The Best Things to Do in Kentucky: Bourbon, Bluegrass and Beyond

Ask most British travellers what they know about Kentucky and you will get three answers: bourbon, horses and fried chicken. All true, all worth the flight. But spend a fortnight driving the Bluegrass State and you discover the world’s longest cave system, the hometown of Muhammad Ali, a music tradition that gave the whole region its nickname, and small towns where the welcome is as warm as the whiskey. Here are the things to do in Kentucky that make it the most underrated road trip in America.

1. Follow the Kentucky Bourbon Trail

Start with the obvious, because it is obvious for a reason. Around 95% of the world’s bourbon is made here, and the distilleries strung between Louisville, Bardstown and Lexington are the finest collection of their kind anywhere. Maker’s Mark lets you hand-dip your own bottle in red wax; Woodford Reserve sits among thoroughbred farms with copper pot stills and stone warehouses from the 1800s; Wild Turkey pours big and bold above the Kentucky River. Do two a day at most, book the famous names ahead, and let the drives between them (past white fences and tobacco barns) be part of the pleasure.

2. Walk Louisville’s Whiskey Row

Louisville is where bourbon barrels once lined the Ohio riverfront, and Whiskey Row has roared back to life: Evan Williams, Old Forester, Michter’s and Angel’s Envy all have showpiece distilleries within a few blocks of each other, with cocktail bars and restaurants filling the gaps. Stay downtown and you can walk to all of it. Try a Hot Brown while you are here, the open-faced turkey sandwich invented at the Brown Hotel in 1926 and still Louisville’s signature dish.

3. See the home of the Kentucky Derby

Churchill Downs and its famous twin spires have hosted the Kentucky Derby every year since 1875, making it the longest continuously held sporting event in America. Even outside race days the Kentucky Derby Museum is superb: a 360-degree film that puts you trackside, a walk through the historic grandstand, and the chance to meet a retired thoroughbred or two. Time your trip for spring and you might catch live racing.

4. Meet the horses in Lexington’s bluegrass country

The rolling pastures around Lexington are home to some of the most valuable horses on earth, and the region calls itself the Horse Capital of the World with a straight face. Tour a working stud farm to see foals and stallions up close, or spend a morning at the Kentucky Horse Park, where dozens of breeds live alongside a museum of the horse. The scenery, all limestone walls and impossibly green fields, is reason enough to come.

5. Go underground at Mammoth Cave

Beneath the hills of south-central Kentucky lies Mammoth Cave, the longest known cave system in the world with more than 400 miles mapped so far. It is a UNESCO World Heritage Site and a US National Park, and the ranger-led tours range from gentle strolls through cathedral-sized chambers to crawls for the adventurous. Above ground, the park’s forests and rivers make for a peaceful afternoon after the darkness. Car enthusiasts should carry on south to Bowling Green, where the National Corvette Museum sits beside the only factory in the world that builds them.

6. Stand in Muhammad Ali’s corner

Louisville is the birthplace of the Greatest, and the Muhammad Ali Center on the riverfront is one of the most moving museums in the South. It tells the whole story: the boxing, yes, but also the activism, the faith and the humour that made Ali a global figure. Round off a sporting afternoon at the Louisville Slugger Museum a few streets away, where the world’s biggest baseball bat leans against the factory that has made them since 1884.

7. Hear bluegrass where it was born

Bluegrass music takes its name from Bill Monroe’s Blue Grass Boys, and Monroe was a Kentucky boy through and through. Owensboro, on the Ohio River, is the official bluegrass capital and home to the Bluegrass Music Hall of Fame and Museum, with live jams most weeks. Across the state you will find pickers on porches, in barns and in bars, and if you are on a wider Southern road trip, the Smoky Mountains and Nashville are within easy reach for the full musical picture.

8. Slow down in Bardstown

Officially the Bourbon Capital of the World and unofficially one of America’s prettiest small towns, Bardstown is brick storefronts, church spires and front-porch friendliness. Heaven Hill, Willett and Jim Beam distilleries are on its doorstep, the bourbon bars are excellent, and every September the town hosts the Kentucky Bourbon Festival during Bourbon Heritage Month. Base yourself here for a few nights and the Bourbon Trail comes to you.

9. Find the real Colonel Sanders

Yes, that Colonel. Harland Sanders perfected his fried chicken at a roadside café in Corbin, in the hills of south-eastern Kentucky, and the original restaurant is now the Harland Sanders Café and Museum, restored to its 1940s glory. It is a charming stop just south of Lexington, and the chicken is, naturally, very good. While you are there, Cumberland Falls is a short drive away: the largest waterfall in the South, famous for the moonbow that appears over the water on clear full-moon nights.

10. Get out into the Red River Gorge

For hikers, Kentucky’s best-kept secret is the Red River Gorge in the Daniel Boone National Forest: more than a hundred natural sandstone arches, sheer cliffs and forest trails an hour east of Lexington. Natural Bridge State Resort Park is the easy way in, with a sky lift to the top of a 78-foot arch and views across the whole gorge. In October the trees turn every shade of amber, which feels appropriate for the state that ages its whiskey in oak.

Ready to see it for yourself?

Everything here fits into one tailor-made trip, and we have built Kentucky holidays for every appetite: a 5-night Louisville city break, an 11-night bourbon road trip, a 14-night tour of the state’s legends and landmarks, and longer routes that pair Kentucky with Nashville, the Smoky Mountains and the Deep South. Every one comes with flights, hand-picked hotels and the experiences that make Kentucky Kentucky, with prices from £1,269 per person. Explore the full collection on our Kentucky holidays page, and let our USA specialists tailor the route around you.