Kentucky is famous for thoroughbred horses and horse racing, bourbon, and a castle. You can find the world’s only UNESCO Creative City in Kentucky, sip world-famous bourbon whiskey, and watch second-to-none horse racing, all in the Bluegrass State. If you want to explore Kentucky’s adorable small towns (typically less than 25,000 people), I’ve selected a few of my favorites in no particular order, for your consideration. My choices are based on the town’s food, culture, and scenery. Regardless of which town you go to, be on the lookout for a Hot Brown, the Kentucky state dish, that is as much comfort food as it is a thing of beauty.
Fun Fact: A strong Appalachian movement is bringing the culture of areas like Tennessee and West Virginia, to the eyes of those who aren’t familiar with it. It is particularly thrilling for this native gal.
Kentucky’s capital city should be on every traveler’s radar. Frankfort sits along the Kentucky River and has a quaint downtown area with shops, gorgeous architecture, colorful murals, and street signs denoting famous residents. I loved the colorful buildings running along both sides of the railroad. Poor Richard’s Books, Kentucky Coffeehouse Cafe, and Broadway Clay are a few shops that might interest you. Don’t miss the stunning Kentucky State Capitol building and complex.
An absolute must in Frankfort is touring and sampling Rebecca Ruth Chocolates, making melt-in-your-mouth candies and bourbon balls (it created them!) since 1919. You can also visit one of the stops on the Kentucky Bourbon Trail while you are there — Buffalo Trace. This over 200-year-old distillery is in a class of its own and offers free tours and tastings.
If you want to visit a small town in Kentucky that has accomplished something that nowhere else in the world has, that would be Paducah, a historic town with much of it included in the National Register of Historic Places.
Paducah has been a UNESCO Creative City (Crafts and Folk Art) for nearly a decade. It is also famous for quilts and often referred to as “Quilt City USA,” housing the National Quilt Museum. This is only one of the art mediums found prevalent in Paducah. You will also find locally owned boutiques, art galleries, and fantastic antique stores.
A Kentucky town on the rise is Ashland, in the eastern part of the state. Ashland’s Paramount Arts Center has musical productions, concerts, and shows. Art Alley is a great place to stroll and admire the creative artwork. Away from downtown and along the Ohio River, are gorgeous steel statues donated to Ashland in dedication to its steel contributions. Central Park is a beautiful place to walk, sit, stroll, or picnic any time of the year.
You might want to try Jim’s hot dogs while you are in town, or grab a gourmet burger from Fat Patty’s. I swear by the Raspberry Popper Burger with jalapeños, cream cheese, and a raspberry melba sauce. OMG, it is fabulous. The Mill Cafe & Bakery is a popular local eatery gaining much publicity, too, with tacos, waffles, homemade soups, and sweet treats.
A world-famous equestrian town is Shelbyville, Kentucky, the American Saddlebred Capital of the World. It is also host to the Shelbyville Horse Show. Two stops on the Kentucky Bourbon Trail are nearby, Bulleit Distilling and Jeptha Creed Distillery, both offering handcrafted spirits.
In Shelbyville, two unique offerings are the Wakefield-Scearce Galleries, home to room after room of precious collections including linens, silver, English antique furnishings, and Claudia Sanders Dinner House. Claudia, the wife of Colonel Harland Sanders (of KFC fame), and her husband opened this eatery in the late 1960s. The tasty restaurant serves sugar-cured ham, fried green tomatoes, and, of course, fried chicken. If you’d prefer something quick and easy, La Cocina de Mama is a perfect spot for tantalizing Mexican eats.
Elizabethtown, or E-Town as the locals call it, was a prosperous town in the 1800s when the Louisville and Nashville Railroad was built here. It was also made famous by the movie of the same name starring Kirsten Dunst and Orlando Bloom in 2005. A few of the movie scenes were filmed here.
This charming little Kentucky town has a handful of noteworthy restaurants, a great coffee shop, and Swope’s Cars of Yesteryear Museum, a real treat for those who love vintage automobiles and car attractions. The Brown-Pusey House, circa 1825, with Georgian and Federal architecture, is worth a look. Bowling, skydiving, and nature parks are great ways to get moving in E-Town. Stop in Vibe Coffee for a white mocha latte or Aztec mocha and grab a gourmet cookie for the road.
