Famous for folk music, smooth liquor and handsome horses, the small towns of the Bluegrass State are blessed with immense Southern charm, golden bourbon and green vistas. Miles of trails crisscross Kentucky, stringing together plenty of picturesque little towns and attractions that can be visited in one trip. Designated 'trail towns' are dotted along historic or cultural routes where you’re sure to find guides, lodgings and a hearty meal along the way.
Read on for our pick of the best charming small towns in Kentucky...
Full of quaint old town charm, Paducah is sited at West Kentucky’s Four Rivers Basin making it a great place to board a traditional steamboat cruise or follow the marked River Walk trail. It’s also an epicentre for folk arts and crafts with vintage shops, pretty cottage stores and such a strong quilting tradition that there’s a space – the National Quilt Museum – devoted to it. Paducah’s farmers' market is the perfect place to browse the region’s finest produce and immerse yourself in the local community.
For a taste of eastern Kentucky’s Appalachian mountains, the hip town of Whitesburg on the edge of the coalfields is ideal. Here you’ll find the Appalshop arts centre hosting live theatre, folk music and movie nights, alongside vintage record stores, eateries and bars serving up freshly cooked meals and distilleries such as Kentucky Mist Moonshine offering whiskey-tasting and tours. Head to Falcon Overlook for a stunning overview of the surrounding scenery.
A quintessential Kentucky town at the heart of the state, Georgetown has bluegrass, bourbon and horses in spades. Not only does it lay claim to being the birthplace of bourbon but it’s also near the centre of horse country, where you can visit Kentucky Horse Park and meet racing stars at Old Friends Thoroughbred Retirement Farm. The town is a hub for fairs and festivals including antiques markets and the International Kite and Culture festival, where you’re sure to catch a local bluegrass band.
Visitors curious about the Appalachians and keen on outdoor adventure will love this gem of a trail town in eastern Kentucky. It's long been established as the gateway to the Breaks Interstate Park. Frontiersman Daniel Boone is said to have taken his first steps into modern Kentucky here, on a hunting expedition in 1767. Perched on the edge of the Big Sandy River and the Pine Mountain State Scenic Trail, the small arty settlement is the perfect base for wild hiking and white water rafting.
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The aptly-named Kentucky town of Midway sits in the centre of the state, and is right in the middle of horse country, making it the ideal spot to experience Kentucky’s rich thoroughbred history. Gorgeous stud farms dot the area including the nationally renowned Airdrie Stud, Three Chimneys and Lane's End Farm. The pretty town is also a hub for boutique shops and restaurants with some of the finest dining in central Kentucky.
The folk arts and crafts capital of Kentucky, the pretty trail town of Berea is full of homegrown charm. Browse the historic artisan village and watch out for ‘Studio Artists at Berea’ signs to see artists working at crafts from jewellery to instrument-making. Kentucky Artisan Center houses locally-produced collections, while fascinating workshops such as Weston Glass Studio are open to visitors. Boone Tavern Hotel, which dates back to 1909, is perfect for an overnight stop.
Kentucky’s first self-styled urban trail town, Elizabethtown sits to the south of Louisville and offers plenty of attractions including the Hardin County History Museum, Historic State Theater, a vintage car museum and retro shopping arcades in downtown. Kentucky’s Bourbon Trail is also known for its craft beer, and visitors can sample a Trail Town Ale at Flywheel Brewing. It's also an ideal base for hiking, biking and paddling adventures in the local lakes and parks.
Danville embodies original Kentucky – it was the first state capital and also where its constitution was signed in 1792. Visitors can still tour the historic buildings at Constitution Square (pictured) to learn about its history. At Kentucky's geographical and historic centre, the state’s first courthouse, college and law school were all established here. The arts have a strong presence too, and the former federal building in downtown has recently been transformed into the GLASS National Art Museum.
As Kentucky’s second oldest city dating back to 1780, Bardstown is brimful of historic charm and is a must-visit on any trip to the state. It boasts 200 buildings on the US National Register of Historic Places including the quaint Old Talbott Tavern (pictured). As the self-styled Bourbon Capital of the World, it sits at the beginning of the official Kentucky Bourbon Trail so it’s a great place to sample the famous amber nectar, with 11 craft distilleries dotted within 16 miles (26km) of downtown.
The historic hamlet of Rabbit Hash on the Ohio River is a small but perfectly formed microcosm of Americana, named on the US National Register of Historic Places for its old tumbledown wooden buildings dating back more than 200 years. One of the most atmospheric is the Rabbit Hash General Store (pictured), generally considered the oldest example of its kind in the state, with a large front porch that still serves as a local focal point. Noted for its humour, a dog is the town's ceremonial mayor.
The state’s first certified trail town, Dawson Springs sits at the edge of Pennyrile State Park in western Kentucky and has long been a gateway to the great outdoors. Its beautiful lake, the 13-mile (21km) scenic Pennyrile nature walk and horse trails draw adventurous visitors, while its photogenic Main Street is part of a historic district with a museum and arts centre, plus places to eat, stay and stock up on a trip through the region.
The streets of Munfordville are lined with heritage buildings and characterful places, not least the Old Munford Inn (pictured) which dates back to 1810. Kentucky’s very own Stonehenge, a replica of the UK site by late artist Chester Fryer, sits just outside the town. Munfordville is another great entry point for Mammoth Cave National Park too, where you can discover prehistoric treasures.
