7 Playfully Peculiar Towns In Kentucky

There are plenty of playful ways to explore Kentucky. One is by paddling its 1,020-ish miles of commercially navigable waterways, which is fourth-most of all states according to the Kentucky Transportation Cabinet. If you would rather stick to land, take the Kentucky Bourbon Trail over hundreds of miles and possibly hundreds of drinks. Or you can get intoxicated off Kentucky oddities, stopping at towns with strange yet stimulating sights, ranging from a wigwam village to a whimsical garden and toyland to a 68,000-pound baseball bat. Choose the last route if you want more than just a playful KY vacay. Make it playfully peculiar with the following seven stops.

Cave City

Take a wild guess of what brings tourists to Cave City. You got it: dinosaurs. Sure, there is a popular nearby cave — multiple, in fact, including the world's longest cave system, Mammoth Cave — but also drawing visitors, especially families with young children, is Dinosaur World. Kids wander among hundreds of life-sized sculptures of prehistoric beings, their dino-caused transfixion providing parents with respite. Seeking more quirky distractions, they can trade replicas for real (albeit taxidermied) animals at the Mammoth Cave Wildlife Museum, which exhibits everything from leopards to bears to tigers. The Historic Wigwam Village No. 2, with its teepee-style lodgings, is an apt accommodation for such an offbeat trip.

London

When you hear "Kentucky," Kentucky Fried Chicken is bound to come to mind — and mouth. Colonel Sanders first served his signature recipe in tiny North Corbin, which, following his uber-success with KFC, turned his former roadside chicken shack into the Harland Sanders Cafe and Museum. Despite comprising a 1940s-style Sanders Cafe attached to a modern KFC by an artifact-filled lobby, it is not the finger licking-est attraction in the area. That title belongs to the World Chicken Festival, which runs each September in neighboring London. The fest features "chick-a-lympics," a chicken cook-off, hot wing eating contest, egg-drop challenge, Colonel Sanders look-a-like contest, and the World’s Largest Stainless Steel Skillet. Measuring 10 feet, 6 inches in diameter, said skillet has cooked over 120,000 fried chicken dinners since 1992.

Beattyville

Skip Groundhog Day and visit Beattyville for the Woolly Worm Festival. Rather than a shadowy subterranean rodent, this event's offbeat oracle is the woolly worm (aka woolly bear caterpillar), whose 13 body segments supposedly predict the 13 weeks of winter. Black segments mean cold weeks, while brown segments mean mild weeks. The designated forecaster is the worm that wins the woolly worm races, which join live music, vendors, a pet show, car show, and parade as in-festival festivities. Following the fest, see more strange critters in the adjacent Daniel Boone National Forest, especially at the nearby Kentucky Reptile Zoo. Then rest, refuel, and potentially find a new hobby at Miguels Pizza, a farm-to-table pizzeria that's not too far away and has become an unlikely hub for mountain climbers.

Williamstown

After suspending from landforms near Beattyville, suspend your disbelief in Williamstown. This super-small city hosts Ark Encounter, which boasts a 510-foot-long, 85-foot-wide, 51-foot-high biblically accurate replica of Noah's Ark. It is considered the "world's largest free-standing timber frame structure." Inside the ark are three decks filled with exhibits. Outside the ark are other biblically based attractions like Noah’s Village, Emzara’s Buffet, and the Ararat Ridge Zoo, not to mention Screaming Eagle Ziplines. Some passes for Ark Encounter also include the Creation Museum, which is run by the same young Earth creationist organization but sits about 45 miles away in the town of Petersburg.

Calvert City

As an Appalachian state, Kentucky crawls with Appalachian oddities. Many can be found in Harlan, particularly during the annual Poke Sallet Festival, where guests sample the titular bacon-grease-and-roadside-weeds salad while enjoying live music, car and pet shows, and the celebrated Poke Sallet Idol. More oddities can be found in Calvert City. Though outside Appalachia, Calvert City is sufficiently backwoodsy thanks to the Apple Valley Hillbilly Garden and Toyland. This intergenerational estate, now run by the grandson of the original homesteaders, displays thousands of toys and countless folk art installations. In the past, Apple Valley was a gas station, general store, diner, barber shop, zoo, campground, produce stand, distillery, apple orchard, Jim Crow defier, and allegedly a hideout for Bonnie and Clyde.

Fort Mitchell

Pair the toyland in Calvert City with the dummyland in Fort Mitchell. That is no epithet; this small city is stuffed with ventriloquist dummies. Most are housed at the Vent Haven Museum, whose slogan is "The World's Only Museum Dedicated to Ventriloquism." Besides 1,200-plus dummies from three different centuries, Vent Haven has about 1,500 books, 5,000 photos, and various other artifacts. Moreover, it annually hosts the Vent Haven International Ventriloquists' ConVENTion, which features four days of ventriloquist fare, including talks from masters of the medium like Jeff Dunham and Ronn Lucas. But that is not all. Before its ConVENTion, Vent Haven puts on the Dummy Run 5K, where you can run for, rather than from, dummies. Proceeds go to ventriloquism. Since those events happen in summer, check back for 2026's dates.

Shepherdsville

Shepherdsville is an unassuming city surrounded by strange, significant sites. To its north lies Louisville, whose Louisville Slugger Museum & Factory mesmerizes with a 120-foot, 68,000-pound bat modeled after Babe Ruth's. To its southeast sits the Bernheim Forest and Arboretum, a 16,000-plus-acre oasis, complete with an edible garden and three wooden giants (Mama Loumari and her children Little Nis and Little Elina), which you can make even more fun by imbibing at the nearby James B. Beam Distilling Co. before you go. To its west stands Fort Knox. Yes, the Fort Knox. Though civilians are obviously prohibited in sensitive areas, they are welcomed at the General George Patton Museum of Leadership, which focuses on US military history with an emphasis on the titular general.

You might be tempted to keep it classy in Kentucky, but what is the fun in that? Instead of fanning yourself at the Kentucky Derby, make a derby out of far-out attractions in far-flung towns. Regret is strong with those who miss such sights as Dinosaur World in Cave City, the World Chicken Festival in London, the Kentucky Reptile Zoo near Beattyville, Ark Encounter in Williamstown, the Apple Valley Hillbilly Garden and Toyland in Calvert City, the Vent Haven Museum in Fort Mitchell, and the Bernheim Forest and Arboretum near Shepherdsville. To avoid being jelly, visit those seven Kentucky communities during your next vacation.