Where to Eat in Middlesboro: The Best Restaurants and Bars

April 15, 2018 Ying Subia

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

300 N 12th St Ste 2, Middlesboro, KY 40965-1171 Seating
Excellent
59%
Good
25%
Satisfactory
8%
Poor
8%
Terrible
0%
Overall Ratings

4.5 based on 12 reviews

Tasty Time

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

2119 Cumberland Ave, Middlesboro, KY 40965-2874 Reservations, Takeout, Private Dining, Seating, Waitstaff, Parking Available, Street Parking, Free Off-Street Parking, Accepts American Express, Accepts Mastercard, Accepts Visa, Free Wifi, Accepts Discover, Highchairs Available, Wheelchair Accessible, Accepts Credit Cards American, Steakhouse, Cafe, Gluten Free Options Lunch, Dinner SGD 9 - SGD 39 +1 606-248-4315
Excellent
76%
Good
17%
Satisfactory
4%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 109 reviews

Shades Cafe & Steakhouse

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

710 Pinnacle Aly, Cumberland Gap, TN 37724-4771 Takeout, Outdoor Seating, Seating, Parking Available, Wheelchair Accessible American, Cafe Breakfast, Lunch, Brunch, Dinner +1 423-801-3100
Excellent
82%
Good
14%
Satisfactory
4%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 98 reviews

Gap Creek Coffeehouse

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

605 N 12th St, Middlesboro, KY 40965-1129 Takeout, Seating, Waitstaff, Television, Wheelchair Accessible Mexican, Southwestern Lunch, Dinner +1 606-248-0303
Excellent
44%
Good
39%
Satisfactory
8%
Poor
5%
Terrible
4%
Overall Ratings

4 based on 91 reviews

Pelancho's

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

100 N 12th St, Middlesboro, KY 40965-1027 Seating Fast Food Dinner +1 606-248-8730
Excellent
37%
Good
18%
Satisfactory
27%
Poor
9%
Terrible
9%
Overall Ratings

3.5 based on 11 reviews

Dairy Queen

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

604 Colwyn Ave, Cumberland Gap, TN 37724-5002 Takeout, Seating, Waitstaff, Wheelchair Accessible American, Cafe, Vegetarian Friendly, Vegan Options, Gluten Free Options Breakfast, Lunch, Dinner, Brunch +1 423-869-4410
Excellent
63%
Good
25%
Satisfactory
6%
Poor
3%
Terrible
3%
Overall Ratings

4.5 based on 58 reviews

The Pineapple Tea Room & Coffee Shoppe

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

12th St, Middlesboro, KY 40965 Takeout, Seating, Waitstaff, Wheelchair Accessible Mexican Lunch, Dinner +1 606-248-0901
Excellent
55%
Good
28%
Satisfactory
12%
Poor
0%
Terrible
5%
Overall Ratings

4.5 based on 39 reviews

La Esperanza

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

910 N 12th St, Middlesboro, KY 40965-1832 Takeout, Seating, Waitstaff, Parking Available, Free Off-Street Parking, Television, Highchairs Available, Wheelchair Accessible, Accepts American Express, Accepts Mastercard, Accepts Visa, Free Wifi, Accepts Discover, Outdoor Seating, Serves Alcohol American, Steakhouse, Bar Lunch, Dinner, Drinks SGD 7 - SGD 26 +1 606-302-4208
Excellent
39%
Good
34%
Satisfactory
18%
Poor
7%
Terrible
2%
Overall Ratings

4 based on 38 reviews

Sagebrush Steakhouse

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

1049 N 12th St, Middlesboro, KY 40965-1829 Takeout, Seating, Waitstaff, Parking Available, Highchairs Available, Wheelchair Accessible American Breakfast, Lunch, Brunch, Dinner +1 606-248-7011
Excellent
37%
Good
24%
Satisfactory
20%
Poor
10%
Terrible
9%
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

708 E Lothbury Ave, Middlesboro, KY 40965-1138 Takeout, Wheelchair Accessible Fast Food Lunch, Dinner +1 606-248-1741
Excellent
51%
Good
43%
Satisfactory
0%
Poor
0%
Terrible
6%
Overall Ratings

4.5 based on 16 reviews

Conley's Drive-In Restaurants

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!

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