gap National Historical Park, where Kentucky, Tennessee, and Virginia meet. I wanted to leave the bustle of the city for a getaway that isn’t overrun with tourists.

Room To Roam
“This park is a gem off the beaten path. We get a lot of people who are trying to escape the crowds of the Smokies,” ranger Scott Teodorski says. “It’s a nice piece of wild mountains.”
It was a snap to get here. I only had to drive two hours on the interstate south of Lexington, Kentucky, and then take an easy 20-minute walk to stand in the saddle of America’s first mountain retreat. Up to 300,000 pioneers―ancestors to millions of us in the South―passed this way. I watch a lacy curtain of clouds melt away and think of what this view once meant to them. It was the promise of a new frontier. “It’s hard to imagine Kentucky being the Wild West,” says Scott, “but in those days it was.”

Mighty efforts have gone into restoring the wilderness during the past 10 years. The largest project rerouted U.S. 25E through a nearly mile-long tunnel so the Cumberland Gap could return to the rustic path it once was. More than half of the national park’s 24,000 acres is wilderness.

Discover a Lost Village
One morning, I head over to the national park to see a secret place that many travelers often miss. The gap is the centerpiece of the park, but part of its soul rests atop one of Kentucky’s highest mountains, where Scott and other rangers take visitors on guided tours. We drive to Hensley Settlement on a winding gravel road that makes the Blue Ridge Parkway seem like a superhighway. A sourwood tree, bright as a Roman candle, gleams in the light that bathes a rustic schoolhouse and the weathered cabins of the settlers who once lived here. “The thing that makes it unique is that it’s isolated even to this day,” Scott says. “The solitude is wonderful.”
Autumn whispers a benediction over these mountains. Sunlight dances on tawny meadows. On a day like this one, it’s paradise.

Going to the Gap
Cumberland Gap National Historical Park: U.S. 25E, P.O. Box 1848, Middlesboro, KY 40965; or (606) 248-2817. Visitors center hours: 8 a.m.-5 p.m. daily. Tours to Hensley Settlement continue daily through October 31. Reservations are required. Admission: $10 adults, $5 ages 12 and under. Bring bottled water, snacks, warm clothing, and comfortable shoes. The tour lasts about four hours.

Autumn Activities

  • October 3-5―Cumberland Mountain Fall Festival: Middlesboro Arts and crafts festival with live entertainment, kids’ stage, petting zoo, and lots of food;
  • October 11 and October 18―Elk Viewing Tour: Pineville Guided elk tours at Pine Mountain State Resort Park; or (606) 337-3066.


  • Interpretive Center at Pine Mountain State Resort Park: Learn about the area of Pine Mountain, the wildlife, and the plants that turn golden in fall. An interactive kiosk and exhibits help tell the story of the park; or (606) 337-3066.
  • Gap Cave Tours: Explore a cave, along with park rangers, on this 1.5 mile tour located at the Cumberland Gap. Two hours of stalagmites, cascades, and maybe a bat or two await. No children under 5. Tickets: $8 adult, $4 ages 5-12; or (606) 248-2817.
  • Abraham Lincoln Library and Museum: Just a few minutes away in Harrogate, Tennessee, sits a repository filled with amazing Abraham Lincoln memorabilia. Included in the artifacts are the cane Lincoln carried to Ford’s Theatre and a tea set belonging to Lincoln and wife Mary Todd; 6965 Cumberland Gap Parkway, Harrogate, TN; or (423) 869-6235.


  • Holiday Inn Express: 1252 North 12th Street, Middlesboro, KY 40965; (606) 248-6860. Rates start at $79.95.
  • Pine Mountain State Resort Park: U.S. 25E, 2 miles south of Pineville; (606) 337-3066. Rates start at $104.95.


  • Avenue Café & Antiques: 1915 West Cumberland Avenue, Middlesboro, KY; (606) 248-3958. Known for its daily specials and home cooking, this bistro also has great knickknacks and antiques for sale. Try the homemade chicken salad and soup.
  • The Flocoe: 122 West Kentucky Avenue, Pineville, KY; (606) 337-2034. Another local favorite, this spot offers down-home cooking at its finest. Don’t miss the chicken and dumplings.
  • Webb’s Country Kitchen: 527 Colwyn Avenue, Cumberland Gap, TN 37724; (423) 869-5877. This is biscuits-and-gravy land. Open for three meals a day; check out the Pinto Special at lunch, which comes with beans, greens, fried potatoes, cornbread, and onions.


  • Nothins Perfect Craft Store: 521 Colwyn Avenue, Cumberland Gap, TN 37724; or (423) 869-4410. Pick up some primitive dolls, candles, or potpourri.
  • The Cumberland Gap General Store: 503 Colwyn Avenue, Cumberland Gap, TN; or (423) 869-2282. More than 6,000 items fill this fun spot, including chimes, gnomes, teddy bears, and kitchen items.