Did you know the US commercial wine industry began in Kentucky at First Vineyard Winery in Nicholasville? (Take that, Napa Valley!) And that Bigfoot is frequently sighted in the Red River Gorge area? The Bigfoot Festival, held in Stanton, pays tribute to the wily cryptid—as does a Somerset museum called the Paranormal Roadtripper’s Nightmare Gallery.

Cross a bridge suspended over sharks at Newport Aquarium and one swaying high above a river at Hidden River Cave. Meet the Tin Man in Clermont. (He’s proving there’s no place like Kentucky in Bernheim Forest.) Sleep in a jail cell at the Jailer’s Inn or in the hotel that inspired F. Scott Fitzgerald to pen the Great American Novel at the historic Seelbach Hilton.

These are among the 100 things handpicked by travel writer Kathy Witt—superlative, standout experiences that will take you all over the Bluegrass in search of memory-making adventures, like shopping among floating eyeballs in MainStrasse Village at Hail-Records & Oddities, stepping in as a second in a duel at the Sandford Duncan Inn, and crooning tunes by the country’s first pop star at The Stephen Foster Story musical production.