You've heard about the distilleries, antebellum homes, and bluegrass pastures along the Bourbon Trail — south of Louisville and west of Lexington. But you probably didn't know this route is ripe for biking. You can ride hard on Kentucky's hilly country roads and then unwind at some of America's best historic hotels and bars. Take four days to explore Louisville, Bardstown, a handful of distilleries, and the Kentucky countryside. Just don't overdo the evenings: Come morning, you'll be in the saddle.
For your first full day, explore the state's biggest, most bike-friendly city. Be sure to drop in for a highball at The Seelbach hotel, referenced in The Great Gatsby and frequented by Al Capone. Then head over to Louisville's other historically significant hotel, The Brown, and try the sandwich they made famous: the Hot Brown, which piles turkey, bacon, tomato, and Mornay sauce on toasted bread. If you didn't bring your own bike, take a taxi to Scheller's Fitness & Cycling and rent one, then get acquainted with the Louisville Loop, a 100-mile alt-transportation project within city limits that's now under construction (and 40 percent complete). Head northeast on the waterfront roads for 20 miles to Captain's Quarters, a waterfront seafood joint with river views, buckets of shrimp, and fish tacos. Sleep at the chic, newly acclaimed 21c Museum Hotel, where, through July, contemporary Cuban paintings line the walls. Before turning in, get a cheese plate and cocktail at Proof on Main's bar.
2. Tour Old Kentucky
On day two, head south into the heart of bourbon country by way of the Old Kentucky Home Tour, a popular 55-mile ride that connects Louisville and Bardstown but avoids the traffic. This daylong ride gains 1,483 feet as it rolls past picket fences and grassy fields and through small towns.
For two nights make a home in the self-proclaimed “bourbon capital of the world,” a bike ride away from the three distilleries you'll soon be visiting. Stay in an old Kentucky home complete with wine bar, at the Rosemark Haven, a bed-and-breakfast that's less than a mile north of town. Be sure to sit down for the veal rollatini at Circa and, later, a drink at The Old Talbott Tavern, where the locals hang out.
4. Distilleries by Bike
If you're ready to ride 68 miles, you can hit Jim Beam, Maker's Mark, and Evan Williams distilleries all on day three. T. Jeremiah Beam's home and distillery are 15 miles north of Bardstown, while Evan Williams is just a mile from town, and en route to Maker's Mark, another 18 miles south. After a day of tasting, grab a bite at Maker's Toll Gate Cafe. Rest up in Bardstown, and ride back on day four.