We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cumberland Gap

Free Newsletter

Interested in Cumberland Gap?

We'll send you updates with the latest deals, reviews and articles for Cumberland Gap each week.

We remove posts that do not follow our Trip Lists guidelines.
We reserve the right to remove any lists for any reason.
Trip List by KimRenee

Home Cooked meals & nature

Mar 30, 2007  Family from the tri-state area.
4.5 of 5 stars based on 1 vote

Webbs Kitchen, in Cumberland Gap (2 miles east on 23E from Middlesboro, thru the tunnel) has the *best* home cooked food. Drive up to the Pinnacle and overlook 3 states, hike behind the visitors center, hike the creek trail behind Webbs Kitchen, hike the leisurely Pine Mtn trails or toughen up for the Daniel Boone trails near the town of Cumberland Gap. Reserve a morning tour at the Gap Cave (at the visitors center) and enjoy nature and history.

  • Category: Best of
  • 1. Webb's Kitchen, hiking,

    Home cooked southern food in a tiny leisure town full of history. Great food, great prices, great service, bluegrass jams on Friday & Saturday nights. Can't beat the catfish, burgers & breakfast. Walk off this big meal on the easy Iron Furnace trail that strolls beside a gorgeous creek running out of the top of the mountain. Then go back in Webb's for the best cobbler since Gramma's.

  • 2. Pinnacle Overlook

    Drive up a winding road to the beautiful Pinnacle Overlook. See 3 states and a gorgeous overview. Hikes for all available: easy, medium, hard. Go to the Cumberland Gap Visiters Center by the 23E tunnel for more info.

  • 3. Gap Cave

    Tour through the historic cave. Reservations can be made at the Cumberland Gap Visitors Center near the 23E tunnel. Beautiful formations along with Cherokee and Civil War history are affordably accessible.