Updated May 2025 by Gaye Swan

Kentucky may be celebrated for its world-class horse racing, legendary bourbon, and fierce basketball pride, but there’s so much more to discover! Tucked between rolling hills and scenic byways, the Bluegrass State is dotted with small towns that brim with personality, creativity, and local flavor. From vibrant arts scenes and mouthwatering BBQ to historic gems, craft breweries, lush green spaces, and unexpected delights, here are seven small towns in Kentucky you should visit.

Table of Contents
  1. Central City, KY: Small Town, Big Music
  2. Paducah, KY: Rich in History and Art
  3. Madisonville, KY: Nature and Outdoor Activities Abound
  4. Henderson, KY: Where History and Outdoors Meet
  5. Bardstown, KY: A Bourbon Enthusiast’s Dream
  6. Midway, KY: A Historic Railroad Town
  7. Maysville, KY: A Scenic River Town with Tons of Art

Central City, KY: Small Town, Big Music

Located less than two hours from Louisville, in Muhlenberg County, Central City is a small gem with a sparkling musical heritage. The hometown of Rock & Roll Hall of Famers The Everly Brothers, Grammy-winner John Prine, and world-renowned flutist Jim Walker, this lovely little town has several attractions that make it well worth a visit.

A bronze statue of a man playing guitar stands by a black granite monument engraved with his portrait and signature, creating a unique tribute in Western Kentucky near a grassy area and pharmacy building.Pin
A stop on the Kentucky Music Trail, the well-kept Festival Square is a charming green space that pays homage to the musical legends who have called Central City home. Image: Kentucky Tourism

WHILE YOU’RE THERE

At The Muhlenberg Music & History Museum, explore the legacy of The Everly Brothers, whose blend of folk, bluegrass, and country music sung in close harmony made them one of music’s great vocal partnerships. Singer-songwriter John Prine made Muhlenberg famous with his hit “Paradise,” and you can listen to it on the jukebox! Just behind the Music Museum, you’ll find a tribute to the world of motorsports at the spacious Kentucky MotorSports Hall of Fame and Museum — from Soap Box Derby winners and race cars to TV stunt cars and more.

For the arts, open-air Lu-Ray Park & Amphitheater boasts an outdoor amphitheater, concession stand, Veterans memorial, and covered outdoor pavilion, all in a welcoming, park-like setting. Before you leave town, grab a bite at Holly J.’s Grill. Open, airy, and inviting, the restaurant has a tasty menu and a fun upstairs bar.

Interior of a music museum in Western Kentucky featuring records, album displays, mannequin figures in tuxedos, and a wall map of the United States with flags and music-themed decor.Pin
At The Muhlenberg Music & History Museum, you can learn about Singer-songwriter and Guitarist Merle Travis, as well as flutist Jim Walker, perhaps best known for his work on the score of the blockbuster movie Titanic. Image: Kentucky Tourism
Indoor display of race cars and motorcycles with a red "ATLANTIC" neon sign overhead; posters and flags decorate the background.Pin
Explore the world of motorsports at the Kentucky Motorsports Hall of Fame and Museum. Image: Kentucky Tourism

Paducah, KY: Rich in History and Art

Lovely Paducah is bursting with history and art! Located at the confluence of the Ohio and Tennessee Rivers, the town was founded by General William Clark of the famous Lewis and Clark expedition. Best known today as “Quilt City USA,” Paducah is a UNESCO Creative City for Crafts & Folk Art — one of only a handful of UNESCO Creative Cities in the country. Just a short stroll from the riverfront, Paducah’s Lower Town Arts District is a vibrant and walkable neighborhood, home to galleries and studios, including several where you can meet artists and see works-in-progress.

