Where to eat between Simpsonville (Kentucky) and Charleston (West Virginia)

This food trip itinerary gives you restaurant recommendations for places to eat over 2 days. Starting from Simpsonville, you can leave at 10:20 am and drive for about 40 minutes to the first stop.

5711 McCracken Pike
Frankfort, KY
(859) 879-0101
$$
  250 reviews
Southern food
11am to 8pm
Day 1. Arrive at 11:00 am. Eat for about 2 hours. Then drive for about 30 minutes.
362 E Main St
Lexington, KY
(859) 309-3039
$$
Arrive at 1:30 pm. Eat for about 2 hours. Then drive for about 30 minutes.
410 Boone Ave
Winchester, KY
(859) 385-4479
$
Arrive at 4:00 pm. Eat for about 2 hours. Then drive for about 40 minutes.

Owingsville, KY
(606) 336-5095
Arrive at 6:40 pm. Eat for about 2 hours. Stay overnight. The next day, leave at 8:30 am. Then drive for about 30 minutes.
313 Flemingsburg Rd
Morehead, KY
(606) 780-4282
$
  36 reviews
Bakeries, Cafes, Sandwiches
9am to 5pm
Day 2. Arrive at 9:00 am. Eat for about an hour. Then drive for about 30 minutes.
561 E Tom T Hall Blvd
Olive Hill, KY
(606) 315-2025
  26 reviews
Breakfast & Brunch, Burgers, Donuts
6am to 7pm
Arrive at 10:30 am. Eat for about 2 hours. Then drive for about 50 minutes.
252 Main St
Ceredo, WV
(304) 453-3000
$$
  75 reviews
Italian restaurants
Arrive at 1:20 pm. Eat for about 2 hours. Then drive for about 50 minutes.
1156 US 35 N
Winfield, WV
(304) 937-2855
$
Arrive at 4:10 pm. Eat for about 2 hours. Then drive for about 40 minutes.
1038 Bridge Rd
Charleston, WV
(304) 343-5652
$$
  177 reviews
Pizza, Salad
11am to 10pm
Arrive at 6:50 pm. Eat for about 2 hours. Then drive for about 5 minutes.

Reach your destination in Charleston around 8:50 pm after eating at 9 restaurants over 2 days. If you were to drive nonstop, it would take about 3½ hours driving roughly 224 miles straight to Charleston (West Virginia). Looking for more restaurants? You can choose a category below if you want to do an entire road trip full of Southern food, Breakfast & Brunch, Burgers, American restaurants (Traditional), Caribbean food, Bakeries, or more. Enjoy the journey!

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