17 Charming Small Towns in Kentucky You Need to Visit (2024)

There’s a lot going on in Kentucky.

Spend some time in the state’s great cities and you can take in everything from the unique sights of the Kentucky Derby to the sweet sounds of bluegrass music to the world’s best bourbon.

If you step outside the cities, there’s even more to be found here!

Between the winding bends of the Ohio River and the foothills of the Appalachians lies a whole world of diverse communities, full of varied attractions that range from the world’s longest cave system to the simple comforts of warm Southern hospitality.

Deep in history and nestled amid the rolling farmland of this great state, the small towns in Kentucky offer something up for everybody.

Here, we’ll give you a guided tour of 17 of the best small towns in Kentucky.

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1. Henderson: best small towns in Kentucky to visit

Henderson Kentucky — Image: Henderson Ghost Sign Dec 2015 2. Anthony. [CC BY-ND 2.0] via Flickr

Nestled in a bend of the Ohio River, you’ll find the charming slice of small-town life that is Henderson.

Henderson is a place where rural life moves at the same casual pace as the river that it borders, but mixed into it is an up-and-coming food scene that is bolstered by a thriving arts community.

This charming riverfront town is known for the well-known artist and naturalist John James Audubon, whose family once found a home here, drawn in by the wide-open surrounds and the steady meander of the riverside life.

Visit the Audubon Museum for a deep dive into his life and the early history of the area, or go out and explore the John James Audubon State Park’s miles of hiking trails, discovering the fertile landscapes and rich wildlife that brought him here.

In the middle of all of this is the charming downtown, filled with all the restaurants, local stores, and culture that set Henderson out as one of the best small towns in Kentucky.

2. Rosine

In Rosine, it’s all about the music.

While the town itself is tiny, the father of Bluegrass music, Bill Monroe, does a brilliant job of keeping that legacy going!

You can visit the great man’s grave or the Bill Monroe museum to learn more about his life and the pivotal role of Bluegrass music in growing the authentic culture of the area.

And, if you want a taste of the real thing, just head over to The Rosine Barn Jamboree on a Saturday for great live music in a barn on the edge of town, complete with all the barbeque and guitar a heart could wish for.

3. Greenville: Kentucky small towns

Here in the rolling hills of the Western part of the state, you can find all the charm and culture of Greenville.

This used to be coal country, but now is known more for its long history, state parks, and some of the best food and drink you can find in the area.

You can’t leave Greenville without making a quick stop at the J & H Bakery.

J&H Bakery, best donuts in Kentucky — Photo credit: J & H Bakery Facebook Page

Locals have stated that this bakery has the “best donuts in town.”

See for yourself!

4. La Grange

You can find this charming little town just a little bit outside the reach of Louisville, and this mingling of small-town life and proximity to the state’s cities is one of the main draws of the town.

You can spend your time meandering through the town’s wide open green spaces or head out on the hiking trails that wind through the area’s rich wildlife, in the Creasey Mahan Nature Preserve.

If nature isn’t our thing, you can instead explore the area’s past at the Oldham County Historic Center, or pop into one of the locally owned stores or restaurants.

And then, when the city calls, you’re in driving distance of your pick of the Kentucky cities, making it the perfect base for exploring the state and one of the best small towns in Kentucky to live in.

5. Morehead

Moorehead Kentucky — Image: Moorhead. Nicki. [CC BY-ND 2.0] via Flickr

Morehead is a heady mix of culture and nature, giving visitors a wide array of choices for how to pass their time here.

The nearby Daniel Boone National Forest is full of trails winding between the woodland, offering outdoors enthusiasts the perfect space to venture out for a day hike or spend some time camping under the stars.

Or, head out to Cave Run Lake for some of the region’s best fishing and swimming, passing the day in the still, tree-lined waters.