A colorful quilt featuring NASA and space-themed designs hangs on display alongside two other decorative quilts, highlighting the big experiences found in small towns like those in Western Kentucky.Pin
In 1984, local entrepreneurs founded the American Quilter’s Society, which hosts QuiltWeek. Over 30,000 quilters from every continent come to celebrate, compete, and showcase fiber art at the internationally attended annual event. We can attest, the talent is mind-blowing! Image: Kentucky Tourism

WHILE YOU’RE THERE

Find out more about Paducah’s history as you explore the historic riverfront and its stunning Wall to Wall mural project — a series of over 60 murals that depict the city’s history. Every April, Paducah transforms for its signature event, QuiltWeek, a fantastic display of international fiber artists. If you can’t make QuiltWeek, the National Quilt Museum is the premier institution for contemporary quilt and fiber art, housing over 650 quilts with rotating exhibits.

Fiber arts aren’t the only highlight in town; Purple Toad Winery has perfected the art of making award-winning wine. If artisan beers are more your speed, begin your discovery of the region’s diverse brews at a fun stop on the West Kentucky Brewery Hop, Paducah Beer Werks (and get a delicious meal while you’re there).

A metal building with a covered patio and outdoor seating sits on a grassy lawn in Western Kentucky, featuring a "Purple Toad" sign, trees, and another small town building in the background.Pin
Purple Toad Winery is part of the Western Kentucky Wine Trail, which connects nine charming local wineries across the region. Image: Kentucky Tourism
Four people walk along a sidewalk in Western Kentucky, passing a long mural of historical scenes, enjoying big experiences in one of the region’s charming small towns on a sunny day.Pin
A stroll along the riverfront is a perfect way to learn about Paducah’s history from detailed, life-like murals. Image: Kentucky Tourism

Madisonville, KY: Nature and Outdoor Activities Abound

Home to scenic trails, peaceful lakes, and rolling grasslands, Madisonville is home to an interesting variety of outdoor activities. Plus, you’ll find great food, a state-of-the-art fine arts theatre and gallery, and a charmingly historic downtown. It’s also a stop on the West Kentucky Brewery Hop, and you’ll find a lovely spot on the Kentucky Garden Trail, which features 12 of the state’s most beautiful gardens and arboreta.

A large rock with a plaque sits on a grassy field near a paved path in a Western Kentucky park, where small towns offer big experiences among trees, a playground, and a metal sculpture in the background.Pin
Gifted to the City of Madisonville by Dr. Merle and Glema Mahr, Mahr Park Arboretum is a gorgeous stop on the Kentucky Garden Trail with lots of recreational and educational opportunities — trails, a nature play area, fishing ponds, a kayak launch, a dog park, disc golf courses, and picnic pavilions. Image: Kentucky Tourism

WHILE YOU’RE THERE

Outdoor adventurists will find lots to love in Madisonville. One of the crowning glories of the region is the Mahr Park Arboretum. With 265 acres of natural beauty, walking trails, fishing ponds, a kayak launch, disc golf courses, birdwatching, and picnic pavilions, this gem is perfect for nature lovers and families. Madisonville City Park features an 18-hole mini-golf course, swimming pool, splash pad, and regular community events. You can also golf, mountain bike, and much more!

After a day outdoors, you’ll want a hearty, delicious meal. Thankfully, Brother’s Bar-B-Que has just what you’re looking for. And don’t miss out on a visit to Tradewater Brewing Company, Madisonville’s first craft brewery. If the arts interest you, check out the Glema Mahr Center for the Arts!

A bartender places a glass of dark beer on the bar next to a pale ale, both branded with the Tradewater Brewing Company logo—a proud taste of Western Kentucky’s small towns.Pin
Tradewater Brewing Company is another fun stop on the West Kentucky Brewery Hop. Image: Kentucky Tourism
A grilled steak with sauce on the side, served with a dinner roll, macaroni and cheese, and a bowl of potato salad—classic Western Kentucky comfort for those seeking Big Experiences in Small Towns.Pin
Bring your appetite to Brother’s Bar-B-Que! Image: Facebook

Henderson, KY: Where History and Outdoors Meet

Nestled along the Ohio River, historic Henderson was once a major center for dark tobacco production and export. Its historic mansions and charming downtown architecture echo the city’s days of prosperity. Famous naturalist John James Audubon and four former Kentucky governors lived here. Today, peaceful riverfront parks offer scenic views, playgrounds, and green spaces that beckon visitors and residents alike.

