Your Fireside Fortune Itinerary: Experience the Ultimate Kentucky Road Trip!

Photo Credit: Corey Woosley



Stunning natural beauty above ground and below. Bucket list adventures to thrill kids and adults. And some of the most unusual lodgings you’re bound to find anywhere. 

That’s right—Kentucky is the perfect playground for a family-friendly road trip! 

Delve into the darkest underground caves and climb into the canopy of Kentucky’s lush forests on a road trip like no other! Want to learn more? Follow along with the Simmons family as they complete the same voyage on Kentucky’s Original Series, Fireside Fortune!

Central Kentucky: Bluegrass, Horses, Bourbon & Boone Region

Start your road trip in Central Kentucky—the horse capital of the world and the heart of bourbon country. Your home for the night is the Queenslake Bed & Breakfast, a stunning mansion and horse farm in Georgetown. With only three guest rooms, you’ll feel like a lord or lady of the manor during your stay. 

Schedule a guided trail ride or lesson mounted atop one of their graceful horses—it’s the best way to discover the 40-acre private lake and serene forests on the property. 

See more with Rail Explorers, a unique way to traverse the Bluegrass countryside. You’ll hop on a four-wheeled rail bike and pedal your way across the tracks of the Louisville Southern Railroad. (Don’t worry about trains—Rail Explorers works closely with the railroads to ensure open track during your ride.) 

The 2-seat or 4-seat bikes are equipped with custom electric motors, so you won’t have to work too hard while you take in spectacular views of rolling fields, roaming horses, and the stunning Kentucky landscape. 

At the end of the day, head back to Queenslake to sip a rich local bourbon on the mansion’s front porch. 

Northern Kentucky River Region

Rise above it all at EarthJOY Village, a one-of-a-kind accommodation in Germantown. Choose from three different tree houses perched high above the ground, each comfortably fitted out with real beds and kitchenettes. Despite the cozy interiors, you won’t forget you’re in the trees, thanks to the big windows and leafy views. Lounge in a hammock or Adirondack chair and soak up the scene, or hike over 20 miles of trails on the property. 

You can also add a tree-climbing adventure to your stay. You’ll be cinched into a harness and taught to ascend high into the trees on rope lines. Step out onto the branches of a towering American Beech and hang upside down…if you dare.

Rolling a barrel at the Baker-Bird Winery and B.Bird Distillery in Augusta. Photo Credit: Chris Woosley.

Back on solid ground, reward yourself with a well-earned trip to Baker-Bird Winery and B.Bird Distillery in Augusta. This is the oldest and largest wine cellar in America, dating back to 1850. The distillery goes back even further, first opened in 1797 by a Revolutionary War veteran. Book a tour and tasting to step into the cavernous stone cellar, where you can sample wines like sweet vidal blanc and dry cab franc. 

Daniel Boone Country Region

Some of Kentucky’s most stunning natural wonders can be found in Daniel Boone Country. Discover a unique geological formation in Daniel Boone National Forest—massive stone arches created over millennia by wind and water erosion. Spot four of them on the 3.5-hour guided Waterfalls and Arches Tour, along with the Bark Camp Creek Cascades and Amos Falls hidden within the forest. 

For a waterfall with a little more splash, take the Rainbow Mist Ride to Cumberland Falls. Climb aboard an inflatable raft and let your guide paddle you to the base of the falls, where you can soak up the majesty—and the mist—under the 68’ cascade. 

After your adventure, mosey to your personal Old West-style covered wagon for the night. The Conestoga Wagons at Sheltowee Trace Adventure Resort are arranged in a traditional wagon circle around a fire pit. Inside, they’ve been upgraded with comfortable beds and electricity, including heat and air conditioning. The pioneers would be so jealous! 

South Central Kentucky: Southern Kentucky Vacations Region

South Central Kentucky is all about life on the water. Wolf Creek National Fish Hatchery supports local fish populations, raising 275,000 pounds of rainbow, brook, brown, and cutthroat trout per year. You can learn about the trout life cycle, feed the fish in the outdoor raceways, and fish in the pristine Hatchery Creek habitat. 

The twins make a splash with the houseboat’s slide. Photo Credit: Chris Woosley.

Take your fishing adventure further with a Lake Cumberland Fishing Charter. Your captain is a Lake Cumberland expert and a striper fishing pro. He’ll provide rods and tackle and guide you to the best fishing spots for striped bass catches. They even filet and clean your fish for you! All you need to provide is a Kentucky fishing license, available online. (Kids under 16 are exempt from licensing requirements.) 

