Outdoor Adventure and Music History: Family Activities in Eastern Kentucky

Kentucky Appalachians

By: Abby R. Stewart

Updated: July 26, 2024

If you’re looking for a getaway filled with everything from outdoor recreation to theater and music, a trip to Eastern Kentucky is just what you need. With so many different and thrilling things to do and see, a getaway to the Bluegrass State will surely be filled with fun for your whole family—without breaking the bank, while you’re at it. Whether you’re looking for an exciting adventure, a relaxing retreat, a cultural experience or a combination of it all, an Eastern Kentucky vacation will deliver!

The Zip, Paddle & Saddle Package

Are you and your kids an adventurous bunch, always looking for something new to try? Well, if you and your gang are the energetic types, the Zip, Paddle & Saddle Package in Pike County is your one-way ticket to an unforgettable good time. Each season offers extraordinary scenic views to enjoy while trying your hand at these exciting adventures.

Natural Bridge Resort State Park

Tap into nature at Natural Bridge Resort State Park, where you can escape the hustle and bustle of busy day-to-day life, slow down a bit and spend some quality time with each other in the beautiful great outdoors. Surrounded by the Daniel Boone National Forest, the natural bridge stands 65 feet tall, spans more than 78 feet and is one of the largest natural bridges in the area. Families love to partake in all sorts of activities while visiting the park: fishing, canoeing and paddling on the lake are among some favorites, but taking the trail up to the natural bridge itself has always been the most exciting and rewarding. You can also take the sky lift, which goes all the way up to the top, and then walk across the bridge to soak up the unparalleled 360-degree views of the surrounding majestic Kentucky scenery. A breathtaking forest goes on for miles, marked by towering sandstone cliffs and a beautiful lake—a picturesque scene you have to see to believe.

Natural Bridge Resort State Park is the perfect destination in Eastern Kentucky to get outside and experience the beauty and recreational opportunities Mother Nature has to offer. If you want to try something different, join in on some Appalachian square dancing, a popular tradition at Natural Bridge for the past 45 years. It is truly an unforgettable experience.

Jenny Wiley Theater

One of the most rewarding ways to travel is to experience the culture and spirit of the place you’re visiting. At Jenny Wiley Theater, you can find the heart of Eastern Kentucky on display for you and your family to enjoy.

A popular among many is Mary Poppins, performed by an amazing selection of local talent. Supplementing the creative experience provided by the many cultural arts opportunities in Eastern Kentucky, a trip to the Jenny Wiley Theater in Jenny Wiley State Resort Park, in Prestonsburg, is sure to please! Adding to the fun, they now have a year-round 200-seat indoor Mainstage Theater in downtown Pikeville to enjoy, too. With productions dating back to 1964, the Jenny Wiley Theater is a long-running tradition for families, both visiting and local. You won’t want to miss the opportunity to experience it for yourself during your vacation.

The Country Music Highway

Nothing spells good old-fashioned family fun like a road trip, and The Country Music Highway that runs north and south through Eastern Kentucky is not your average highway. Encompassed by tall mountain ridges, panoramic scenic countryside and an abundance of natural beauty, this hidden treasure provides visitors the chance to enjoy music, crafts, dining, sightseeing and adventure all along the route. Named for the many country music stars who call the region home—such as Loretta Lynn, Wynonna and Naomi Judd, Billy Ray Cyrus, Dwight Yoakam, Patty Loveless and more—Highway 23, fondly referred to as the Country Music Highway, runs right through their old stomping grounds.

Steeped in rich music history, the region surrounding the Country Music Highway provides visitors with ample opportunities to hear live music at a variety of venues, such as an outdoor amphitheater and the historic Paramount Arts Center in Ashland, to name a couple. Countless shows and family-friendly festivals showcase the talent of the region as visitors can enjoy great music, amazing natural scenery and recreation opportunities all along the highway.
Unparalleled live entertainment, a sharing of rich culture, exciting outdoor adventures and a lush landscape that can be enjoyed from just about any vantage point; these are the things families from all over have come to know and love about vacationing in Eastern Kentucky. We invite you to use this list to construct your own version of a memorable Eastern Kentucky vacation, marked by a cost-effective yet enriching experience you’ll be talking about for years to come.