7 Coolest Towns in Kentucky for a Summer Vacation in 2024

Every year is a great year to visit Kentucky, but 2024 is especially good timing. This year, Kentucky State Parks celebrates its 100th anniversary with a series of events that showcase the incredible (and very cool) beauty of the bluegrass state. It’s also the 25th anniversary of the Kentucky Bourbon Trail, a legendary route covering historic sites, country towns, inviting eateries, and — of course — award-winning distilleries. Even in a quiet year, Kentucky is one of America’s coolest states. The home of blues, BBQ, and Bluegrass is bound to have a little swagger. Whether riding horseback on rustic trails, sipping Kentucky moonshine, or watching steamboats drift down the Ohio River, this is a vacation you’ll remember long after you've unpacked your suitcase.

Augusta

Augusta is a charming river town on the banks of the Ohio River. The town was first given its charter in 1797, making it one of the oldest in Kentucky. You can see echoes of Augusta’s long history almost everywhere you look in town, but sites of particular interest include the 1811 jail, Underground Railroad safehouses Payne House and White Hall, and Cemetery Hill, the site of the 1862 Battle of Augusta. Augusta is also home to one of the oldest ferry services on the Ohio River, operating since 1798. You can ride the Jenny Ann daily throughout the summer to catch the river’s cool breezes and gorgeous views. Augusta has plenty of Kentucky charm, but the town claims some Hollywood stardust, too. You can learn about its famous residents at the Rosemary Clooney Museum, the former home of the singer and movie star.

Slade

Kentucky is home to over 2,000 natural arches — the most of any state east of the Mississippi River. See the most famous at the Natural Bridge State Park near the tiny town of Slade. The Natural Bridge is a jaw-dropping sandstone arch stretching more than 75 feet long and 65 feet high. Explore the arch from the sky courtesy of the Sky Lift which floats above the forest canopy to give incredible views of the ridge below. There’s another natural wonder near Slade that attracts outdoor adventurers to the town. The Red River Gorge is known for its world-class climbing, biking, and hiking. With zip lines, kayaking tours, and bird-watching, there’s something for everyone in the family at this hidden gem. You can even stay in a treehouse for the ultimate cool vacation. These aren’t your typical backwoods huts either. Choose from the Observatory treehouse, with sweeping views over the gorge and a hammock lounge, or the Tradewinds Treehouse, which boasts a slide to the ground and a hot tub.

Cave City

As you can probably guess from the name, the action in Cave City happens underground. This small town is the gateway to Mammoth Cave National Park, the world’s longest-known cave system. There are over 400 miles of underground passageways in the park which you can explore by bike, kayak, hiking, or on a ranger-led tour. Stay after dark for stunning stargazing. On a clear night, you might just see the International Space Station! There’s more to Cave City than caves, however. Take the kids to Dinosaur World for a very cool vacation experience — wandering among life-sized dinosaurs, riding mammoths, and panning for gemstones.

Maysville

Maysville is a picturesque town in Northern Kentucky known for its history and hospitality. The town has two historic districts, downtown and a 1780s frontier village on the outskirts of town known as Old Washington. The latter traces the history of Kentucky from its rural beginnings in pioneer log cabins to grandiose brick homes and Georgian townhouses. Downtown Maysville is a hub of arts and entertainment with funky boutique shops, galleries, and charming eateries where you can sample the local specialty, goetta — a dish of sausage and steel-cut oats. While in town, be sure to visit the Old Pogue Distillery, one of the stops on the Kentucky Bourbon Trail. The distillery is housed in the 1845 Pogue family home along with a gift shop and bourbon museum. Tours are available by appointment so you’ll need to reserve in advance.

Clermont

Clermont, south of Louisville, is the only place in Kentucky where you can spend the day hanging out with forest giants. The Bernheim Arboretum and Forest near town contains three massive human-like structures made from repurposed and natural materials. The striking sculptures, named Mama Loumari, Little Nis, and Little Elina, are within walking distance of each other on a two-mile roundtrip loop through the forest. Enjoy a bird’s eye view of the forest with a canopy tree walk, 75 feet above the forest floor. Visit Bernheim in August for the annual CONNECT festival, a stunning evening show of interactive art exhibits that light up the forest. After a day in the forest, slake your thirst at the Jim Beam American Stillhouse, where seven generations of the Beam family have honed their craft. Not a whiskey drinker? No worries! The Forest Edge Winery is also well worth a visit with regular tasting events of its award-winning vintages.

Rosine

Rosine is a tiny community famous for being the birthplace of ‘the father of bluegrass,’ legendary musician Bill Munroe. Every summer, the Rosine Barn Jamboree plays tribute to this local icon with unforgettable evenings under the stars as the historic barn comes alive every Friday night with jumping bluegrass, country, and gospel music. True fans can also make the pilgrimage to Bill Munroe’s Home Place and Museum, which dives into the history of the bluegrass genre, Rosine, and the musician himself. Nearby is Uncle Pen’s Cabin. Now a small museum, this rustic cabin was once home to Pendleton Vandiver, one of Kentucky’s best fiddle players and Munroe’s uncle and playing partner.

Dawson Springs

Dawson Springs in Western Kentucky is the state’s first certified Trail Town. This designation is given to communities with an abundance of natural trails and scenic features, perfect for outdoor adventurers. Located in the Pennyrile region, the town is close to Pennyrile State Forest, where you’ll find some of Kentucky’s best equine trails winding over sandstone bluffs and alongside glittering streams. This area also boasts the Tradewater River, one of the largest in the state, and beautiful Lake Beshear, both of which are perfect spots for lazy summer boating or a fun canoe trip. Back in town, learn the history of this scenic area, known as a wellness resort since the early 1900s, at the Dawson Springs Museum and Art Centre, which is housed in the Old Commercial Bank, built in 1907.

Cool Kentucky Communities

The Kentucky Heritage Council celebrates a landmark this year, the 45th anniversary of their Main Street program, an initiative launched to preserve the history and heritage of the state’s vibrant downtowns. Kentucky knows it has something special, and this is a state that’s happy to share, showing off its many natural and historic attractions to visitors. A blend of southern charm and midwestern grit, Kentucky contains plenty of cool small towns to match its cool landscape — places where you can soak up the spirit and style of this unique state.