Drive 118.6 miles • 2 hours, 22 minutes

See riders sitting tall in the saddle at Churchill Down Downs or go beneath the bluegrass to witness subterranean wonders. Leave room for a classic sandwich and an ample glass of bourbon while you’re at it.

1. Louisville

Starting Point • Entertainment, Food, History, Sports

Hungry? Try the Louisville classic, the “Hot Brown Sandwich,” first concocted at the city’s Brown Hotel. Sports is on tap, too: Check out Churchill Downs and the Kentucky Derby Museum, then swing by the Louisville Slugger Museum & Factory and the Muhammad Ali Center. Play great golf courses like Valhalla and Big Spring, or bring the kids to your choice of four amusement parks, six culinary tours, 22 performing arts venues and 28 historic sites including the Old Louisville Neighborhood.

2. Elizabethtown

44.8 miles, 55 minutes • Food, History

Are you over 21 and have a designated driver? Then you might want to sip some of the world’s finest bourbons on Kentucky’s famous Bourbon Trail as you visit the many distilleries in the Elizabethtown area. Boozing aside, there’s a lot to do in Elizabethtown. The Coca-Cola Museum’s packed with Coke memorabilia, while Swope’s Car Museum displays great vintage rides. Hardin County History Museum has a great Civil War display; take a quick drive to see Abe Lincoln’s birthplace, boyhood home and the quintessential Lincoln Museum.

3. Cave City

43.2 miles, 49 minutes • Food, Nature, Outdoor Recreation, Quirky, Sports

Cave City’s the Cave Capital of Kentucky, home of Mammoth Cave National Park; 53,000 acres of the world’s longest cave system. Explore caverns studded with stalactites, stalagmites, travertine dams, 4,000 passages, 400 trails and more. There are eight caves in all. Back above ground, you’ve gotta see Dinosaur World’s life-size replicas and whip down a zip line or an alpine slide. Afterward, feed your sweet tooth at Chaser’s Chocolate—you deserve it.

4. Bowling Green

30.6 miles, 39 minutes • Entertainment, Food, History, Nature, Sports

The famous GM Corvette is built here—visit the factory and see more than 70 classic Corvettes at the National Corvette Museum. Cheer as drivers burn rubber at Beech Bend Raceway, America’s oldest quarter-mile drag strip. Take an underground boat tour at Lost River Cave, or ride the Kentucky Rumbler roller coaster (and 40 more rides) at Beech Bend Amusement Park. How about agrotourism? Visit local family farms for some homemade ice cream, fresh fruits and family fun.