Skip to Content

Kentucky Road Trip: 9 Exciting Cities to Explore

Kentucky Road Trip: 9 Exciting Cities to Explore

Kentucky, often renowned for its rolling hills of bluegrass and spirited thoroughbreds, is a state that extends an invitation to the roads less traveled, where every mile is rich with tradition and the warmth of Southern hospitality. Whether you’re a seasoned road-tripper searching for new horizons or a curious traveler with an itch for small-town charm, these nine Kentucky road trips are your ticket to discovering America’s heart and soul.



Begin your journey in Frankfort, Kentucky’s capital city, nestled between the banks of the Kentucky River. History whispers through the town, beginning at Rebecca Ruth Chocolates, a renowned candy factory. A few of their most popular fresh gourmet items are Kentucky creamed pull candy, bourbon balls, and pecan turtles.


The stately Kentucky State Capitol beckons admirers of grand architecture and a 34-acre setting along the Kentucky River.  It is one of the 11 capitol buildings worked on by the Olmsted Brothers firm and resembles the Capitol Building in Washington DC.

Do some shopping in the charming downtown area, admire the murals and street flags (shout out to Will Chase, one of our Broadway faves), and then finish your Frankfort trip on the Kentucky Bourbon Trail with a Buffalo Trace tour. This historic facility has been satisfying customers for 200+ years.



Venture next into Lexington, the Horse Capital of the World, where equestrian dreams prance in every paddock. At Keeneland Racecourse, feel the hoof beats echo beneath the mint julep skies. I fondly remember meeting my in-laws there for the first time.


Next, visit the Kentucky Horse Park, one of the most fascinating animal encounters ever. You will surely develop a love for this esteemed equine after learning about their breeding, racing, and history.


If you are a history lover, check out the Mary Todd Lincoln House, Honest Abe’s beloved wife, and tour Ashland, the Henry Clay Estate. There are several tour options, and you can’t go wrong with any of them.

Pro Tip: Check out the Abraham Lincoln mural by Kobra, one of the world’s most fantastic muralists.



Onward to Louisville, a city that’s a cocktail of urban vibrancy and traditional Southern soul. The whole family will love the legendary Louisville Slugger Museum & Factory, which celebrates America’s pastime.


Louisville’s main attraction is Churchill Downs Racetrack, where the annual Kentucky Derby race occurs. Tour the horse track and museum, and learn some cool facts about America’s “Run for the Roses.” And you can’t come to town without trying the Kentucky state dish, the Hot Brown, made famous at the historic Brown Hotel in Louisville.

You’ll find a few KY Bourbon Trail sites here, as well, such as Angel’s Envy, Old Forester, and Evan Williams.

Pro Tip: Experience the country’s only underground zip-lining at Mega Caverns.


Grand Rivers

Discover the small but mighty Grand Rivers in the heart between the lakes. The tranquil waters of Kentucky Lake and Lake Barkley offer a serene escape, ideal for fishing or a sunset sail.


Sample the legendary pies and gourmet pork chops at Patti’s 1880s Settlement, where Southern cuisine and ambiance unite the past and present. I could shop and browse for hours at this treasure trove, spread across a 45+-year-old recreated historical log cabin village.



Elizabethtown, affectionately known as E-town, delivers an unforgettable slice of Americana. Marvel at the vintage cars from the early 1900s to the 1960s at Swope’s Cars of Yesteryear Museum or meander through Freeman Lake Park to embrace nature’s simplicity and beauty.

E-town’s cordiality is famous, with locally owned shops and eateries offering treasures and treats in equal measure. By the way, this is the birthplace of bourbon, but I prefer coffee drinks from Vibe Coffee.


Bowling Green

Bowling Green rolls out the red carpet for car fans at the National Corvette Museum, capturing the spirit of America’s sports car. The name Bowling Green is nearly synonymous with the Corvette Museum.

Meanwhile, Lost River Cave provides an underground experience, uniting geology and history and luring explorers into the cavernous wonders beneath. Enjoy 2 1/2 miles of nature trails and 72 park acres, as well as the cave system, butterfly habitat, and gem mining.

Bowling Green is also a fast-food capital, with 200+ restaurants to choose from, many offering full sit-down service.



In Clermont lies a sanctuary for bourbon lovers and the world-renowned Jim Beam Distillery. It’s in these aging barrels that 200+ year-old stories and spirits are delicately crafted with the same care as fine poetry.


One of the coolest offerings in Kentucky is found here, the Bernheim Arboretum & Research Forest, where forest giants (constructed from recycled wood from the region) reign supreme and forty miles of trails await you. Normal hours are 7 AM to 5 PM; expect hours of wait time entering the forest when the weather is favorable.

Photo from Bernheim IG page.


Newport is a gem on the Ohio River, shining brightly with entertainment and nightlife. The Newport Aquarium brings you face-to-fin with aquatic wonders, sparking both awe and inspiration.


Retail therapy at the Historic District and Newport on the Levee adds a playful note to the city’s laid-back elegance. Grab a perfect lunch of tomato soup and grilled cheese sandwiches at Tom + Chee, then ride on the Ohio River on the Belle of Cincinnati riverboat, the flagship of BB Riverboats.


Mammoth Cave

Conclude this wonderful Kentucky road trip in Mammoth Cave. Mammoth Cave National Park offers a natural world wonder like no other. The vast underground labyrinth invites national parkgoers to ponder the earth’s mysteries.


Besides the caves, the stately property offers biking, canoeing, hiking, and horseback riding opportunities. It also boasts the proud ” UNESCO World Heritage Site and International Biosphere Reserve” title.

Make reservations; cave tours fill up quickly. There are fees for the cave tours and camping, but otherwise, this park is free to roam around in.


Embark on this extraordinary Kentucky road trip and savor the different cadences of life within these nine cities. Travel enthusiasts, pack your bags and set your soul to roam—you’re about to ride through the scenic backroads of the Bluegrass State.

Happy travels, and may Kentucky’s roads rise to meet you!

This site uses Akismet to reduce spam. Learn how your comment data is processed.