The Most Charming Small Towns In Kentucky

Oldham County is one of the best places to visit in the fall, or all year long! You’ll find southern charm in each small town as well as a variety of things to do and see, from 15 Farm Tours to farm-to-table meals at Hermitage Farm’s Barn8 Restaurant to the many upcoming holiday events – make it a weekend trip or week-long break from your daily routine. You’ll be sure to be amazed at all the county has to offer.

Southern Living
By Kathy Witt
October 13, 2023

With pretty downtowns and distinctive personalities, Kentucky’s small towns are rich in history, conscientious about traditions, and full of charm. “We strive to make our city a great place to live, work, and play, but none of that is possible without the genuine charm and hospitality of our citizens,” said Matt Wallingford, city manager of Maysville, a small town steeped in culture, commerce, and the arts located along the Ohio River.

From quaint town squares and museums to train rides and natural geologic wonders, these small Kentucky towns offer unforgettable experiences for any kind of weekend getaway.

Bellevue
Population: 5,524

Just minutes away from the bustling Newport on the Levee entertainment complex, Bellevue blends city convenience with the yesteryear charm of historic Kentucky river towns. Fairfield Avenue, its tree-lined main thoroughfare, has been the beating heart of this close-knit community since the 1800s. Independently owned small businesses take up residence here in the colorful Italianate buildings and unique storefronts.

Named for its beautiful view of the Ohio River and Cincinnati skyline, Bellevue has a lively downtown that hosts numerous street festivals and community events: farmers markets, art shows, parades, concerts, and more. Visitors find everything from a retro ice cream parlor, antique shops, and boutiques to hip brunch spots, a microbrewery, and a taproom. The B-Line, northern Kentucky’s self-guided bourbon trail, brings bourbon aficionados to Three Spirits Tavern, an adorable gathering space with a perfectly crafted Old Fashioned.

Winchester
Population: 19,071

Winchester is the Birthplace of Beer Cheese. Yes, that ooey-gooey dip and delicacy is a Kentucky original born in the land of Daniel Boone. If fact, one of the 15 stops on Winchester’s Beer Cheese Trail, the Pilot View Mini Mart, is located not far from where Boone got his first look at Kentucky from atop Pilot Knob. Don’t miss the annual Beer Cheese Festival in June. It’s the world’s only festival dedicated to the celebration of this cheesy concoction.

Beyond cheese, Winchester has a lovely Historic Downtown District full of shops and restaurants. Winchester is a jumping-off point to the Red River Gorge Geological Area in the Daniel Boone National Forest and nearby Fort Boonesborough State Park.

Paris
Population: 10,209

An Eiffel Tower, pastries at the Farmers Market, a sidewalk café—or in this case, trackside at the Trackside Restaurant and Bourbon Bar—sound like Paris? Kentucky’s own ville de lumière has a charming downtown surrounded by the horse farms of Bourbon County.

Stroll Main Street and stop for a photo-op at the 20-foot-tall Eiffel Tower. Visit Secretariat Park to see a life-size bronze statue and the world’s largest mural of “Big Red,” considered to be the greatest racehorse in history. Overnight in a penthouse suite atop the world’s tallest three-story building (per Ripley’s Believe It or Not!) at the Paradise Inn.

At Hartfield & Company, go behind the scenes at Bourbon County’s first craft distillery since Prohibition. Tour Claiborne Farm (the final resting place of Secretariat) and see other renowned horse farms.

Danville
Population: 17,000

The birthplace of Kentucky is home to the three-acre Constitution Square Historic Site, an open-air museum with frontier log buildings. From this historic park to the beautiful campus at Centre College nearby to the recent multimillion-dollar Main Street streetscape project, it is obvious this town takes pride in what makes it unique.

Danville is full of treasures. Pioneer Playhouse, Kentucky’s oldest outdoor theater, is about to enter its 75th season. It’s one of the oldest continuously operated summer stock theaters in the United States. The Great American Dollhouse Museum is a miniatures wonderland featuring more than 200 displays. Family-owned Burke’s Bakery has been satisfying sweet tooths with homemade bread, donuts, pastries, and cookies for a full century. In fall 2023, the GLASS National Art Museum will also open downtown, featuring the artistry and history of glass blowing.

Horse Cave
Population: 2,221

Tiny Horse Cave sits atop Hidden River Cave, the world’s longest underground suspension bridge that provides access to Sunset Dome. The cave’s entrance is located directly off Main Street, a National Register of Commercial Places Historic District. Enter through the American Cave Museum, where you can learn the story of the cave’s recovery, its geology, and the history of Cave Wars.

Pet kangaroos at Kentucky Down Under Adventure Zoo and feed camels at Dutch Country Safari Park. Spot horse-drawn buggies clip-clopping along rural roads where a fast-growing Amish population thrives. Munch on melt-in-your-mouth fried pies at Farmwald’s Restaurant and Bakery. Crawl into a Conestoga wagon or climb into the treetops for cozy overnights in a treehouse at Horse Cave KOA Holiday.

Berea
Population: 15,924

Come to the Folk Art and Craft Capital of Kentucky to experience spoonbread, a melt-in-your-mouth Southern cornmeal souffle served at the historic Boone Tavern Hotel and Restaurant. Stay for the history, culture, arts, live studio artist demonstrations, hands-on workshops, and LearnShop classes held annually in July, November, and December where you can learn everything from jewelry making to painting to woodworking.

