Legends of The Kentucky Wildlands Itinerary

Take a step back in time and explore some of the great legends of The Kentucky Wildlands. To explore the locations featured in this itinerary, scroll down.

Day 1:

See – Start your day at Cumberland Gap National Historic Park in Middlesboro. See where the legendary Daniel Boone blazed a trail through the Cumberland Gap, creating the Wilderness Road and the first great gateway to the west. Activities include sightseeing, guided tours, hiking and camping. 

Eat – The Harland Sanders Café and Museum is not your typical KFC. It is the Birthplace of Kentucky Fried Chicken, where Colonel Sanders created his original recipe back in 1940. Enjoy the history and even get your picture made with the Colonel sitting on a park bench.

Take a step back in time to Conley's Drive-in Restaurant in Middlesboro. Conley’s is said to have one of the best “foot-long” hot dogs in the region. Don’t forget to top your meal off with an old-fashion soda or milk shake.

Dairy Cheer, home of the Smashburger, has locations in Pikeville or Prestonsburg.

To satisfy your sweet tooth give Anita Bite Dairy Bar in Pikeville a try. It’s a pretty good bet that you will find something to satisfy that sweet craving.

Stay – Evans Lodge is an old stone and wood lodge at Pine Mountain State Resort Park and is Kentucky’s first state park. The resort park, located in Pineville, offers plenty to do from hiking the famous Chained Rock Trail to playing 18 holes of golf in the mountains.

Day 2

See – The Hatfield & McCoy Driving Tour is a self-guided tour that includes historical sites of the feud in both Kentucky and West Virginia. The tour takes you through the beautiful mountains of eastern Kentucky.

EatPig in a Poke is said to serve up some of the best BBQ in Kentucky including pulled pork and chicken, slow smoked brisket and tender fall off the bone baby back ribs.

Billy Ray's Restaurant is home to the “Original Pool Room Hamburger.” If a hamburger is not what you are looking for try the delicious prime rib or county fired steak or the hearty open-faced roast beef.

Lizzie B's Cafe & Bakery is like no other place in the region and is a local favorite. Its unique eclectic atmosphere provides a great place to relax for sandwiches on homemade bread, pizza and soups. Lizzy B’s also has a full coffee bar, deserts, beer and wine.

Stay – Stay in the lodge at Jenny Wiley State Resort Park overlooking Dewey Lake or camp at one of the two campgrounds. The park offers activities from boating and fishing to mountain biking Sugar Camp Mountain and Dawkins Line Rail Trail. Tip: try the signature catfish or legendary Kentucky hot brown in the Music Highway Grill Restaurant.

Day 3

See- Spend the day traveling along U.S. 23 known as the County Music Highway. U.S. 23 is hallowed ground for music and storytelling legends including Loretta Lynn, Crystal Gayle, The Judds, Ricky Skaggs Dwight Yoakam, Keith Whitley and Patty Lovelace. This scenic road travels along the Kentucky-West Virginia boarder. Take time to stop at museums that celebrate not only the legends in music but coal mining as well.

Eat – Grab a burger at Fat Patty's in Ashland or some Award winning ribs at Smokin' J's Rib and Brewhouse.

Featured in this Itinerary

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