15 Best Small Towns to Visit in Kentucky

It’s the perfect destination for those wanting to see the small-town side of the USA, where you’re likely to find friendly locals, beautiful nature reserves, and quirky restaurants and shops at just about any small town that you wander into.

The birthplace of both President Lincoln and Bill Monroe, the bourbon capital of the world, and a perfect place to embark on adventures, Kentucky is one of the most underrated states to visit during your time in the USA.

Aside from small towns, Kentucky is also renowned for having over hundreds of miles of national parks, lakes, rivers, and even caves for adventure travellers to get their outdoor thrill.

Of course, the famous Kentucky Derby horse race is a popular time to visit Kentucky, though its truly a fun place to visit all-year-around. Visit during a public holiday and there’s sure to be some local festivity taking place. Visiting during spring, summer, and autumn will help you get a well-rounded experience of Kentucky where you can pair outdoor activities seamlessly with indoor options.

Each small-town listed has its own personality and offers a one-of-a-kind perspective to Kentucky. From trail towns to hubs for artists to towns that border the Appalachians to those nestling next to Daniel Boone country, these towns might not be great in population are rich in history, hospitality, and culture.

Here are the top fifteen small towns to visit in Kentucky.

1. Somerset

What better way to have fun with your friends and family than to rent a houseboat? Residents of Kentucky love houseboating and frequently hop on deck at Lake Cumberland, located in the small town of Somerset. Travellers can rent boats of all sizes and that will suit most budgets for their water-bound vacation.

Even if you don’t use Somerset as a houseboat hub, you can have a great time exploring Lake Cumberland via its shores by fishing, lounging, kayaking, swimming, skiing, and more. Other natural sights include the Big South Fork Rivers and a gargantuan sandstone bridge.

Somerset is also a convenient point to stay and venture to Daniel Boone National Forest, Big South Fork National River, and board a train to see the Big South Fork Scenic Railway that drives through the surrounding areas.

And all that doesn’t even account for all there is to do in town, like going to SomerSplash water park, attending music festivals, drive-in movies, dining, and visiting the museums!

2. Shelbyville

If you’re an equestrian rider or obsessed with horses, Shelbyville is a must stop destination while in Kentucky. Though Louisville, home to the Kentucky Derby, boasts the largest claim to fame when it comes to equestrian events, there’s fun to be had in Shelbyville, a small town that hosts a yearly horse show. Shelbyville also is known for breeding regal American Saddlebred horses.

Additionally, visitors can pick fruit at the Mulberry Orchard, go wine tasting, browse through antiques at the Ruby Rooster Antique Mall, and Gallrein Farms, a farm that hosts activities for children and adults alike.

No stop to Shelbyville would be complete without a tour of the local distilleries located along the “Bourbon Trail.”

3. Bardstown

Willett Distillery - Bardstown, Kentucky — Willett Distillery – Bardstown, Kentucky

Bardstown is for bourbon lovers, the Bourbon Capital of the World. Home to three well-known distilleries of Barton 1792, Heaven Hill, and Willett Distillery, it’d be a good idea to find a designated driver to take you around this small town’s tasting rooms.

When sober, read up on bourbon’s history at the Oscar Getz Museum of Whiskey History to find out more about this state’s golden export that features exhibits from the pre-Colonial days through the Prohibition to the present.

For additional information on the region, you can also check out the Civil War Museum that hosts relics of one of America’s most influential times in history. There are a few historical and heritage tours that can cover main points of interests and the museums all within a few hours.

Off-beat travellers will love camping at My Old Kentucky Home State Park and searching for the ghosts of Bardstown – allegedly there are many. Come for the bourbon, stay for the local flair.

4. Rosine

Bluegrass fans from all around the globe pour into Rosine, the small town where Bill Monroe, the father of bluegrass, first created his musical magic. Bluegrass pilgrims can visit the home of Bill Monroe, the venues he used to play at, and his grave. Visitors can even view his family photographs out on display.

Additionally, the Rosin Barn Jamboree was once where Bill Monroe fine-tuned his craft and played his last show. Even those who don’t listen to bluegrass can appreciate the atmosphere that the stage still holds today. Next door, fans can go to the Rosine General Store, where locals play music on its front steps.

To complete the bluegrass tour, then head to nearby Owensboro where fans can learn even more about the new music genre at the International Bluegrass Music Museum where an assortment of all types of bluegrass memorabilia are out for everyone to enjoy.

5. Berea

Berea is one of Kentucky’s art hubs of the state that attracts various types of painters, musicians, textile designers, and sculptors. It hosts a vibrant community that is constantly innovating and supporting one another to put out their best work. This all comes together at the annual Berea Craft Festival and can be seen all year long at the Kentucky Artisan Center and the Square Gallery.

The town itself has many historical sites like Berea College built in 1855 that was the region’s first interracial college and a slew of historic restaurants, buildings, and private homes.

6. Hodgenville

Birthplace of Abraham Lincoln, Hodgenville has held an important tie to history throughout the decades. Those who want to trace Lincoln’s heritage can do so by exploring the lush forest trails in the Abraham Lincoln Birthplace National Historical Park and the Abraham Lincoln Boyhood Home, where Honest Abe learned the basics of his education. In town is the Lincoln Museum, a tiny building that features Civil War mementos, newspaper clippings, and even wax statues! Of course, you can also take your picture with a bronze statue of President Lincoln in the town square.

Hodgenville is a small town that transports you back in time where you can see the perspective from one of the nation’s most influential leaders that can be seen within one day.

7. London

Laurel County Court House, London, Kentucky

London, Kentucky, is a small town that caters to residents and travellers alike who are obsessed with the outdoor lifestyle. London is the perfect home base to explore natural features like the Daniel Boone National Forest, Rockcastle River, Laurel River and Laurel Lake, Levi Jackson State Park, and more.