Berea has one-of-a-kind shopping and dining experiences, like the Kentucky Artisan Center, displaying the artworks of more than 850 Kentucky artisans, and the new Honeysuckle Dining and Bourbon House, tucked inside the former Churchill Weavers building. Hike the Pinnacles in the Berea College Forest—considered among the very best hikes in Kentucky. The annual Christmas in the Village, with tree lighting, storytelling, hot cocoa, and marshmallow roasting, is straight out of a “Hallmark” movie.

Pikeville
Population: 7,327

Despite being known as the site of the bloody Hatfield and McCoy feud, Pikeville is a peaceful and picturesque community set against a dramatic Appalachian Mountain backdrop.

At the Visitors Center, pick up the audio driving tour—a wonderfully immersive journey into Hatfield and McCoy history that unspools as you experience the authentic feud sites. Dine at Cherico’s Ristorante, set in the former home of McCoy family patriarch, Randolph, and his wife, Sarah.

Downtown’s Appalachian Center for the Arts showcases Pikeville’s rich heritage and creativity, and the local outdoor music stage rocks with monthly Main Street Live! performances. High above town, the Pikeville Cut-Through provides sweeping views of the valley below.

Bardstown
Population: 13,621

The long-lived, eleven distilleries in and around Bardstown helped the town earn its nickname as the Bourbon Capital of the World. Here you’ll find the oldest western stagecoach stop in America at Old Talbott Tavern alongside more distilleries than you can shake a stave at, including heritage brands Heaven Hill Distillery, Four Roses, and the Bardstown Bourbon Company.

Independently owned boutiques and restaurants dot the square. A village of 18th and 19th-century log houses add charm to Museum Row which houses two Civil War museums. The lushly landscaped My Old Kentucky Home State Park is the backdrop for the 200-year-old grand manse, Federal Hill, where more than 75 percent of the belongings are original to the property. It’s also the site of the summertime outdoor Broadway musical, “The Stephen Foster Story.”

La Grange
Population: 10,183

The Miss Manners of small towns, La Grange is the Kindness Capital of Kentucky and the only town in the U.S. with a freight train running on its historic Main Street. The train may be rumbly, but it only adds to the Mayberry-esque ambiance of a quaint downtown awash in yesteryear colors and lined with boutiques, restaurants, wine bars, galleries, and museums.

Pop into One Nineteen Main Street and watch the trains roll past. With board games decorating the walls and signature specialties like fried green tomatoes, hot chicken livers topped with tobacco onions and pimento cheese, and country ham quesadillas on the menu, One Nineteen is full-on nostalgia and authentic Kentucky.

La Grange is located in Oldham County, the Farm Tour Capital of Kentucky, which offers up-close and hands-on experiences at 15 different farms, including thoroughbred and dairy farms.

Maysville
Population: 8,584

This picturesque town on the banks of the Ohio River has a downtown known for historic architecture, arts and culture, and waterside dining, including Caproni’s on the River—a favorite of the Clooney family (yes, those Clooneys).

It is home to the Kathleen Savage Browning Miniatures Collection at the Kentucky Gateway Museum Center, the world’s largest private collection of miniatures. See miniature houses, room boxes, and vignettes—each exquisitely accessorized in the tiniest details, including a re-creation of Spencer House, the magnificent eighteenth-century aristocratic palace and ancestral home of Princess Diana.

Visit the Old Washington Historic District, a 1700s village crowded with local shops and museums. Delve into the history of one of Kentucky’s earliest settlements and its ties to Underground Railroad history.

Greenville
Population: 4,380

This idyllic small town has one of the most beautiful courthouses in Kentucky. The century-old Beaux-Arts style building, topped by the state’s second-largest bell tower dome, anchors a town square. Here you’ll find bustling independently owned shops, eateries, and arts venues, including the Muhlenberg Community Theatre, located inside the former Palace Theatre.

One of Greenville’s shops, the House of Onyx, is the world’s largest wholesale gemstone dealer. Exploring this hidden treasure is like visiting a museum, the showroom is a veritable gallery of sparkle with diamonds, rubies, sapphires, silver, gold, and more. Another shop, the Screen Door, is a homey hodgepodge of primitives.

Nearby adventure awaits in Lake Malone State Park where the beloved Big Twigs family of sculpture giants live.

Hodgenville
Population 3,392

Hodgenville is the hometown of America’s 16th president. Abraham Lincoln was born here in 1809. See the Symbolic Cabin in the Memorial Building at the Abraham Lincoln Birthplace National Historical Park as well as Lincoln’s Boyhood Home at Knob Creek.

Visit the colorful and richly detailed dioramas at the Lincoln Museum downtown that narrate key chapters in Lincoln’s Life, from his Kentucky cabin years to his assassination at Ford’s Theatre. Outside, two statues of the Rail-Splitter bookend a charming parkland area within the town square.

Grab a burger at local favorite Laha’s Red Castle or a pound or three of famous fudge from the Sweet Shoppe and Dessert Café. Take a hayride to the pumpkin patch at Hinton’s Orchard. Don’t miss October’s Lincoln Days, a two-day festival overrun with dozens of Lincoln lookalikes.

Augusta
Population: 1,108

This scenic river town is steward to the world’s largest collection of “White Christmas” memorabilia—props, scripts, photographs, and costumes seen in this beloved 1954 classic holiday musical. See them at the Rosemary Clooney House, the former home-turned-museum of the legendary singer who lived here for 20 years.

Grab coffee at the Augusta General Store with its old-timey atmosphere and poke around for antiques and unique gifts. Linger over dinner at the iconic Beehive Tavern while watching river traffic; you may even spot the arrival of one of the American Queen Voyages paddlewheel boats. Tour Augusta Distillery, home of the “World’s Best Bourbon,” and sip bourbon barrel-aged wine at historic Baker-Bird Winery—the only winery to have survived a Civil War Battle.