Bring your catch with you to your home for the night—a floating paradise from Lake Cumberland Houseboat Rental. Houseboats range from cozy to sprawling, perfect for a couple or a full family reunion. Plus, you can’t visit the “Houseboat Capital of the World,” and NOT stay in one! In the morning, hurtle down the houseboat water slide right into the lake. It will wake you up better than a cup of coffee.  

Caves, Lakes & Corvettes Region

You’ve been up in the trees and on the water. Now it’s time to go underground in Horse Cave with a Hidden River Cave Tour. This one-hour tour will lead you deep underground to a subterranean river snaking through the caves. Cross a 100-foot-long suspension bridge (the world’s longest in-cave swinging bridge!) to reach Sunset Dome, an enormous 10-story cavern that has been naturally “painted” in the peaches and pinks of a beautiful sunset. 

Checking out the Sunset Dome. Photo Credit: Chris Woosley.

Then, prepare to get dirty at Blue Holler Offroad Park. Rent one of their ATVs (or bring your own) and kick it into gear through creeks, across boulders, and up jumps. Look for caves and a waterfall on the property while you’re driving. If you don’t come back muddy, you’re doing it wrong! 

Spend the night in Bowling Green. Stay in one of the city’s historic hotels, from charming B&Bs to luxury escapes. After you’ve hosed off the mud, head out into the town to visit breweries, vineyards, and bourbon bars. And don’t miss the National Corvette Museum—it’s home to over 70 new and classic cars. 

Western Waterlands Region

Kentucky’s Western Waterlands Region is an outdoor paradise. Rent a canoe or kayak on Kentucky Lake and paddle across the sparkling surface, taking in the wildlife along the way. Jet skis, pedal boats, pontoons, and fishing boats are also available from multiple vendors, so you can lake however you like. 

For a closer look at the local wildlife, head to Woodlands Nature Station. Sandwiched in the narrow spur between Kentucky Lake and Lake Barkley, you can meet rescued animals like coyotes, a bobcat, bald eagles, and a parliament of owls. Drive through the Elk & Bison Prairie to spot majestic giants as they graze and gaze! 

You could spend your whole day at Pennyrile Forest State Resort Park, canoeing across the lake, hiking miles of natural trails, or fishing from the dam. There’s even a full golf course here under lush shade trees. When you’re worn out, set up a rustic campsite for an evening under the Kentucky stars. Or sleep in style at Kentucky Lake Glamping, where you can choose from charming vintage campers, cozy tiny homes, and a sleek geodesic dome with two queen beds, a kitchenette, and a clear view across the campground.

The Bluegrass State Awaits! 

From climbing in a canopy of trees to exploring caves, glamping and kayaking, Kentucky is home to a world of exciting outdoor adventures. Whether you’re following the route of the Simmons family in Fireside Fortune or planning your own road trip, expect to find a diverse range of experiences throughout the Bluegrass State!

Enjoying our content?

Subscribe and receive a weekly newsletter packed with awesome stories to inspire you!

Related articles

Weird and Wonderful Kansas Attractions

From wild Wizard of Oz-themed attractions to mushroom-shaped rock...

Journey Through History: 6 Must-Visit Spots on Alabama’s Civil Rights Trail

Home to museums, interpretative centers, monuments and more, the...

Love Lobster Rolls? Dig in at These Popular New England Joints!

Are you ready to feast? Check out these mouthwatering...

Sips and Sights: 10 Rooftop Bars in Nashville

Looking for cocktails with a view of the Nashville...

Hill Country Hopping: Three Days from San Antonio to Austin

Only 80 miles separate downtown San Antonio from downtown...

Popular experiences

Oregon Road Trip Series: Columbia River Gorge and Mt. Hood

The second stop on our Oregon Road Trip series...

Oregon Road Trip Series: Columbia River Gorge and Mt. Hood

The second stop on our Oregon Road Trip series...

10 of Colorado’s Best-Kept Secrets

Think “Colorado” and what likely comes to mind is...

Three Days of Family Fun in Boone, North Carolina

If you're seeking a long weekend getaway with your...

Discover St. John’s Shopping Scene in the U.S. Virgin Islands

If you’re looking for retail therapy in between the...

Why People Get Padre Island and South Padre Island Wrong

You've seen people say it on your social media...