In town, Morehead State University regularly puts on cultural events of all shapes and sizes, as well as the Rowan County Arts Center and Morehead Theatre, meaning there’s always something available for those looking to mingle small-town living with a varied cultural output.

6. Berea

Image: Berea Pinnacles. Anthony. [CC BY-ND 2.0] via Flickr

Of all the charming, quaint towns in Kentucky, few pack as much in as Berea.

Wandering around the historic downtown, you’ll be spoilt for choice for traditional restaurants, historic, white-pillared buildings, and galleries that reflect the town’s thriving art scene.

Similar to Morehead, it is known for its college, and this one is famed for its liberal arts, helping add to the town’s culture of sustainable creativity that has earned it the title of the Folk Arts & Crafts Capital of Kentucky.

Meander around the artisan village to see local artists creating and selling their work, before stopping off at one of the town’s family-owned restaurants for some true Kentucky fare.

7. Cadiz

By now, you’ll have seen there are a fair few cute towns in Kentucky, but Cadiz is a gem.

It’s deep in the heart of the Kentucky countryside, near to the wide Cumberland River.

If you’re looking for a town to use as a base for hiking, fishing, or camping, then you’ll find few better.

The town itself is beautiful as well, home to antebellum mansions and a historic downtown area, full of quirky independent stores.

Buried here near the river, in the deep green of the countryside, it’s the perfect place to get away from it all.

8. Danville: charming towns in Kentucky

Image: Danville’s North Theater. Waldo Jaquith. [CC BY-SA 2.0] via Flickr

You’ll find Danville deep in the heart of Bluegrass country, filled with all of the small-town atmosphere and warm Southern hospitality that you could ever hope to find.

The lovely downtown area is built around boutique and restaurant-filled historic buildings, the perfect afternoon’s meander as you amble along at the steady pace of life here.

If you’re looking for bourbon (after all, you are in Kentucky) you’re spoilt for choice.

The town feeds into the famous Kentucky Bourbon Trail, and if you’re feeling thirsty head over to Wilderness Trail Distillery for some of their fine, fine spirits, made using locally grown grains.

And if it’s something genuinely unique that you’re after, swing by the Great American Dollhouse Museum for an experience you won’t quite find anywhere else.

9. Grand Rivers

Grand Rivers is tiny.

Really tiny.

At the last count, 352 people lived here, making it the perfect place to get an authentic small-town feeling.

Here, it’s all about the water that flanks the town on both sides.

The town is built between Lake Barley and Kentucky Lake and draws in fishing and water sports enthusiasts all year round.

Whenever you’re in town, drop in to Patti’s 1880’s Settlement for some classic Kentucky food.

If it’s your first time, try the 2-inch pork chops.

Bring an appetite!

10. Glasgow: quaint towns in Kentucky

The landscape around Glasgow is rolling, tree-covered hills that span out as far as you can see.

There’s great fishing in the lakes and rivers that flow through here, great hiking in the mile after mile of trails that span around.

There’s even some golf as well.

But it’s below the ground that the area’s real appeal lies.

The town is right on the edge of Kentucky’s famous cave country, a genuinely unique part of America.

It makes the perfect base to explore Mammoth Cave National Park, home to the world’s longest-known cave system.

Take a tour, or explore this hidden underworld by yourself, walking down winding passages of and gaping caverns of night-dark rock.

For the claustrophobes out there, don’t worry, there’s plenty above ground as well.

Try and time your trip to coincide with the Glasgow Highland games, an annual celebration of the area’s Scottish heritage that is a weekend packed full with kilts and fun.

11. Harrodsburg

There are a few cute towns in Kentucky, but Harrodsburg lays claim to being the oldest and one of the best.

The town has flourished throughout the years (George Washington even visited here during the Revolutionary War) and you can find examples of this history everywhere, from the historic buildings that make up downtown to the fort that dominates the Old Fort Harrod State Park.

If you even want your accommodation to be historic, book a room at the lovely Beaumont Inn to sleep amid a real feeling of old-world charm and warm Southern hospitality.

