From the rolling green hills of Lexington’s horse country to Appalachia’s rugged mountains, Kentucky offers experiences like no other for the intrepid traveller.
As distinctive as the landscapes are the cultures you’ll find. This is a state where bluegrass mixes with honky tonk and country, where cuisine ranges from fine dining to hearty southern breakfasts (not to mention that famous fried chicken). And needless to say, you’ll be spoilt for choice when it comes to bourbon.
It can be tempting to stick to the larger towns and cities (Louisville and Lexington alone have enough to fill a week or more), but for a taste of small-town America and country Kentucky, it’s worth hiring a car and exploring the charming main street of Bardstown or venturing east into the hills where you’ll see a different side of the state and find endless opportunities for climbing, hiking, rafting and other outdoor activities. While by no means an exhaustive list, these are the spots I’d recommend adding to your route.
Louisville
This lively city might be best known as home of the Kentucky Derby – as well as seemingly endless bourbon tastings – but beyond the tourist trail you’ll find live music, secret bars and street art, all surrounded by rolling green countryside.
Save at least a couple of hours for the Muhammad Ali Center, where you’ll learn about the life and career of the legendary Louisville born-and-raised boxer, and his legacy of pursuing justice and inspiring social change. It’s a fascinating, and also very moving, experience.
The nearby Slugger Museum, which teaches you everything you need to know about baseball bats, is surprisingly fun, even if you have no interest in the sport. On a sunny day, take a walk through Cave Hill Cemetery, where you’ll find Muhammed Ali’s grave (Colonel Harland Sanders is also buried here if you want to pay homage to the king of fried chicken).
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But back to bourbon. There are six distilleries all within five minutes’ walk of one another in the Bourbon District – Angel’s Envy is a favourite of mine – and tastings, speakeasies and bars abound. For a truly special bourbon experience, Heritage Farm takes the crown. Here you can enjoy a tasting in one of the most beautiful horse barns in the state and meet some of the much-loved retired racehorses while enjoying an old fashioned or two. This is picture-perfect Kentucky – we’re talking red barns, green hills and white fences.
No matter how you feel about horse racing, Churchill Downs is worth a visit to understand the phenomenon that is the Kentucky Derby. Beyond touring the impressive grounds themselves, there are also exhibits on past winners, how Derby Day is put together, and the African American experience in horse racing.
For bedding down at night, the Omni hotel has a great central location, but for a full bourbon experience I’d recommend Hotel Distil. Meanwhile, the wonderful Trouble Bar has now been turned into a bookstore/coffee shop – you’ll find the same revolutionary energy, but now powered by caffeine rather than booze.
Lexington
Lexington is Louisville’s younger (and possibly slightly cooler) sister. Check in for a couple of nights at the beautifully designed Manchester Hotel, which is an ode to the racehorse. Both the ground floor and rooftop bars are perfect spots to enjoy a cocktail or glass of wine, plus there’s an incredibly chic gym. Of course, bourbon is a big deal here, too. There are a number of distilleries in the city itself – including Barrel House Distilling Co., Bluegrass Distillers and James E. Pepper Distillery – as well as plenty in the surrounding countryside. Visits and tastings can be arranged as part of a tour or with the distillery directly, but do book ahead as spots fill up fast.
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There are plenty of lively restaurants and bars in the Distillery District – the Burl Arcade and Crank & Boom Ice Cream lounge are top choices – but it would be a mistake to miss the small plates at Epping’s on Eastside. Just across the street is glass art studio and fine art gallery Trifecta, which is also home to a speakeasy with a lounge and outdoor seating, where you can have a drink while watching the impressive art of glass blowing. Any bourbon cocktail you order here will be memorable, but I’d recommend trying the Paper Plane, which also contains Aperol, Amaro Nonino and lemon.
Lexington also does coffee well; Common Grounds and Java Jukebox are two of my favourite spots to grab a brew – make sure you try one of the grilled cheeses at the latter.
Bardstown
While Louisville and Lexington are top destinations for bourbon, ultimately it’s Bardstown that takes the crown. This charming little town has 11 distilleries within a 16-mile radius – including the popular Bardstown Bourbon Company, as well as Jim Beam, Heaven Hill and Log Still – and wherever you step you’ll find bars, tastings and fun bourbon experiences.
But you don’t have to love bourbon to love Bardstown. This is quintessential small-town America. There are a slew of fun, boutique hotels, including the Motor Lodge which can be found on the road leading into town, as well as Distill-Inn, Talbot Inn, and former 19th-century jailhouse The Jailer’s Inn, which are all downtown.
For a big southern breakfast, head to Mammy’s, where you’ll find huge pancakes, Kentucky’s famous Hot Brown (turkey and ham piled on toast), and the friendliest service. The doughnuts at Hadorn’s Bakery are legendary in Kentucky, while Big Wally’s serves ice cream and soda floats that will satisfy any sweet tooth.
Glasgow
The main tourist draw of this region is the impressive Mammoth Caves, but base yourself in the nearby town of Glasgow for a classic American small-town experience. Copper and Elk is a gorgeous, huge apartment right on the main square that can be booked on Airbnb. The local owners also have the Plaid Peacock interconnecting apartment, which I’ve not stayed at but have confidence in the quality. Also on the main square is the bustling Hive cafe with excellent coffee, while Fine Arts Bistro is a top recommendation for breakfast, with some great vegetarian options (which is not always easy to find in Kentucky).
