The Perfect Fall Road Trip in Kentucky!

Fall is the perfect time to take a break from the ordinary and explore the beauty that surrounds you. Across Kentucky, there are many roads that can lead to a perfect fall road trip, but the one suggested below is part of the Wilderness Road Heritage Scenic Byway. Whether you take two hours or two days to complete the drive from Middlesboro to Berea, you’ll find places listed where you can step out of your car and walk along some historic trails, enjoy an authentic Kentucky meal, look for ghosts, or spend a quiet evening relaxing and enjoying the sounds of nature. 

1. City Sippers, Middlesboro, KY

Simple. Good. Coffee. What more do you need to know about City Sippers? Open bright and early at 7:30 a.m. every day but Sunday, this little coffee shop located near Southern Kentucky Community & Technical College is a hidden gem, and has just the right cup of coffee to kick start your road trip. 

2. Pine Mountain Resort State Park, Pineville, KY

You’ll have your choice of 14 different trails to discover at Pine Mountain Resort State Park in Pineville. Several of the trails can be biked as well, and range in hiking difficulty from easy to strenuous and in length from a half-mile to almost two miles. Each trail has its own beauty, such as the Hemlock Garden Trail with its giant sandstone boulders overlooking you as you meander alongside the little woodland streams. The small of rhododendrons fill the air and the trees are like red matchsticks in the fall. There’s so much to do at Pine Mountain, and you’ll easily fill the good part of the day with hiking, miniature golf, and just enjoying the gorgeous fall weather.  

View from one of the overlooks at Pine Mountain last October.

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3. Pine Mountain Zipline Canopy Tour, Pineville, KY

Whether you decide to take a break for lunch before continuing your adventure at Pine Mountain or want to keep going, a trip to Pineville wouldn’t be complete without making time to experience the Zipline Canopy Tour and see what life is like in the trees. You’ll be fastened securely to a tethered cable that takes you high above a mix of 300-year-old pine and hemlock trees bursting with color, past beautiful waterfalls rushing below, two swinging bridges, a spiral staircase, and finally to a soft landing below. The whole tour takes a little over two hours. Weight restrictions apply and you’ll want to wear comfortable loose-fitting clothing. 

4. Flocoe on the Square, Pineville, KY

No doubt you’ve worked up quite an appetite and need a hearty meal. You’ll find the best barbecue pulled pork sandwiches west of the Mississippi at Flocoe on the Square. The chicken salad and onion rings are excellent too, but you can’t go wrong with anything you order. If they have it and you’re still hungry, try the peach cobbler. You won’t regret it. 


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5. Dr. Thomas Walker State Historic Site, Barbourville, KY

The winding country road that takes you to Dr. Thomas Walker State Historic Site in Barbourville is worth the trip even if you’ve never heard of its namesake. Even before Daniel Boone started exploring the land in and around what would become the Commonwealth of Kentucky, Dr. Walker visited and built a cabin much like the one that’s in the park. Open year-round, you can freely explore the house and grounds and learn more about the original explorer.

6. Warfield Cemetery, Barbourville, KY

While you’re taking a little detour on your road trip to visit the Dr. Thomas Walker State Historic Site, you might as well journey to the little country resting place, Warfield Cemetery. Off the main road, as soon as you turn in the lane that leads to the graveyard on the left, you’ll see dozens of headstones of all shapes and sized dotting the countryside. Since it is fall and Halloween is just around the corner, this may be a good place to stop and see if you see or hear any of the otherworldly sights and sounds that have been reported. This seems like a nice place for a quiet visit. Or does it?

7. DuPont Lodge, Corbin, KY

Park of the Reader’s Choice Awards, Cumberland Falls State Resort Park is a great place to spend the night. From the moment you walk inside the DuPont Lodge, you’ll feel the warm comfort of pine surrounding the two-story lodge and if it’s a chilly evening, the fireplace may be lit. One of the unique things about this rustic lodge is that the moonlight creates a halo around the 68-foot waterfalls, making a magical moonbow on clear nights. 

Our digs tonight #history #dupontlodge #cumberlandfalls #kentucky #datenight

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8. The Wrigley Taproom & Brewery, Corbin, KY

If you like the idea of grabbing a cold one and listening to live music before turning in for the night, head on down to the Wrigley Taproom & Brewery in Corbin. This amazing little farm-to-table eatery serves up a simple, but tempting menu items like Buffalo lime wings, smoked salmon BLT taco, and a three-cheese grilled cheese. They also offer a good selection of beer to quench your thirst, but make sure you save room for the coconut mango waffle. 

9. 4th Street Coffee House, London, KY

Whether you’re looking to eat in or grab something quick to take with you as you continue your fall road trip, 4th Street Coffee House will satisfy your cravings. With the best coffee in town, fast service, and friendly staff, it’s no wonder this place is so popular. And if coffee isn’t your thing, they have delicious protein shakes and smoothies that will energize you for the day. 

10. Berea Farmers Market, Berea, KY

Open year-round, the Berea Farmers Market will give you a chance to pick up some locally grown and produced fruits and vegetables to take home after your fall road trip. Besides in-season items like banana peppers, apples, and pumpkins, there’s baked goods, and arts and craft items for sale. 

11. Daniel Boone National Forest

On this leg of your perfect fall road trip, Daniel Boone National Forest near Berea is the destination. The nearly two million acres of land is completely within the state border, making it the only forest that meets achieves that. Named after one of our country’s most well-known and well-loved early pioneers, there are enough activities to keep you busy for the day or a week. There are caves to explore, two official wilderness areas to hike, two rivers to navigate that comprise over 27,000 acres and more than 20 miles of trails. 

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