Hikers can trek through the Sheltowee Trace National Recreation Trail while cyclists can weave through the many London-Laurel County cycling routes. For those who like a little fuel with their fun, there’s the Wildcat Mountain ATV Park.

There is also the historical treasure of the Camp Wildcat Battlefield, a field that has been altered very little since its battlefield days – unlike many of the others nearby, which have drastically changed. For an interesting live view of history, go to watch or participate in a battle re-enactment.

8. Pikeville

If you wanted to see a well-rounded view of all that Kentucky has to offer but could only visit one town, Pikeville would be an incredible contender.

Outdoor enthusiasts can explore the Appalachian Mountains, go horseback riding, hiking, mountain biking, kayaking, and even ziplining.

Also, there are constant performing arts shows playing at the Jenny Wiley Theatre and the Artists Collaborative Theatre. Live music – especially of the country variety — can be heard all throughout the town, either as an organize performance or spontaneously on the streets.

History buffs can attend historical Hatfield and McCoy feud site, where two rival families fought strategically over local land and business – developing some of the state’s strongest points of interests along the way.

9. Glasgow

With the tagline of “A little bit of Scotland in Kentucky,” Glasgow surely is a small town that’s unlike anywhere else in the state. Its nod to Scotland takes place during the annual Scottish Highland Games.

Glasgow is the perfect home base to explore some of Kentucky’s most notable natural landmarks like Mammoth Cave National Park — a spelunker’s paradise, the Brigadoon State Nature Reserve, the Diamond Caverns, and the Barren River Lake. Adventure travellers will love all the hiking, camping, swimming, and other outdoor activities that the town is the perfect portal to.

There is also the Historic Plaza Theatre, Museum of the Barrens, Veterans Wall of Honor, and Fort Williams, where you can put yourself back in time and imagine what life was like during the Civil War.

10. Murray

Named the “Friendliest Small Town in America” by USA Today, you have to stop by Murray when in Kentucky to see whether the town lives up to its accolade.

What makes Murray so welcoming? Well, its proximity to Kentucky Lake and Land Between Lakes recreation area probably makes its residents feel always at ease. There, you can fish, hike, kayak, watch wildlife, and play golf all around bodies of water that turn pink as soon as its sunset.

Or, maybe the locals partake in a bit of retail therapy and support their small businesses at Murray’s strip of boutique shops. The plethora of live music of course helps residents stay upbeat as well.

The best way to experience Murray is to wander around and ask the locals what their favorite things to do are.

11. Greenville

Postcard perfect, Greenville is a manicured small town with stunning heritage buildings, locally owned boutiques, and a vibrant community with regular activities for locals and visitors to join in on. Though you can count your accommodation options on one hand, visitors often come back time and time again just because of Greenville’s hospitality.

Some of its small-town highlights include the 12-acre forest at Brizendine Brothers Nature Park, the six mile Rails to Trails walk, the vast Lake Malone State Park, and a one-of-a-kind gazebo called the Summerhouse perfect for picnics at the city park.

There are also local theatre performances, veteran tributes, and restaurants serving classic Kentucky fare.

12. Lebanon

The heart of the Bourbon Belt Trail, which spans over eighty miles long and links ten bourbon distilleries, is Lebanon. Lebanon hosts the famous bourbon distilleries of Maker’s Mark and Limestone Branch as well as the bourbon barrel making company of Kentucky Cooperage which makes over 600,000 bourbon barrels per year. If wine is your alcoholic vice of choice, there is also the Whitemoon Winery.

Lebanon is a lively small town with civil war sites, a heritage center, Pope’s Creek Ranch, and the Turtleman museum, a museum created after a local folk hero, Ernie Lee Brown Jr., who wrangles turtles and has his own show on Animal Planet.

Bizarre but interesting, Lebanon has quite a bit to see for being such a small town.

13. La Grange

La Grange, Kentucky is a small town that takes pride in the fact that there might well be more resident farm animals than humans in its population. There are multiple nearby hands-on farm tours where visitors can learn to care for farm animals, farm sustainably, ride horses, and even create a meal with local farm fare!

For a locomotive spin, La Grange is also the only town in the country where a freight train chugs along the main street – meaning that you’ll hear a loud noise and probably feel a rumble as it passes through while you visit.

Couples will love staying in antique, spacious, and tastefully decorated B&Bs that are away from any semblance of a busy life. Best of all, La Grange is near attractions like the Kentucky Derby Museum, Whiskey Row, and live bluegrass music venues.

14. Maysville

Maysville residents love to have fun and it shows. This small town located on the banks of the Ohio River is easily accessible and has many historic sites, dining venues, and outdoor activities that will welcome any type of traveller.

Theatre buffs will love watching live performances at the Washington Opera House, built in 1889 and at the Russell Theatre, currently being restored to feature a star-studded ceiling. For visual artists, there is also the Kentucky Gateway Museum Center featuring a stunning 1/12 miniature collection.

With zip lining, a constant roster of festivals, and a handful of old-timer bars, Maysville residents simply love to have a good time.

15. Midway

Picturesque with under 2,000 residents, Midway has postcard perfect buildings, antique shops, wildlife sanctuaries, galleries, and restaurants with top notch customer service.

The town of Midway has catered to tourists by offering a cell phone walking tour, where you can hear in depth about the town’s highlights by picking up a map at City Hall and dialling a phone number for a guided experience. A historical city tapping into the technology era? Now that’s innovative.

Aside from the town square, there are museums, orchards, vineyards, and even an adventure center to round out your time at this interesting small town.