12. Lawrenceburg

Image: Joe Blackburn Bridge. Rob Alter. [CC by 2.0] via Flickr

Lawrenceburg is the quintessential Kentucky town, a quaint place of easy living, good food, and fantastic bourbon.

It’s surrounded by the rolling hills of the central part of the state, and offers everything you’re looking for in a quiet getaway, but with enough to always keep you entertained.

The main draw of the area is definitely its bourbon.

This is pure bourbon country, and first-timers and aficionados alike will be spoilt for choice.

Head over to either the Wild Turkey or Four Roses distilleries to see how it’s made and, equally as importantly, treat yourself to a few samples.

13. Midway: cute towns in Kentucky

Deep in the Bluegrass region, Midway is a town of just over 1,500 people enjoying this quiet, calm stretch of the state.

The old-school downtown area is made up of charming streets of different-colored historic buildings housing mom-and-pop stores and restaurants serving up classic southern fare (go check out the steaks at The Brown barrel & Blind Harry’s or grab a seat at their classic polished-wood bar).

But it’s horses that the town is truly famous for.

Specifically, some of the finest thoroughbred horses in the world.

Equestrian life is the life here, and the town is home to multiple ranches and stables breeding world-beating horses, all enjoying the wide open landscape that stretches out around the town.

14. Mt. Sterling

Nestled in the foothills of the Appalachians, Mt. Sterling is one of the best little towns in Kentucky.

Like Midway, the town is known for its equestrian culture, but this is woven into a thriving arts scene and a feeling of real history to the place.

A lot of effort has been put into revitalizing the downtown area over recent years, and the results are plain to see in its mingling of charming stores, artsy pop-ups, and restaurants serving some of the best food in the region.

If you want to get the inside track on the town’s history and how all of this came to be, pop over to the Montgomery County History Museum.

And all of this against the beautiful backdrop of the surrounding landscape.

After you’ve meandered around town, take a trip out to some of the surrounding parks and enjoy the open space with the Appalachians gradually growing up to the sky behind you.

15. London

London mixes natural charm with a surprising amount of cultural output.

The town is home to a range of galleries and the London Community Center, which is known for regular events that it hosts throughout the town.

It’s most famous as the cycling capital of Kentucky because of the trails and routes that have been put in place around the town and spreading out into the rolling countryside around.

It’s a great way to explore the many sides of this charming corner of Kentucky.

16. Paris

Paris Kentucky — Image: Paris, Kentucky 2. Chris M Morris. [CC by 2.0] via Flickr

It might not have the built-up glamor of its namesake, but Paris has its own kind of charm.

It’s a real community town, built around a feeling of genuine hospitality and small-town warmth.

You can find locally made bourbon, antique stores, mom-and-pop restaurants, it’s downtown area is a warren of different, quirky delights.

The big draw is the Bourbon County fair, an annual weekend-long event that brings people together to celebrate the area, its thriving agricultural heritage, and, of course, bourbon.

(And there’s even an Eiffel Tower, it’s just a little smaller!)

17. Hodgenville: small towns or cities in Kentucky

Central Town of Hodgenville — Image: Central town of Hodgenville. daveynin. [CC BY 2.0] via Flickr

Last but not least, one of our favorite small towns in Kentucky, Hodgenville.

Whether you’re looking for history, hiking, or just a little bit of peace and quiet, Hodgenville has you covered!

The town is most famous for being the birthplace of President Abraham Lincoln and you can explore the Abraham Lincoln Birthplace National Historical Park to find out more about the great man and the world he left behind, climbing the pale stone steps with the dense green of the woodlands either side of you towards the classical, pillared building itself.

Beyond Lincoln, the town is nestled in some of the state’s best countryside, offering great hiking and fishing.

All in all, if you’re looking for a classic Kentucky town with some classic quiet rural life, come along to Hodgenville.

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