A hidden gem overflowing with Americana, the little town of Hazel in western Kentucky was named by Fodor’s Travel as one of the top 10 antiquing towns in the US, and it’s easy to see why. Its Main Street is lined with curiosity shops and boutiques stuffed with unique items such as old signage and hand-spun glassware. Collectors spend hours browsing the old emporiums and vintage lovers will certainly not go away empty-handed. Stop by the Blue and White Grill for a delicious piece of coconut cream pie.
Hungry travellers can trace the origins of KFC all the way to the little town of Corbin in southeastern Kentucky at the Sanders Cafe and Museum – the official birthplace of the original crispy fried chicken created by Colonel Sanders. The town is a convenient place to stay overnight if you’re hoping to catch sight of the famous moonbow at nearby Cumberland Falls too, known as Little Niagara for its impressive cascades that are the largest in the southern States.
This historic little town of Maysville on the banks of the Ohio River was established on the site of an 18th-century tavern run by frontiersman Daniel Boone. Many of its old buildings are preserved, making it a great place to experience old Kentucky. Among its quirkier buildings on the US National Register of Historic Places, the Russell Theater in downtown is an atmospheric spot for a weekend movie, while the EAT Gallery and its retro sign show off the town’s timeless heritage.
The attractive town of Versailles is bountiful in the Kentucky hallmarks of bluegrass, horses and bourbon. WinStar Farm is one of the best places to get up close to the State’s famous thoroughbred stallions and Kentucky Derby champions, with stable tours and shuttle rides around the property. At 200-year-old Woodford Reserve – a National Historic Landmark – bourbon blends with history, while nearby Kentucky Castle is the area’s very own Palace of Versailles with guest rooms where you can stay the night.
Another town drenched in historic charm, Harrodsburg is Kentucky’s oldest settlement west of the Appalachian Mountains. Old Fort Harrod State Park features a reconstruction of the original settlement and those following the Lincoln Heritage Scenic Highway should visit the Lincoln Marriage Temple, where the former president’s parents wed in 1806. A highlight of Harrodsburg is pretty Pleasant Hill (pictured) with 34 original structures once home to the USA's third largest Shaker community.
The little city of Owensboro may be the fourth most populated area in the state but it’s brimming with country charm. Capital of Bluegrass, it’s one of the best places in the state to experience its famed live music scene and as Kentucky’s festival city, it hosts more than 20 annual events. Positioned along the Country Music Highway, it’s home to the Bluegrass Music Hall of Fame and Museum (pictured) and also sits on the iconic Route 66, making it an ideal stop on a classic American road trip.
As well as being blessed with a picture-perfect downtown centred on 19th-century Fountain Square Park, Bowling Green is bursting with vintage attractions including the Historic Railpark and Train Museum and the National Corvette Museum dedicated to the classic cars built exclusively in the town. Steeped in history, Bowling Green is a key stop on the Civil War Discovery Trail with signs of the past at every turn, while Lost River Cave is nearby, offering subterranean cave boat tours.
The gateway to Kentucky’s cave region and the famous Mammoth Cave National Park, which contains the world’s longest cave system, Cave City is a great base to explore the area’s 84 miles (135km) of trails and countless natural attractions. Alongside Mammoth Cave, explorers can also visit Hidden River Cave, Diamond Caverns and Cub Run Cave, and local outfitters can arrange horse riding and canoeing tours. The town has plenty of places to stay and eat, including tasty grill house Bucky Bee’s BBQ.
Sleepy Bloomfield in central Kentucky’s Bluegrass region is older than the state itself. The first settlers arrived in the 1700s, and its agricultural industry took off quickly. This included the establishment of a flour mill and tobacco auction house in the 19th century. Traces of its history can still be seen in the town’s architecture. Built in 1835, the Newell B. McClaskey House and plantation is listed on the US National Register of Historic Places.
In far western Kentucky, the Land Between the Lakes – amid Kentucky Lake and Lake Barkley – is a great place to get back to nature with more than 170,000 acres of forest, plus many miles of trails and scenic roads. The charming town of Hardin has its own marina with views over the lake – consider stopping for lunch at Cindy’s on the Barge, renowned for good food at affordable prices.
On the scenic Kentucky River, Winchester oozes old-time Southern charm and its downtown Victorian-era architecture is meticulously preserved. Authentic Kentucky beer cheese is said to have been invented here, and the town is home to the Beer Cheese Trail with a string of eight local restaurants and eateries – some in great riverside spots – serving up variations on the original recipe. The annual Beer Cheese Festival is hosted every June.
On Kentucky’s Civil War Heritage Trail and the Lincoln Heritage Scenic Highway, Hodgenville is steeped in history. As the birthplace of legendary US president Abraham Lincoln, the area includes a national historical park with an impressive memorial building dedicated to Lincoln, as well as a dedicated statue and museum within the town centre, plus a reconstruction of his boyhood home at nearby Knob Creek Farm.
Kentucky’s state capital is actually a small historic town full of rural Kentucky charm, surrounded by verdant horse farms and artisanal distilleries including the Buffalo Trace Distillery. As the resting place of celebrated frontiersman Daniel Boone, and a key stop on the Civil War Heritage Trail, Frankfort has a deep history that can be glimpsed in the old buildings of downtown, as well as at several history and art museums and the beautiful State Capitol building.
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