Kentucky Bluegrass & Bourbon Bike Tour

Kentucky Bluegrass & Bourbon Bike Tour


Lexington, Kentucky is known as the “Horse Capital of the World” and the center of Bluegrass country. Kentucky itself is packed with history, culture and art. This ideally located small city sits within a day’s drive for two thirds of the US population and should not be missed.

Kentucky is probably best known for its Bluegrass Region. Located in north central Kentucky, the core of the Bluegrass is gently rolling pastures and characterized by sinkholes, streams and springs. The region’s limestone-purified water is recognized as the key factor for the making of Kentucky Bourbon. The weathering limestone has produced the state’s most fertile soil, and make the horse farms that sprawl across the rich pastures a Kentucky icon.

The Kentucky Horse Park is Lexington’s premier attraction and home to 50 horse breeds, museums and exhibits of the horse and racing industry. Keeneland Race Course is steeped in history and known for its beauty, and was the first track in the country to incorporate an artificial running surface. Keeneland is the crown jewel of horse racing tracks and is the world’s leading thoroughbred auction house. While on our cycling tour, we take an early morning to have breakfast in the jockey’s cafeteria, tour the facilities and then take the afternoon to tour the Horse Park and Museum.

The countryside surrounding Lexington is covered with black wooden and stacked stone fences guarding beautiful farms and their prized thoroughbreds. The pastures are emerald Bluegrass with beautiful thoroughbreds running off their winter blues. Well-manicured estates and barns are as beautiful as most homes cover the rolling hillsides.

The downtown area of Lexington has seen a resurrection in the last ten years. It now is a hot bed for fine old inns, upscale dining, shopping and walking paths.

The eastern and southern outskirts of Lexington are home to towns like Berea and Harrodsburg, where fine art is alive and thriving. The small town of Berea is home to artists that include everything from pottery to painting to furniture makers. Many of these artisan are the product of Berea College.

Harrodsburg, founded in 1774, was the first permanent English settlement west of the Appalachians. You will discover places of the pioneer past and America’s largest restored Shaker Village. In Fort Boonesborough, enjoy live actors as they educate and entertain you with live re-enactments of the times and tribulations of this pioneer village built by Daniel Boone.

Besides the horse industry, Kentucky Bourbon plays an important part in the history and economy of Kentucky. There are more than 20 Bourbon distilleries in Kentucky, several right in and around Lexington. Some still operate in “dry” counties. Most distilleries offer tours and they are worth visiting because each has their own mash receipes, yeast strands, charred aged barrels and aging processes. It makes a wonderful, entertaining day should we meet up with a cold, rainy day of cycling.

Kentucky is not a state that you think of for cycling. But, it has gentle terrain, beautiful scenery and it is easy to get to.



Rider Level

Recreational – Active


332 miles; 16,663 feet of elevation


If you are driving to this tour, our meeting place will be Holiday Inn in Versailles, KY. If flying in, schedule your flights in and out of Lexington’s Blue Grass Airport. We will pick you, your bike and luggage up at the baggage carrousel at 4pm.


All meals are included


All lodging is included

  • All lodging
  • Transfers to and from the airport
  • All breakfasts, dinners and picnic lunches on riding days
  • Cocktail social hours on the 1st evening of each tour
  • Van support
  • Maps
  • GPS mapping
  • Mechanic
  • 2 or more experienced guides
Not Included
  • Airfare
  • Meals on off days
  • Souvenirs
  • 12% gratuity for guides, mechanics, volunteers and tour staff is not included, but greatly appreciated


  • October 10 – 16, 2022
  • May 13 – 19, 2023
  • Sunday – Saturday
  • 6 Days | 6 Nights


Per Person
  • Single Room - $750
    Road Bike - $175
    e-Bike: $375
Bourbon and bluegrass, so much fun ... book this tour today!


Day 1

North Lexington to Paris to North Lexington

53.7 miles; 2757 ft elevation

Day 2

North Lexington to Versailles; KY Horse Park and Keeneland Racetrack. Unique Horse Farm Tour.

35.7 miles; 1572 ft elevation

Day 3

Versailles to Midway to Versailles; Midway Café and Woodford Reserve Distillery.

45.6 miles; 2087 ft elevation

Day 4

Versailles to Shaker Village; Cross the KY River.

42.5 miles; 3102 ft elevation

Day 5

Shaker Village to Berea; Boone Tavern Lancaster.

56 miles; 3511 ft elevation

Day 6

Berea to North Lexington; Talon Winery, Transylvania Univ.

49.2 miles; 2639 ft elevation

“Super beautiful, well done! If you are looking for a magical and romantic place then this is a great place to go! I’d recommend this to anyone who loves a good adventure!”
Ali McBeth

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