48 Hours In Prestonsburg, Kentucky

Prestonburg KY Mountain Biking

It’s no secret Kentucky is a hotspot for outdoor adventure. So it’s a good feeling to know about the state’s under-the-radar locations — the ones where foot traffic isn’t quite as heavy — before the rest of the world finds out.

Allow us to introduce you to Prestonsburg. Whether you’re chasing more technical terrain or looking for a brisk hike with a breathtaking view, this historic town will be your new, favorite hidden gem.

Prestonsburg, KY Mountains

Preston’s Station was the first town established in eastern Kentucky in 1797. Brave, adventurous men and women settled this new frontier, walking the footpaths of these mountains and paddling downstream in the waters of the Levisa Fork River. Present-day Prestonsburg — located 65 miles southeast of the Red River Gorge, 120 miles from Lexington, 136 miles from Bristol, Tennessee, and about 75 miles from Huntington, West Virginia — is a relatively new hub for hikers, bikers and paddlers, and there is plenty to explore.

Day One Options: Breakfast at Billy Ray’s

The spot in Prestonsburg for a home cooking carb-load. Open for breakfast, lunch and dinner, Billy Ray’s is known in these parts for salmon patties and meat-and-three lunch specials. Launch access point for the Levisa Fork of the Big Sandy River is located directly behind the restaurant. There is plenty of parking available and it’s free.



Sugarcamp Mountain Trails: Choose Your Own Adventure

About 20 total miles of trails begin on reclaimed mountaintop and descend into Jenny Wiley State Resort Park. The Sugarcamp Trails system officially opened to the public in July 2017. The project was more than three years in the making, made possible by a collaboration between a team of dedicated volunteers, the city of Prestonsburg and Jenny Wiley State Resort Park. It is a multi-use trail that includes a network of trails for bikers, hikers and horseback riders. It is recommended that riders are at least up to an intermediate skill level to tackle most trails on the mountain, though there are several hiking and biking routes which are accessible to all ages and skill levels. The Sugarcamp Trails website provides a map of the trail system with links to detailed descriptions, technical features and current trail conditions. Be sure to do some research before you head out so that you’re prepared. Read more about all of the adventures you can have on Sugarcamp Mountain.

Lizzie B's Cafe

Dinner at Lizzie B’s Cafe Bakery

Lizzie B’s is home of 23 Brewing Company and some of the best spinach and artichoke dip. There are healthy options like mahi mahi and salmon, or you can indulge a hamburger on a homemade bun after a day of literal running around. Homemade desserts are made daily and live local music is usually playing in the evenings. Check the restaurant’s Facebook page for the latest updates.

Live music at May Lodge

Have a drink on the patio at the state park’s May Lodge, where local bands play from 6-9 p.m. each week. Dinner is also available. If you’re staying at the lodge, then getting back to your room is an easy walk.

Kayaking in Prestonsburg

Day Two Options: Levisa Fork Paddlefest

The fourth Saturday of each month, from May to September, kayakers and canoers launch into the Levisa Fork of the Big Sandy River and make the 16.4-mile trek down river. The voyage begins at 8 a.m. in downtown Prestonsburg, behind Billy Ray’s Restaurant. Participants can bring their own kayak or canoe, or rentals are available. The scenic floating trip lasts four to six hours, depending on how fast the river is moving. Lunch is served once you reach the end of your expedition in Paintsville.

Registration is $10, which includes lunch and shuttle service from Paintsville back to your vehicle in Prestonsburg. To register, call (606) 886-1341.

Dairy Cheer

If you want a dose of east Kentucky nostalgia, stop here. Though Ashland was the original home of the Dairy Cheer, this location in Prestonsburg is one of three remaining locations. In the early 1960s, someone in the Dairy Cheer kitchen discovered how much better a burger could be if you smashed the meat down on the grill with a No. 10 bean can and the “smashburger” was born. Retro charm chasers love to stop for milkshakes and French fries, or their soup beans and cornbread — a mountain staple.

Elk In Prestonburg Kentucky

Guided Elk Tours, September-March

Jenny Wiley State Resort Park hosts guided elk tours from September through March. You can choose between a red-eye, early morning tour or go out later in the day. The elk herd was reintroduced into its native Kentucky habitat in 1997 by the Kentucky Department of Fish & Wildlife. These powerful herbivores make their home in the scenic mountains that surround Prestonsburg. Reservation price includes transportation to the viewing site and continental breakfast for morning tours. To make reservations call (606) 889-1790. Special group tours are also available.

Dinner at Pig in a Poke

Who says Kentucky don’t know ‘cue? Pig in a Poke is a Prestonsburg original, serving all the usual suspects like pulled pork, beef brisket and ribs. We all know barbecue is only as good as its sides — fresh hand-shredded cabbage for coleslaw, special recipe baked beans, and homemade batter for fried pickles.

MAC Prestonsburg, KY

Mountain Arts Center

Catch a show at the MAC. See a national musical touring act or discover your new favorite local artist. The MAC also has family friendly mountain comedy, weekly Front Porch Pickin’ open mic and is also home to Billie Jean Osborne’s Kentucky Opry. Read about Prestonsburg’s role in the Kentucky music revolution.

Where to Stay

Jenny Wiley State Resort Park

Stay in a quiet room at May Lodge or, if you prefer to sleep under the stars, campsites are also available. Campsites include electric and water, a dump station and also includes access to shower facilities and restrooms. There is a small grocery store on site. The campground opens for the season on April 1.

German Bridge Campground

German Bridge is located near the headwaters of Dewey Lake and is a prime location for horseback riders. Facilities include a 20-stall barn. Electric and water hook ups are available as well as sites for primitive camping. Shower facilities and restrooms are also available. Call (606) 874-1150 to reserve.


Brookshire Inn

Comfort Suites

Local Outfitters & Watercraft Rentals

1243 S. Lake Drive
Prestonsburg, KY 41653
(606) 886-8604

Jenny Wiley State Resort & Park
75 Theatre Court
Prestonsburg, KY 41653
(606) 889-1790

Legends Outfitters
606 Beach Road
Louisa, KY 41230

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