Murray, a college town by the Kentucky/Tennessee state line, has been voted the Friendliest Small Town in America, partially thanks to its beautiful scenery and fun attractions minutes from the Land Between the Lakes region.
Enjoy the enchanting Kentucky Lake’s plethora of outdoor activities or take in the town’s many festivals and celebrations. The Murray State Arboretum is a great place for a stroll and viewing pristine landscape. Hunting, fishing, and golf are other popular options for things to do.
Doughdaddy’s Doughnuts may not be reason enough to visit Versailles, or is it? It has been a stop on our travels for two dozen years or more. Eclairs, donuts, fritters, and long johns, to name a few, are what’s on the menu. Versailles, pronounced ver-SAYLES, is right off Martha Layne Collins BG Parkway, right beside Lexington. Versailles is horse country at its finest, with beautiful farms and minutes from the internationally renowned Keeneland race track.
Versailles is another place to check off a bourbon distillery. Woodford Reserve has been in operation since 1812. Or, you could experience a craft winery, Wildside Winery, that uses estate grapes in its production.
You can’t mention Versailles and not talk about the castle that eluded passersby for years before finally being purchased and turned into a jaw-dropping hotel. The Kentucky Castle is a hotel, restaurant, spa, and event space with two Michelin chefs on the payroll. While I haven’t personally stayed there, I’ve seen pictures from friends’ visits and it is incredible! Definitely a place to keep in mind for a special celebration or milestone.
8. Grand Rivers
Another town situated near the Land Between the Lakes region is Grand Rivers. This lovely waterfront area houses hundreds of sailboats and the famous and much-talked-about Patti’s 1880’s Settlement. Patti’s has a fantastic restaurant with a country-club-like menu that features homemade pies and desserts, salads, steaks, and the raved about pork chops. Get them one or two inches thick, topped with chutney, fruit salsa, or plain, but they are juicy and cooked to perfection at this popular eatery.
Also on Patti’s property are several boutique shops, a year-round Christmas store, mini-golf, koi pond, and beautiful gardens. You could easily spend all day in this town alone, just soaking up the scenery and enjoying the relaxing setting. Save room for a slice of coconut cake or sawdust pie that will surely satisfy your sweet tooth.
Newport, Kentucky, is across the river from downtown Cincinnati, making it a metropolitan area with loads of fun, family-friendly attractions. The best known is Newport on the Levee, where you’ll find the incredible Newport Aquarium, with excellent tanks and exhibits holding fish, sharks, rare white gators, and stingrays. Newport Aquarium also has penguins, so be prepared for a cuteness overload. You will also find some adorable shops, a movie theater, and desirable restaurants at Newport on the Levee. Tom & Chee, gourmet grilled cheeses and tomato soup is my top pick.
My favorite thing to do in Newport or Cincinnati, as well, is to take a premier 90-minute sightseeing and dinner cruise on the BB Riverboat’s Belle of Cincinnati. The boats launch from Covington Landing and sails the scenic Ohio River. Cruises start at $27, and the food is really good.
Hofbrauhaus Newport is one of my go-to restaurants, an excellent place for Bavarian dishes, including schnitzel and sausages. If you really want to be adventurous, try Hofbrauhaus’ spin on the Kentucky state dish, the Hot Brown, with smoked turkey breast and Black Forest ham served on a potato pancake, then topped with Swiss cheese, homemade Bier cheese, tomatoes, crispy bacon, and parmesan. I could barely type this without drooling.
Pro Tip: Another way of exploring the area and getting fantastic photos is by walking the Purple People Bridge that connects Newport, Kentucky, to Cincinnati, Ohio.
Welcome to Bardstown, home of My Old Kentucky Home State Park and The Stephen Foster Story musical (composer of the state song). Bardstown is also home to four distilleries: Barton 1792, Willett Distillery, Heaven Hill, and Preservation Distillery, and known as the Bourbon Capital of the World. Bardstown hosts the annual and highly-anticipated Kentucky Bourbon Festival.
Looking for food after your bourbon samplings? I loved my lunch at El Jimador downtown Bardstown. The service was attentive and friendly.