Bluegrass. Bourbon. Horse Country. Experience the understated beauty of Kentucky Bourbon Country in this day-by-day photo guide taken by our talented guest, Bob Joy.

Day 1: Ride the Legacy Trail and explore downtown Lexington:
Take your first pedal strokes through horse country on the Legacy Trail Bike Path. You’ll wind your way past the Kentucky Horse Park and into rolling fields of beautiful horse farms. Your ride ends at Evans Orchard Cider Mill, where you’ll shuttle back to Lexington to walk around downtown to do some exploring before joining your group in the bar at Lockbox for a fun social hour and dinner.

Bike Tour in Kentucky

Day 2: Tour MeadowCreek Farm and enjoy a tour and bourbon tasting at Limestone Branch Distillery:
Start your day at MeadowCreek Farm, just outside the town of Lebanon. The farm is home to several impeccably pedigreed horses with impressive wins on their resumes and you will have the chance for some up-close views of these amazing creatures! After the tour, your guides will shuttle you to Limestone Branch Distillery. Ride a loop through the hills around Lebanon on quiet country roads before enjoying a tasty picnic lunch. After lunch, you’ll get a guided tour of the distillery and a bourbon tasting.

Bike Tour in Kentucky's Bourbon Country

Day 3: Explore Shaker Village and take a guided hayride tour:
Today you’ll explore the many offerings of the Shaker Village area. The morning’s ride will take you northwest, on roads through open farmland in the Salt River watershed. Upon your return to the village, the rest of the afternoon is yours to spend as you like. Choose to ride a bit more, to the small town of Burgin, or set out on a hike through the Preserve which features over 30 miles of trail through native prairies, woodlands, fields, and canebrakes. Or you may opt to take one of the many tours offered daily to learn about the Shakers who lived here around the turn of the nineteenth century. In the late afternoon, you will join your travel companions for a drink and narrated hayride, which will introduce you to the rich history of the village.

Bourbon Trail Bike Trip

Day 4: Ride to Versailles, visit Woodford Reserve, and arrive at the Kentucky Castle:
Ride alongside the Kentucky River and through several of its tributary drainages on the morning ride as you cross unique bridges and pass through forests and small farms. When you arrive in downtown Versailles, you’ll have a number of fresh and delicious lunch options to choose from. Then hop back on your bike for a short ride to Woodford Reserve Distillery, one of Kentucky’s oldest and most highly acclaimed distilleries.

Bourbon Tasting in Kentucky

Day 5: Tour Castle & Key Distillery, enjoy lunch overlooking Glenn’s Creek, and toast your week at the Kentucky Castle
You’ll start your day riding your way to Castle & Key, a small boutique distillery that has recently undergone a careful restoration. The distillery was built in In 1887 by legendary distiller Colonel Edmund Haynes Taylor, Jr. and features a castle, a classical springhouse, and sunken gardens. On a guided walk through the property, you’ll learn about the owners’ from-scratch process of distilling spirits. Enjoy a tasting of their craft then head just down the road to The Stave for lunch. Here, a menu of modern twists on favorite Kentucky dishes awaits while you relax on the patio that overlooks Glenn’s Creek.

Cycling Tour in Kentucky

Day 6: Cycle past the immaculate grounds of the Keeneland Race Track:
Enjoy one final spin through the green pastures of the storied grounds of the Keeneland Race Track, listed on the National Register of Historic Places and once voted the #1 thoroughbred racetrack in North America.

Kentucky Bourbon Trail Bike Tour

Many thanks to our guest, Bob Joy, for contributing the photos for this post!

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