Weird & Wonderful Kentucky Roadside Attractions: Road Trip Stops You Can’t Miss
Kentucky has no shortage of weird roadside attractions, small-town museums, and offbeat destinations that make every Kentucky road trip unforgettable. In the pre-interstate days, these quirky spots gave travelers a reason to pull over, stretch their legs, and discover something unexpected. Many are still thriving, thanks to locals who keep the traditions alive.
Kentucky filmmaker Steven Middleton set out to document these gems in his films Commonwealth Curiosities (Volumes 1 & 2), both aired on KET. His work captures the state’s strangest museums, monuments, and sideshow-worthy attractions. If you love weird Kentucky travel, roadside Americana, or planning unique road trip ideas, here are 11 attractions you need to see for yourself.
Top 11 Weird Roadside Attractions in Kentucky
Kentucky Reptile Zoo – Slade, KY
Home to one of the largest collections of venomous snakes in the world, the Kentucky Reptile Zoo has been featured on National Geographic and Animal Planet. It breeds snakes, extracts venom for lifesaving antivenom projects, and educates visitors about reptiles. A must-stop for both science buffs and those who love weird roadside attractions in Kentucky.
Akemon's Barbershop & Music – Paris, KY
This isn’t your ordinary barbershop. At Akemon’s Barbershop, you can get a haircut while listening to live music. Owner Joe Akemon’s family ties to Opry star Stringbean give the shop a true Kentucky musical soul. Instruments line the walls, music lessons are offered, and the vibe is pure small-town charm.
East Kentucky Museum of Mysteries – Van Lear, KY
A true sideshow stop, the Museum of Mysteries features oddities like a Fiji Mermaid, antique embalming tools, and war memorabilia. Run by David Harrington, a paranormal investigator, the museum brings curiosity and storytelling back to roadside Americana. Perfect for anyone who loves weird Kentucky legends.
Apple Valley Hillbilly Garden & Toy Land – Calvert City, KY
Created by Keith Holt, the Hillbilly Garden is a folk-art playground filled with toys, art installations, and quirky sculptures made from discarded items. From Barbie dolls to Elvis busts, this attraction is part toyland, part outsider art exhibit — a celebration of weird Kentucky creativity.
Dinosaur World – Cave City, KY
Located near Mammoth Cave, Dinosaur World is hard to miss — life-sized dinosaur statues tower over the trees along I-65. With hundreds of dinos, fossils, a museum, and picnic grounds, it’s both kid-friendly and delightfully kitschy. A must-see Kentucky roadside attraction for families.
World’s Tallest Three-Story Building – Paris, KY
This building has been baffling visitors since 1891. Known as the World’s Tallest Three-Story Building, it’s a quirky claim to fame that keeps Paris, Kentucky, on the roadside oddities map.
Northeastern Kentucky Museum – Olive Hill, KY
Founded in 1972, this small museum features fossils, Native American artifacts, and local memorabilia. The Native collection, with pottery and jewelry, makes the Northeastern Kentucky Museum a hidden-gem stop on your next Kentucky road trip.
Wooldridge Monuments – Mayfield, KY
Henry Wooldridge, a horse trader and lifelong bachelor, had sandstone and marble monuments built to depict himself, his family, and animals. Known locally as the “Monument to the Strange Procession,” the Wooldridge Monuments remain one of Kentucky’s most photographed and unusual roadside memorials.
Plan Your Kentucky Road Trip
From snake zoos to dinosaur parks, Kentucky’s roadside attractions prove that weird and wonderful Americana is alive and well. Whether you’re planning a Kentucky road trip, looking for hidden gems, or chasing weird Kentucky legends, these stops deserve a place on your map.
Inspired? Shop our Kentucky gear collection for tees, hats, and socks made for road trips across the Bluegrass State.