Trip Details

While there are many different ways to visit Kentucky, there may be no better way than cycling through the lush landscape of rolling hills, rambling Thoroughbred farms and, of course, the golden rye fields which supply the state’s finest distilleries. Over five days, pedal more than 125 miles through this gorgeous country with stops at all the best spots along the way.

Arrive and head straight to A Storybook Inn for a night of rest before the tour begins the next morning bright and early. Take a long soak in the whirlpool tub, loosening up your muscles before tucking yourself into bed. A Storybook Inn is just the first of three lodging locations you’ll visit on your tour, which also includes one night at the Shaker Village Inn, a national historic landmark, and the 21C Museum Hotel, a contemporary boutique hotel and art museum located in the middle of downtown Lexington.

Day one begins at Keeneland Horse Track, where you’ll take a tour of the internationally renowned racecourse and learn about the history and tradition of the horse racing industry. After the tour, your ride begins here, where you’ll quickly be immersed in the countryside’s rolling hills as you make your way towards the days end and the  trip’s first distillery, Woodford Reserve. Enjoy a tasting before an optional eight-mile ride home — a support vehicle is available along the entirety of the trip for anyone who feels like a rest.

The next morning, take a walking tour of Buffalo Trace before a 36-mile ride alongside Elkhorn Creek. Don’t miss your opportunity to try the Honey Bourbon ice cream at Wallace Station before returning for your final night at A Storybook Inn. The next day, a 33-mile ride will take you to Shaker Village, where you’ll have plenty of time to explore the historic grounds before setting off on a scenic riverboat cruise on the Kentucky River. 

The final two days of the trip, ride through the heart of bourbon country with stops at Four Roses and Town Branch Distilleries as well as Claiborne Farm, the “Birthplace of Champions” and final resting place of Triple Crown winner Secretariat. Enjoy Kentucky Fried Pickles during your final lunch, before hanging up your bike for the last time. While we do recommend some training ahead of the trip to make the experience more enjoyable, even inexperienced cyclists will find this once-in-a-lifetime tour as rewarding as a blanket of roses.