A large grassy park with scattered trees, benches, and a metal truss railroad bridge in the background offers big experiences on a clear day—capturing the charm found in small towns across Western Kentucky.Pin
The Henderson Riverwalk offers scenic views, playgrounds, and recreational spaces along the Ohio River. Image: Kentucky Tourism

WHILE YOU’RE THERE

The John James Audubon State Park features a museum with Audubon’s works, hiking trails, birdwatching, beautiful architecture, nature programs, and a fascinating look at Audubon himself. After taking a stroll on the Henderson Riverwalk, Red Banks Park, or Sunset Park, stop by the Henderson Tourist Commission and Art Gallery to visit Gallery 101, which features rotating art exhibitions and stunning views of the Ohio River. Next, try the self-guided Audubon Sculpture Tour.

Eat lunch at Cap & Cork, a delicious downtown steakhouse and bourbon bar (ask for a bourbon flight and thank us later!). Our list would not be complete without an artisan brewery. Henderson Brewing Co. is – yep, you guessed it, another stellar spot on the West Kentucky Brewery Hop. It’s one you don’t want to miss.

Dinner at Farmer and Frenchman Winery & Cafe is an absolute must. Spend the night and enjoy a stellar homemade breakfast at the delightful L&N Bed and Breakfast.

A stone building with a conical-roofed round tower, arched entryway, and surrounding trees under a partly cloudy sky.Pin
Henderson’s most famous historical inhabitant was the noted naturalist John James Audubon, who was drawn to Henderson’s wooded hills and lush vegetation. Today, the John James Audubon State Park is the home to the Audubon Museum & Nature Center, which explores his life and legacy. Image: Kentucky Tourism
A glass of white wine and a plate with salad and cheese are set on a wooden railing, overlooking a vineyard and open fields under a clear blue sky.Pin
A feast for the senses awaits you at Farmer and Frenchman Winery & Cafe. Image: Facebook

Bardstown, KY: A Bourbon Enthusiast’s Dream

Founded in 1780, Bardstown is Kentucky’s second-oldest city and the official Bourbon Capital of the World. Find nine top-notch bourbon distilleries (plus two more set to open by the end of 2022) within 16 miles of charming downtown Bardstown. This vibrant town is home to more than 300 buildings on the National Register of Historic Places, and nearly 200 of those are in the downtown district. Bardstown boasts cozy pubs and taverns, a packed cultural events calendar, as well as fabulous golf and river sports, both whitewater and calm-water.

With a population still under 14,000, and so much to explore, Bardstown is chock-full of small-town Southern charm that will leave you in the highest spirits.

The Bardstown, Kentucky Main Street under a bright blue sky.Pin
Bardstown has been named “The Most Beautiful Small Town in America” by USA Today and Rand McNally. Image: Visit Bardstown

WHILE YOU’RE THERE

Of course, you cannot skip visiting one (or more) of the area’s bourbon distilleries, such as Willett and Barton 1792. Aficionados or those eager to learn and taste can visit Heaven Hill Distilleries Bourbon Heritage Center and Whisky Magazine’s attraction of the year, the Oscar Getz Museum of Whiskey History. Bardstown is also home to the state’s oldest bar, Talbott Tavern, and several locally-owned restaurants and shops. Stop in the Blind Pig Bourbon Marketplace to pick up a rare bottle, then eat, drink, and sleep at the luxurious Bourbon Manor Bed & Breakfast.

My Old Kentucky HomePin
“My Old Kentucky Home” is a historic 19th-century mansion with exquisite 200-year-old artifacts, lush gardens, manicured grounds, and rich farmlands. Plus, your tour guides will perform the famous American ballad “My Old Kentucky Home,” written by composer Stephen Foster. Image: My Old Kentucky Home

Midway, KY: A Historic Railroad Town

Midway is home to some of the world’s top thoroughbred horse farms and is in the heart of Kentucky’s Bluegrass Region. Built on the fortune of its intersecting railroad, historic Midway was revitalized in the 1970s and ’80s and enjoys a well-deserved reputation as one of Kentucky’s most charming small towns with antiques, crafts, clothes, and culinary hot spots.

