8 Quirkiest Kentucky Towns To Visit In 2025

The home of offbeat music and off-color grass, Kentucky is already a quirky state. But underneath its bluegrass are even weirder natural wonders ranging from weather-predicting worms to mammoth caves, while behind its bluegrass music are bizarre festivals for everything from fried chicken to possums to a weed/bacon dish called poke sallet. Learn where to find these natural and cultural oddities and how to blend them into an unusual 2025 vacation.

Beattyville

If you missed Groundhog Day in February, visit Beattyville in October to see a different animal oracle. The woolly worm, AKA woolly bear caterpillar, supposedly forecasts the weather with its colored bands. Brown means a mild winter. Black means a harsh winter. Beattyville keeps this folklore fresh with the Woolly Worm Festival, a multi-day extravaganza held since 1988.

In contrast to pint-sized predictions, the festival welcomes tens of thousands of humans who eat, drink, dance, cruise, play, sing, and line Main Street for the Woolly Worm Festival Parade. The 2025 edition is to run from Friday, October 24, to Sunday, October 26. In between woolly festivities, search the adjacent Daniel Boone National Forest for woolly worms in their natural habitat. Let them be, though. The Woolly Worm Festival causes enough chaos for those little critters.

Fort Mitchell

Fort Mitchell is full of dummies. That is no pejorative. Rather, this small Kentucky city boasts the Vent Haven Museum, "The World's Only Museum Dedicated to Ventriloquism." Over 1,000 dummies and other artifacts of ventriloquism can be seen by appointment until fall.

Further, the Vent Haven Museum annually hosts the Dummy Run, a 5K run/walk for cash prizes scheduled for Sunday, June 29, 2025, and the Vent Haven International Ventriloquist ConVENTion, where hundreds of ventriloquists and fans gather for several days of voice-throwing fun. 2025's ConVENTion is scheduled for July 16, 17, 18, and 19.

Harlan

Harlan County is a notorious region in the Kentucky Appalachians known for rugged terrain, backwoods culture, alcohol prohibition, and mining conflicts of the kind depicted in the Oscar-winning documentary Harlan County, USA. Its county seat is Harlan, which rolls many such Appalachian staples into one unique annual festival. Named for a regional dish of weeds and bacon grease that is served at the event, the Poke Sallet Festival spans three days of traditional food, music, drinks, and activities like the Sue Ford Memorial Car Show and Poke Sallet Idol. Sadly, 2025's edition just passed in early June, but if you venture to nearby Cumberland on Saturday, September 6, you can catch another Harlan County oddity: PossumFest. This one celebrates "everyone’s favorite trash cat."

Cave City

You can have as much fun under Kentucky as you can above. The state claims over 5,000 caves, including the longest cave system in the world. Aptly called Mammoth Cave, this 400-plus-mile system is partly preserved by Mammoth Cave National Park and sufficiently supplied by Cave City.

Tourists funnel through town to explore Mammoth Cave, which offers a variety of tours from the Domes & Dripstones Cave Tour to the Historic Cave Tour to the River Styx Cave Tour to the Gothic Avenue Cave Tour. But if you do not want to slay the Mammoth, conquer a smaller cave called Crystal Onyx or above-ground oddities like Dinosaur World and the Mammoth Cave Wildlife Museum.

Pleasant Hill

Outside of modern Lexington sits a village that is absolutely shaking with historic quirkiness. Dubbed the Shaker Village of Pleasant Hill (AKA Shakertown), this 3,000-acre property preserves a once-thriving commune run by Shakers, members of a radical Christian sect known for hysterical worship. Over a century after the commune dissolved, you can worship like a Shaker at the Meeting House (c. 1820), shop like a Shaker at the Carpenters' Shop (c. 1815), eat like a Shaker at The Trustees’ Table (c. 1839), and sleep like a Shaker at the West Family Dwelling (c. 1821). Moreover, you can attend such recurring events as Goat Yoga, Music on the Lawn, and Fresh Food Adventures, ranging from "Farm Feast" on Saturday, July 26, to "Quail Dinner" on Saturday, November 15.

West Point

According to north-central Kentucky folklore, Leah Smock of Battletown became, in 1840, the last American burned to death for being a "witch." Almost two centuries later, locals celebrate Leah Smock with a yearly festival. Originally called the Battletown Witch Festival, it is now under a new name: Kentucky Folklore Festival. Smock will still be celebrated alongside other local cryptids. While attending the fest on Saturday, October 25, see additional West Point wonders like Tioga Falls, the Fort Duffield Park & Civil War Historic Site, and the edge of Fort Knox.

London

If you are too chicken for West Point's witch fest, head to London, Kentucky, for the World Chicken Festival. Established in 1990, this egg-cellent event honors Kentucky's fried chicken heritage, especially KFC. Colonel Sanders marinated the company in nearby North Corbin, which preserves his original restaurant as the Sanders Cafe & Museum. Festivalgoers can visit the museum, listen to music, join competitions like Chicken Trickin' Trivia or the Colonel Harland Sanders Look-a-Like Contest, and eat one of 120,000-plus fried chicken meals that have been cooked in the World’s Largest Stainless Steel Skillet since 1992. The 2025 World Chicken Festival is set to run from Thursday, September 25, to Sunday, September 28.

Clermont

Clermont is a tiny unincorporated community with two vast but vastly different attractions. First is the James B. Beam Distilling Co., a 420-plus-acre property that hosts recurring events like the Shutdown Distillery Tour & Tasting from late June to late July and special events like the Smoked BBQ Dinner Feastival set for Tuesday, October 7. Second is the Bernheim Forest and Arboretum, a 16,000-plus-acre preserve with "a million things to see and do," including walking among the sculpted Forest Giants, joining excursions like Firefly Friday and the Full Moon Hike, and attending the annual electric evening festival CONNECT on Saturday, August 16. Mix whiskey and whimsy in Clermont, Kentucky.

Though 2025 is almost half over, many of Kentucky's quirkiest events occur in the back half. Fort Mitchell's Dummy Run runs in late June; Pleasant Hill's Farm Feast is set for July 26; Clermont's CONNECT fest should connect on August 16; London's Chicken Festival is slated for late September; and Beattyville's Woolly Worm Festival is predicted for late October. See these and Kentucky's non-time-sensitive oddities throughout the rest of the year.