11 Kentucky Towns With Unforgettable Main Streets
A thriving Main Street (or main street, as the case may be) offers locals a place to gather and visitors a look at the personality of a community. While the actual “main” street might have a different name, it is a central district, often historic, and always creative. Old buildings, new life, and the realized dreams of small business owners, chefs, and artisans often pave the way to something bigger and better than the sum of its parts. These 11 Kentucky towns with unforgettable main streets invite visitors to come back again and again.
Paducah
Known worldwide as a center for artisan quilting, Paducah is a UNESCO Creative City of Crafts and Folk Art, but that’s just the start of a visit to this thriving community. Visitors flock to the National Quilt Museum and AQS QuiltWeek, but the historic downtown area is not to be missed. Architectural Digest recognized it as one of the country’s most beautiful and distinctive Main Streets. For Kentucky bourbon, Silent Brigade Distillery produces its wares from local ingredients and makes the first bourbon from Paducah since the days of Prohibition. And stop by Stella’s Tavern for an inspired dinner menu in a historic setting. Creativity abounds in Paducah, with The Carson Center for the Performing Arts serving as home to Broadway tours, the Paducah Symphony Orchestra and more, and the “Wall to Wall” murals series offering a visual celebration of the city through more than 50 panoramic murals. Nearby Market House Square includes The Art Guild of Paducah Gallery where visitors can buy a handcrafted work to take home.
Pikeville
Pikeville’s downtown area is indeed more than just Main Street, but that is a great anchor for exploring this historic town. Fuel up at surprise spots like Chirico's Ristorante, featuring authentic Italian cuisine and located in a historical landmark of the Hatfield-McCoy Feud. The city leans into the history of that famous feud and its lessons about holding a grudge at points off the Main Street hub like Dueling Barrels Brewery and Distillery, where the grownups can taste local craft beer and Kentucky moonshine, and dine at Pearse's Place upstairs. For a stop for all ages, check out a show at The App, the Appalachian Center for the Arts, with its full slate of stage productions.
Covington
Head to Germany without ever leaving Northern Kentucky at Covington’s MainStrasse Village. Just across the historic John A. Roebling Suspension Bridge and the Ohio River from Cincinnati, Ohio, Covington’s MainStrasse is where visitors will find food, music and a full calendar of festivals, including Oktoberfest, with German food and beer, and Maifest, complete with maypole dancing. MainStrasse was once the starting point of the World's Longest Yard Sale and it remains a part of the event that spans six states. Enjoy the village atmosphere with a stop at Crafts & Vines for small plates, wine and local brews.
Harlan
Explore Appalachian history in Harlan, where you can tour an old mine and learn about life in the Cumberland Gap. But when you’re ready to stroll, take in Main Street, starting at Harlan Center, site of a wide range of events and home to the Harlan Tourist & Convention Commission, where you can learn about a downtown walking tour. Stop for breakfast or lunch at Moonbow Tipple Coffee and Sweets, located in Main Street’s historic Buttermore Building. And shop ‘til you drop for vintage pieces and local art at Sassy Trash or unique souvenirs of your visit at Henry's Souvenirs and Gifts.
Bardstown
Bardstown, Kentucky’s second oldest city, has a dedicated Main Street Program focused on the community’s downtown. Free digital walking tours are available. Visitors can find unique local spots like Scout and Scholar Brewing Company, which offers a beautiful outdoor dining space, and the Old Talbott Tavern, built in 1779. The setting exudes charm and you can’t miss historic areas like the town square. Throughout, creativity abounds and bridges the old with the new. Bourbon is just a stone’s throw away in this distillers haven. You can choose from more than 400 varieties at Volstead Bourbon Lounge.
La Grange
You can’t miss the train in La Grange — it runs down the middle of Main Street — but be sure to visit the La Grange Train Museum to satisfy train enthusiasts of all ages. Get creative on Main Street, with stops like Gallery 104, which features more than 25 regional artists. Prefer to create your own art? Try stopping at Friends and Fiber, a local yarn shop that is all about connection. Slow your day with food and a view of that Main Street train route at One Nineteen West Main, offering American and New Southern cuisine.
Franklin
While it is not on Main Street, Franklin does boast a Fork in the Road, the tallest fork sculpture in Kentucky, which is surely worth a stop before heading downtown. Once in the historic district, Main Street features The Gallery on the Square, a nonprofit art haven that offers classes and much more. Next door, find the Mustard Seed Market with a little of everything for shoppers, from vintage items to jewelry and gifts. Visit Willow Hill Marketplace for clothing and gifts, as well as The Candle Bar where visitors can attend a DIY candle pouring workshop.
London
It likely isn’t the first London to come to mind, but London, Kentucky, is shaping its own identity in a welcoming downtown. On Main Street, look for unique events like a Valentine’s Day “Love Letters from London.” Businesses set up antique typewriters and invited guests to stop by and type a letter to someone special. Each spring, the town hosts the Redbud Ride, a cycling event with options for beginners to seasoned athletes. Fuel your summer afternoon with a stop for sweet treats at Moody Cows, where the motto is “Lousy company. Mediocre Entertainment. Insanely Good Treats.” End the day with dinner at Local Honey to try local farm fresh ingredients.
Shelbyville
Located in Shelby County, Shelbyville’s Historic Downtown is bustling with character. Start your day with brunch on the porch at Bell House Restaurant and walk down Main Street to shop at unique stops like Reclaimed on Main for antiques and vintage items or Stacey’s Simple Stuff, which offers farmhouse décor and more. Ready for dinner? Try La Cocina de Mamá Mexican Cuisine, featuring creative family recipes. Round out the day with a performance at the Shelby County Community Theatre. While in Shelbyville, don’t miss the local stops on Kentucky Black Trailblazers Augmented Reality Experience, a new, immersive journey through Black history that extends across the state.
Elizabethtown
Elizabethtown or “E-town” boasts a postcard-beautiful historic downtown and a true public square surrounded by historic buildings that are now home to hot spots like Vibe Coffee, where visitors can try unexpected items like a Honey Sage Latte, and The Original Impellizzeri's, home of craft beer and specialty pizzas, located in the historic Stewart Opry House. To cool off on a hot summer afternoon, get creative at Kuddy's Sips and Sweets, a “soda mixology experience” that takes fizzy drinks to new heights. Take it easy at Social on Main, for duckpin bowling, a food hall featuring wood-fired pizza, ramen, and a street-style taqueria, plus a tap wall with a wide selection of beer. Central seating invites connection, so be sure to meet the locals while you visit.
Beattyville
Beattyville is just 20 minutes south of the Red River Gorge and Natural Bridge State Park, making it an ideal place to recover from outdoor adventures while experiencing local flavor and supporting small businesses. Try Los Two Brothers for Mexican cuisine or stop by Brenda’s BBQ Smoke Shack for local barbecue. Nearby, the Bobcat Dairy Bar serves hand-dipped ice cream and boasts a secret goulash recipe that has been on the menu for more than 65 years. Each October, the Woolly Worm Festival is a true community event, with a parade, a car show, and a full weekend of music and family fun.
No matter where you travel, making a stop on Main Street and asking a local for a recommendation for the best of the best makes a visit something special and unforgettable. Visiting these 11 Kentucky towns with unforgettable main streets might lead you to a memorable meal, a vintage find, or a connection to a community that lasts long after the trip ends. And it is a way to support small businesses and invest in the work and dreams of creators and artisans, along with the visionaries who make sure Main Streets thrive for years to come.