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Make sure you save some time to browse Off the Square and the Nadine West Book Co, which are both locally owned businesses and very welcoming. The Plaza Theater, which you’ll spot at the south end of the square is a historic spot where performances and community events are held throughout the year.
Cave tours at Mammoth do get busy so it’s a good idea to book ahead. Across the south, you’ll often hear counties boasting they have the best caves, but Mammoth really does have a legitimate claim here – it’s home to the longest-known cave system in the world. To the south of Glasgow (a roughly 30-minute drive) at Barren River Lake State Resort park you can also hike, hire a canoe or boat, and play a round of golf, and there is a rustic lodge with rooms and cabins if you’re keen to stay out in nature.
Red River Gorge
Under two hours from Louisville and a mere hour’s drive from Lexington you can find yourself deep in some of Kentucky’s most stunning nature. Red River Gorge is located in the Daniel Boone National Forest, which has long been popular with climbers and is fast becoming a desired destination for anyone who loves the outdoors. There are a few pleasant locally owned spots to base yourself in – Blackbird Cabin, which can be booked on Vrbo is a good choice – or you can immerse yourself in nature at Canopy Crew Treehouses and Cliffhouses.
For camping, secure yourself a spot at Miguel’s. A Red River institution, Miguel’s Pizza has been serving delicious hot pies loaded with toppings since 1986. The surrounding campsite is a particular draw for climbers keen to explore the area, and the store is quite literally filled to the rafters with clothing and equipment. Other top spots for food include Redpoint BBQ and Red River Rockhouse, which serve classic American fare.
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If you’re planning on climbing, Southeast Mountain Guides will help you plan the perfect trip, and also have a Via Ferrata that takes you around the cliff face and under a waterfall – it’s terrifying and thrilling in equal measure. The Gorge Underground offers a kayaking experience like none other. Kitted out with helmets and head torches you explore a flooded underground limestone mine, which has been prettily lit up. For a mud-soaked rip-roaring ride, the staff at Red River Gorge Off-Road UTV Tours know how to have a good time, following trails that thunder through creeks, up hills and along mountainsides.
Corbin
For a taste of Appalachia without having to head deep into hill country, spend a day in Corbin, a small town nestled in the foothills of the mountains. The town holds the rather dubious accolade of being the home of the first ever KFC, and at the Harland Sanders Cafe and Museum you can learn about the (surprisingly chequered) past of the Colonel himself, as well as how KFC became the phenomenon it is.
There’s also a pinball museum, axe-throwing, several quirky little stores and boutiques, and some great spots to eat. Folktale is a very pleasant for coffee and pastries, while Wrigley’s Taproom should be your first port of call for beers or bourbon. Corbin sits on the doorstep of some of the most accessible hiking, rafting, climbing and horse riding in the state. You’re right next to Daniel Boone Forest, and just a 30-minute drive from the impressive Cumberland Falls.
Pikeville
Tucked in the northern corner of Kentucky right on the border with Virginia and West Virginia is Pike county, centred around the town of Pikeville. Thanks to its university and medical centre, Pikeville has thrived in recent years (while other eastern Kentucky towns have sadly struggled with poverty and unemployment), and there is plenty to do and see, especially if you love country music. Pikeville is on Kentucky’s Country Music Highway, which is a road trip that takes you through key points in a region that has produced the likes of Loretta Lynn, Chris Stapleton, Billy Ray Cyrus, Tom T Hall, Dwight Yoakam and Patty Loveless – to name just a few.
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Pikeville is also the home of the legendary blood-filled Hatfield–McCoy Feud that started over a hog in 1878 and raged for decades between the two families, resulting in murder, bloody brawls and bitterness. It’s a real lesson on not holding a grudge. At Chirico’s Ristorante you can enjoy pizza, pasta and calzones in the building that Randolph McCoy (head of the McCoy clan) last called home. Ask the staff to show you the upstairs which is largely unchanged since McCoy lived there.
Country music fans might want to make the pilgrimage to the former family home of Loretta Lynn, the coal miner’s daughter, in Butch Hollow, just 45 minutes outside of Pikeville. Just note, it’s worth calling ahead and arranging a tour, which starts at the Grocery Store. You can make the drive alone, but the road is narrow and the area has an interesting vibe, to say the least – my car was pursued by two furious barking guard dogs for a good 200 metres.
My top tip for Pikeville: stop in and visit Tony and Jay from the Welcome Center out by Hardee’s as soon as you arrive – their remarkable knowledge and enthusiasm for the area will give you more than enough ideas on how to spend your time in the county. The nearby town of Paintsville is quieter, but worth a wander – and make sure you stop in at The Coffee Shop for a brew.
Getting there
Airlines including British Airways, Delta, American Airlines and Virgin Atlantic fly to Louisville with one stop, often in Atlanta, Chicago or Charlotte. Flight time is usually somewhere between 12 and 14 hours. Alternatively, fly direct with British Airways to Nashville, which is just across the border from Kentucky in Tennessee, and rent a car.
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