3 Day Eastern Kentucky Adventure

Daniel Boone Country Kentucky Appalachians

Want a local’s perspective on exploring Kentucky? We invited Louisville native and influencer Lauren Williams on a family getaway across her home state. Follow this local Kentuckian’s Bluegrass adventure through the Kentucky Appalachians. We’ve pulled together the full itinerary so you can experience it, too!

 

Day 1 

 

Make your way to Prestonsburg, where Lizzie B’s is serving up burgers, handhelds, tacos, pizza and their signature cactus chili. And for dessert? Your choice of over 50 milkshake flavors from Dairy Cheer.

 

Call it a night and head to Jenny Wiley State Resort Park. Here, you’ll have your choice of accommodations, including the 49-room May Lodge, 18 cottages and two campgrounds, including a boat-in site and a 121-site campground with 30- and 50-amp hookups and three travel trailer rentals. 

 

 

Photo Credit: @auren_in_louisville

Outdoors lovers will find all kinds of adventures at the park, from fishing and boating Dewey Lake to hiking and birding along miles of nature trails. Consider an elk viewing tour or mountain biking the Sugarcamp Mountain Trail if you have downtime.

 

Day 2

 

Trot your way to Pikeville for a horseback riding adventure at H&M Stables. Operated by Muddy Boots, this three-mile trail ride is perfect for all skill levels.

 

 

For a unique experience, stop in Lynch for the Portal 31 Coal Mine & Tour. Head underground and tour the mine before exploring the grounds of what was once the world’s largest coal camp. 

 

Just down the road, check into the Benham School House Inn. Tucked in the Appalachian Mountains, this charming 30-room inn was once a public school for the Benham Coal Camp. As you roam the halls, you’ll still find lockers, photos and more keepsakes from the school.

 

How about pizza for dinner? The Portal Pizzeria in Harlan offers pasta, steaks, calzones and more than a dozen wood-fired pizza options. Be sure to ask about the coal nuggets for dessert! Then, go for a nightcap at Harlan County Beer Company.

 

Day 3

 

 

Photo Credit: @lauren_in_louisville

Next up: Middlesboro. There is so much to see and do in Cumberland Gap National Historic Park. Go underground and explore Gap Cave on a guided tour. Join a park ranger and learn the history behind Hensley Settlement. Hike along more than 80 miles of trails and take in spectacular mountain views from scenic overlooks — none more mesmerizing than those seen from Pinnacle Overlook. History and nature collide in this 24,000-acre park.

 

 

Continue your adventure at Kentucky’s first state park, Pine Mountain State Resort Park in Pineville. Refuel with a Bluegrass State delicacy, the Kentucky Hot Brown, or maybe a fried catfish or chicken tender basket for lunch at Mountain View Restaurant.

 

Then, take Chain Rock Trail up to stunning mountain vistas and the storied Chained Rock. As folklore has it, this bolder was fastened to the cliff with a massive chain in 1933 to prevent it from falling on the town of Pineville below. Throughout the park, hikers can explore 12 miles of trails filled with rock formations, arches and waterfalls.

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