Several freight trains still use the active tracks running through Railroad Street, preserving Midway’s authentic historic atmosphere. And don’t let the town’s population of around 3,000 fool you! Visitors and surrounding locals alike flock to Midway from all over after visiting horse farms and bourbon distilleries. We recommend pushing this one to the top of your road trip list!

Equus Run Vineyards from abovePin
Equus Run Vineyards is a slice of wine country in bourbon and horse country. Image: Jeff Ashcraft

WHILE YOU’RE THERE

Stop into the Bluegrass Railroad Museum or explore nature at the expansive, walking trail-filled Walter Bradley Park. You should also plan to enjoy a wine tasting at Equus Run Vineyard. Opened in 1998, some of Kentucky’s finest wines are crafted in this winery. You can take a self-guided stroll through its rolling landscape or book a private tour and tasting.

Refuel at the soon-to-be-opened Black Type Company for coffee, wine, books, and gifts,  and discover some fine menswear at Crittenden Rawlings, a shop that will transport you to the English countryside. After a day of exploring, snag a coveted reservation at Heirloom or Holly Hill Inn for delicious dishes by two of Kentucky’s best-known chefs.

Weisenburg Mill Midway KentuckyPin
The Weisenberger Mill has operated at the same site on South Elkhorn Creek since 1865 and still churns out about 70 products you can purchase, such as flour, pizza dough, cornmeal, biscuit mix, and more. Image: Ashley Wyatt

Maysville, KY: A Scenic River Town with Tons of Art

Our small-town Kentucky road trip continues northeast (an hour from Lexington) to the charming town of Maysville. Established in 1787, the waterfront town of about 10,000 residents was built due to its importance as a trade port on the Ohio River.

Today, Maysville preserves its historical backdrop with a heaping dash of undeniable charm, mixed with art-centric cultural outlets and outdoor adventure. A player in Kentucky’s bourbon production, it’s said that the term “Bourbon Whiskey” was coined in Maysville, back when barrels were stamped with the phrase before being shipped downriver to New Orleans. The town now lies on the new and popular B-Line: a Bourbon-centric trail of distilleries, taverns, and restaurants that connects Maysville with other small towns in Northern Kentucky.

Babz BistroPin
The coolest backyard vibes can be found at Babz Bistro — a creative bistro-on-wheels concept serving up Southern dishes in a tranquil garden. Image: Babz Bistro

WHILE YOU’RE THERE

Maysville is rich with art of all kinds. Visit singer Rosemary Clooney’s former home, and let the music move you in the newly restored Washington Opera House (run by the oldest theater group in Kentucky, the Maysville Players). You can also discover an awe-inspiring collection of miniatures by master artisans at the Kentucky Gateway Museum Center.

Also at the museum, The Old Pogue Experience takes you from the 1791 Whiskey Tax Act Rebellion to the heyday of bourbon making in the area, through Prohibition, and to the rebirth of original Kentucky Bourbon.

After a packed day of exploring, grab a bite at the European-esque Parc Café, and book a room at the Moon River Bed and Breakfast to be steps from all the action. And, if school is in session, you can pop into College Café for a meal freshly prepared by students of the Maysville Institute of Culinary Arts.

Maysville, KY architecturePin
Colorful 19th-century row houses and New Orleans-style architecture are two types of homes you’ll see in Maysville. Image: Gardens To Gables

Let’s raise a three-finger-filled glass of bourbon to these Kentucky small towns — and all the others you will stumble upon along the way!

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Zoe Yarborough
About the Author
Zoe Yarborough

Zoe is a StyleBlueprint staff writer, Charlotte native, Washington & Lee graduate, and Nashville transplant of eleven years. She teaches Pilates, helps manage recording artists, and likes to "research" Germantown's food scene.