Best Road Trips in the USA: Kentucky

The Bluegrass State is waiting! Get your car ready, fill the tank and get on the road to discover this state's diverse beauty in this southeastern gem.

An antique map image of the state of Kentucky in the United States. This map is not to scale and is not intended for use in navigation. Joe Elberson

If you’re looking for one of the best road trips in the United States. and your travel goals include diverse discoveries for everyone in your car, then Kentucky is a must!

Dubbed the Bluegrass State, this southeastern gem is divided into four distinct regions, each bursting with delights for adventurers and music-lovers, bourbon drinkers and nature wonderers.

Today, we’ll highlight some of the most popular destinations in each of Kentucky’s four primary vacation regions and give you ideas to make your next road trip one of the most memorable and exciting yet.

Foggy morning sunrise on ranch with horses grazing Getty

Bourbon and Horse Region: Louisville, Lexington, and Fort Knox

Things to do in Louisville:

No trip to Kentucky is complete without stops at its most iconic and adored attractions. Famous for horses and bourbon, the north-central region of the Bluegrass State welcomes millions of visitors each year to partake in time-honored traditions. Spend a day at Churchill Downs, home of the legendary Kentucky Derby, and enjoy the museum and a walking tour for the price of admission. There are three meets a year where you can watch or bet on live racing and even enjoy a signature Mint Julep or Oaks Lily from any number of the racetrack’s roaming vendors. Looking for a more elevated race experience? Secure seats at an exclusive hospitality venue for complimentary gourmet food, access to private restrooms and open-all-day bars.

When your time at Churchill Downs is complete, head over to the The Kentucky Bourbon Trail Welcome Center in downtown Louisville, where you can purchase tickets to bourbon tastings and distillery tours. Mint Julep Experiences is one of several tour companies that offer guided, VIP transportation to the Bourbon Trail and back. We recommend making Louisville your home base and visiting the distilleries located east and south of Louisville by shuttle. The Saturday Bourbon Tour is a popular option that sells out quickly, stopping at Maker’s Mark, Heaven Hill and Bardstown Bourbon Company. If you’d like to book a tour on a quieter weekday, check out the Thursday Bourbon Tour, with stops at Buffalo Trace, Bulleit and Rabbit Hole.

Finally, plan a thrilling underground zip line adventure at Louisville Mega Cavern. This 2.5 hour guided adventure is appropriate for ages 7 and up and people weighing between 55 and 285 pounds. Experience the wonder of zipping across 17 miles of underground passageways, while getting an exclusive peak at what was once Louisville’s best-kept secret tucked just below the city.

Things to do in Lexington:

Lexington, home to some of the most prestigious horse farms in the nation, is just 1.5 hours by car from Louisville. For a hands-on equestrian experience, visit Stepping Stone Ranch at Deer Run Stable, where you can embark on a guided trail ride or book riding lessons. Or, visit the only park in the world that’s dedicated to man’s relationship with the horse, The Kentucky Horse Park. This attraction features daily equine presentations; three museums; carriage, horse, and pony rides; and even cross-country competitions.

If your interests veer more into the arts, make plans to visit the Trifecta Glass Arts Lounge or the Lexington Opera House while in Lexington. You’ll find that between the rolling green hills and perfectly manicured pastures there are 16 distilleries and a colorful array of restaurants. Get a sampling of everything from Southern classics to French specialties, or book a table at a unique jewelry store turned restaurant. Sports fans and first-time spectators alike tend to find that a University of Kentucky basketball game is the perfect way to round out a trip to Lexington. The Kentucky Wildcat’s men’s basketball program has eight NCAA championships and the most all-time victories of any college team, earning a special place in the fabric of true Kentucky life. 

A view of the outside of the historic Fort Knox site in Kentucky. Getty

Things to do in Fort Knox:

Before you depart Kentucky’s most-visited and historic region, stop at Fort Knox located in the Knoxville area. While no visitors are permitted inside The United States Bullion Depository at Fort Knox, which houses more than 147.3 million ounces of gold, visitors are allowed into the General George Patton Museum year-round. This historic museum provides you the opportunity to view significant military artifacts in American history and explore the life of one of our country’s most successful and unconventional military leaders.

Rural road and horse farm at sunrise in Kentucky Getty

Southern Region: Paducah, Bowling Green and Mammoth Cave

Things to do in Paducah:

Tucked in the southwestern corner of Kentucky where the Tennessee and Ohio Rivers meet, you’ll find the creative city of Paducah. This thriving arts community offers year-round performances by Market House Theatre and Paducah Symphony. If you’re a fan of folk art, check out The National Quilt Museum to see a decorative display of rotating exhibits from around the world and to take part in any number of educational workshops. Don’t leave Paducah without attending one of its touring Broadway shows or internationally renowned musical performances at The Carson Center. If you find yourself needing a few extra days to enjoy all the fun, the Paducah Main Street offers cozy lodging options, a nice variety of restaurants and unique shops.

Warren County Courthouse in Kentucky Getty

Things to do in Bowling Green:

Kentucky’s third-largest city, Bowling Green,  is jam-packed with classic American attractions and beautiful scenery. Motorheads will enjoy a day at the National Corvette Museum, where seven decades of America’s beloved sports car are on display for viewing. When you’re ready to move from racing to rocks, check out the hub of Kentucky’s Cave Country on an underground cave boat tour at Lost River Cave.. If you’re still revved for excitement after a day of caves and Corvettes, head over to Beech Bend Amusement Park. Here, you’ll discover classic and modern rides, a raceway, and even charming campsites that people of all ages have enjoyed for more than 115 years. 

