Location: Middlesboro
Top Restaurants in Middlesboro
Top Things to do in Middlesboro
- 1. Cumberland Gap National Historical Park
- 2. Abraham Lincoln Library and Museum
- 3. Tri State Peak Trail
- 4. Bell County Historical Society
- 5. Cumberland Gap Artists Co-op
- 6. Middlesboro Mall
- 7. Mitty's Metal Art
- 8. Shillalah Creek Wildlife Management Area
- 9. Cumberland Gap Off-Leash Dog Park
- 10. Oldest House in Middlesboro
Where to Eat in Middlesboro: The Best Restaurants and Bars
Middlesboro (locally /ˈmɪdəlzbɜːrə/) is a home rule-class city in Bell County, Kentucky, United States. The population was 10,334 at the 2010 U.S. census, while its micropolitan area had a population of 69,060.
Things to do in Middlesboro
1. Tasty Time
Overall Ratings
4.5 based on 12 reviews
Reviewed By Dee B - Cumberland Gap, TN
First of all, the rotating yogurt flavors and toppings are amazing! Love that they are always updated on Facebook. Staff is friendly and helpful. The best thing is that this place is so CLEAN! The decor is fun and modern and they also offer outdoor seating during certain hours. Definitely follow them on Facebook so that you can get updated on their current flavors!
2. Shades Cafe & Steakhouse
Overall Ratings
4.5 based on 109 reviews
We are a Cafe' that has soups, salads, sandwiches (paninis) and desserts in the "front" of the house. On Thursdays, Friday's , and Saturdays we also have a steakhouse menu that offers full sit down dinners and table service in the "back" of the house.....where we have three smaller, more private dinning rooms... We offer certified angus beef sirloin and ribeye steaks, salmon, shrimp, center cut pork chops, and grilled chicken. We also offer frapes, lattes, and most all hot and cold espresso based drinks.
Reviewed By Mary Ellen L - Joaquin, Texas
While returning from a drive to Cumberland Gap, we liked the reviews on Shades and decided to check it out. My husband is a real steak critic and declares the ribeye to be one of the best he has had, especially at a local steakhouse in such an humble setting. It was not prepared with a lot of extra seasoning which let the real flavor of the meat be the highlight. Our compliments to the cook.
3. Gap Creek Coffeehouse
Overall Ratings
5 based on 98 reviews
Reviewed By Pat A
This place has a post card atmosphere. Located in a beautiful small town at the base of Cumberland Mountain, an area filthy rich in American history. Great lunch spot with very creative daily specials and great coffee. Staff is super friendly, all the ingredients are fresh and most offerings are made to order. There is limited amount of indoor seating but when the weather permits the best choice is to grab a table outside next to the small creek that runs through the property. They're open evenings and the outdoor seating area is decorated in strings of bistro lights. With the creek this like the scene out of a romantic movie.
If you're in the area, this is definetly worth a stop. You won't be disappointed.
4. Pelancho's
Overall Ratings
4 based on 91 reviews
Reviewed By Evelyn S - Dallas, Texas and Vienna, Austria
Good hot sauce. Cheese quesadillas were tasty. Side of refried beans was enormous. Friendly service.
5. Dairy Queen
Overall Ratings
3.5 based on 11 reviews
Reviewed By SUBZEROSKIDD10 - Thetford, Vermont
I stopped into this Middlesboro Dairy Queen for some dinner. I was impressed with how quickly the food was prepared and that it was brought to us right at our table by the friendly employees. The fries were fresh and the burger nicely grilled. I look forward to returning to this DQ to try more from the menu and get one of their signature Blizzards.
6. The Pineapple Tea Room & Coffee Shoppe
Overall Ratings
4.5 based on 58 reviews
Reviewed By FNPinKnox
We were pleasantly surprised as we stopped in to ask if there was a location in Cumberland Gap that served breakfast and they did! Breakfast was delicious, a bunch of food, reasonably priced, great service! Great coffee selection although we had already had coffee earlier. Sounds like they also offer lunch, possibly dinner as well? Definitely worth checking out!
7. La Esperanza
Overall Ratings
4.5 based on 39 reviews
Reviewed By rentalwill - Middlesboro, Kentucky
We had our business meeting lunch there and there were 15 of us. We never ran out of anything thanks to their great wait staff. Always nice and friendly and food came out piping hot. I eat here every time I'm in town. Chicken Soup is awesome. Give it a try. Great food at a fair price
8. Sagebrush Steakhouse
Overall Ratings
4 based on 38 reviews
Sagebrush is a casual dining Steakhouse. Our menu is full of appetizing items with an emphasis on hand-cut steaks. We also offer award winning ribs, fresh seafood & chicken, as well as a variety of garden fresh salads, appetizers, homemade desserts and a full bar. We pride ourselves in serving a great meal with value & variety in a family friendly environment. Dine In - Take Out - Catering
Reviewed By LauraIngalls - Chennai (Madras), India
After going to the Cumberland Gap and Pinnacle Overlook, we were hungry and found the Sagebrush via TripAdvisor's app. And what a find! The parking is ample and free; the dining area is very spacious, with a separate (and apparently equally spacious) sports bar area....MoreThank you for your kind review. We are so glad you enjoyed your visit. We hope to see you again soon. Christine
9. Cracker Barrel
Overall Ratings
3.5 based on 82 reviews
Reviewed By Lori B - Philadelphia, Pennsylvania
Stopped in for the Wednesday nite special and was not disappointed. Service was good and the food typical of this chain.
10. Conley's Drive-In Restaurants
Overall Ratings
4.5 based on 16 reviews
Reviewed By DeniseBeth - Bristol, Tennessee
This is a drive-in...you park in their lot, they take your order at the car... First time there so we sampled the menu, and were not disappointed in anything. Chili cheese tots were smothered, but still crispy, and just-fried hot. Chili had great flavor and texture, yes a hot dog chili sauce style, but very good! My bacon cheeseburger was delicious, meat did not seem pre-shaped or frozen, it was a true fresh made home style burger. Quality lettuce topping, same with tomatoes and onions, generous topping portions as well. I got a plain dog, husband got loaded foot long, both were great, but it could stand alone. Buns were fresh too. Only got a sip of his shake, but great! We were there at peak lunchtime weekday, of course it took a few minutes, but everything was mad to order, and considering that, it wasnt a long wait. Our waitress was very fast to notice us and take care of us. Perfect local spot we found while passing through, wish it were a chain so i could have it again!