Mammoth Cave walkway into the cave system Getty

Things to do in Mammoth Cave:

Just 30 minutes from Bowling Green resides the world’s largest and longest cave system, Mammoth Cave National Park. Encompassing 80 square miles, this not-to-be-missed limestone maze offers a mesmerizing variety of scenic river valleys, lush forests and plentiful wildlife. And no trip to Mammoth Cave is complete without a stop at Diamond Caverns, just six miles away. This sparkling cathedral of wonder is open year-round and offers guided tours lasting one hour. Be sure to bring a jacket, as the chilly temperatures below ground can take even summer visitors by surprise. Drive an hour east of Diamond Caverns and you’ll find yourself in the Houseboat Capital of the World at Lake Cumberland. No houseboat? No worries! Rentals are available, or you can view a fascinating range of houseboats from the Lake Cumberland State Dock Marina. The Wheelhouse, the marina’s lake-themed restaurant and bar, will welcome you with familiar comfort foods, including breakfast on the weekends.  

Country road lined with lilies and a Farm in Kentucky Getty

Northern Kentucky River Region: Ashland, Newport and Maysville

Things to do in Ashland:

Tucked on the southern banks of the Ohio River, Ashland is one of the best riverfront destinations in Kentucky. Walkable and revitalized, the four-block vicinity of Ashland’s downtown district is lined with shops, restaurants, unique art and the lush natural surroundings of Central Park. Throughout the year, you can catch a variety of concerts at Ashland’s Paramount Arts Center or enjoy arcade- and cinema-style entertainment at the Camp Landing Entertainment District.

Things to do in Newport:

Enjoy time on and with the water when you take a riverboat ride or visit one of the top-rated aquariums in the country in Newport. From Newport’s riverfront community, you can appreciate romantic views of the Cincinnati skyline, or even walk, bike or run all four of its beautifully designed bridges that connect Cincinnati and northern Kentucky. For something different, try tropical-inspired riverfront cocktails at Kon-Tiki on the Levee, or plan a quieter day of fishing and picnicking at the Port of Ashland

Things to do in Maysville:

Another scenic destination on the banks of the Ohio River is Maysville. This historic city on the boasts everything from eloquent brick buildings and a miniatures museum to picturesque recreational areas for boating, hiking and golf. Founded in the early 1800s, Maysville became an important port for the tobacco and hemp trade, as well as a significant stop on the Underground Railroad. Open at varying times throughout the year, the National Underground Railroad Museum, located within the Bierbower House, showcases important historical exhibits and artifacts that pay homage to fleeing African slaves and Kentucky’s antislavery movement.

Clark County courthouse in Kentucky Getty

Daniel Boone Region: Winchester, Cumberland and Beattyville

Things to do in Winchester:

Red River Gorge may not technically be within the city of Winchester, but it’s so close that you’ll want to make it your home base for visiting this magnificent part of the Daniel Boone National Forest. Red River Gorge is one of the most intricate canyon systems in the nation, offering an abundance of waterfalls, cliffs, rock shelters and natural bridges. With more than 500 miles of rugged trails, the gorge is one of the greatest places in Kentucky for outdoor exploration.

If you’ve ever wanted to see the Niagara of the South, then find your way to Cumberland Falls before you depart the Daniel Boone National Forest. This is the second-largest waterfall east of the Rocky Mountains, measuring 68 feet tall and 125 feet wide. Its stunning beauty and unique features are just part of the reason why more than a million people visit each year. Aesthetics aside, the falls are steeped in Native American folklore, making it an enchanting destination for admirers of rainbows and indigenous stories alike. 

If after a day of outdoor exploration you’re feeling hungry and thirsty, head on over to Winchester’s Ale-8-One store, home to Kentucky’s original soft drink, or sample some of the best beer cheese around along the one and only Beer Cheese Trail–that’s right; Winchester-Clark County is the birthplace of beer cheese! The combined comfort food and vast natural landscape of Winchester make this Kentucky city a must for your next road trip.

Things to do in Cumberland:

Cumberland is not just the Black Bear Capital of Kentucky, it’s home to Kingdom Come State Park, Kentucky’s highest state park, nestled in the crest of Pine Mountain. Take a step back in history when you view the cabins of early settlers to the area, and don’t skip the beautiful, panoramic views from Creech Overlook. This southeastern city is known as a “trail town” for its popularity with bikers and variety of outdoor fun. For those who want to enjoy the most scenic bicycle ride in the state, Cumberland hosts the Black Mountain Madness Bicycle Ride each May, which begins and ends at Kingdom Come State Park.

Things to do in Beattyville:

If you’d like to spend time in a true mountain community, stop in Beattyville while visiting the Daniel Boone Region. Here, you’re guaranteed to see an abundance of meadow and forest-based wildlife as you drive the city’s miles of tranquil country roads. You can even try your hand at some of the best muskie fishing in the world when you launch from the Beattyville Boat Ramp and float an easy .3 miles to the mouth of the Kentucky River.

Not into fishing? Book a memorable horseback ride at Beattyville’s Middle Fork Stables or Whisper Valley Riding Stables. Before you head home, be sure to do a little shopping on Main Street or catch a Beattyville festival. The Woolly Worm Festival is one of the greatest traditions in the city’s culture, as the woolly worm is believed to forecast the weather for the coming winter. Each June, another popular festival, the Beattyville Bourbon & Moonshine Festival, takes place.  During the day-long festival, you can sample spirits from across the state while listening to live music and riveting stories from third- and fourth-generation moonshiners. 

Traveling to Kentucky? AAA saves you time and money.

A road trip to the Bluegrass State is time well spent. Whether it’s historic sites you’re seeking or cave adventures or national parks that leave you wishing for more, Kentucky has a little something for everyone. Be sure to use your AAA Membership to discover discounts on hotels, car rentals and more.

Read our other Best Road Trips in the USA:

Keep reading in: