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Kentucky Bourbon Country Bike Tour

Bluegrass, Bourbon, and Horse Country in Versailles, Shakertown, and Lexington

Tour Duration

6D / 5N

Trip Style

Signature, Classic Guided

Activity Level

2, 3

Hotel Level



Trek Domane SL 7
Trek Electric-Assist Verve+
Trek Electric-Assist Domane+ SLR 7

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Starting from

$3,799.00 per person

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Experience the beauty of the Bluegrass State as you explore verdant landscapes, world-class horse farms, and the vibrant heart of Lexington.

The rolling hills of Kentucky bluegrass draw your eyes to the horizon, meandering stone fences and old-time music take your mind back in time and endless miles of shaded country roads draw your heart around the next bend. Ride past world-class horse farms, taste fine bourbon straight from the source, and trace the paths of the Kentucky and Salt Rivers through lush green landscapes as you discover the many faces of this beautiful region. You will flow from your own room in a castle near Versailles to starlit lights at a well-preserved historic Shaker village and on to lively downtown Lexington. Soak in the history, the stories, and the craftsmanship around every corner that make the Bluegrass State such a special place to visit.

Trip Wows
  • Cycle through the horse capital of the world, past the Kentucky Horse Park and countless farms

  • Indulge in premier spirits during private tours and tastings at the boutique Limestone Branch and Castle & Key Distilleries

  • Immerse yourself in a bygone era as you learn about the history of the Pleasant Hill Shakers

  • Learn about equine culture and get up close to the award-winning horses of MeadowCreek Farm on a private tour

  • Enjoy a guided walking tour of downtown Lexington and learn about the interesting history of this unique city

Two horses sniff noses

MeadowCreek Farm

Private horse farm tour

Get a glimpse behind the scenes at the beautiful MeadowCreek Farm.

What Guests are Saying
Woman in cycling gear with a horse

Kentucky is an amazing place to ride. The road surfaces were some of the best we have experienced. The beauty of the surrounding farms was a joy to see each day. We also loved the visit to Jimmie’s horse farm and the different distilleries. This was one of our favorite trips due to the itinerary and beautiful countryside.

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Joan, Trek Travel Guest

A group of cyclists pose in front of a wall mural

My wife and I just finished a week of riding through Bourbon Country. If you like scenic country roads with smooth pavement, short but challenging hills, and patient drivers, this is the trip for you! It was a fantastic trip and I don't even like bourbon.

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Bob, Vero Beach, FL

Couple standing with their bikes in a forested area

We would repeat this trip next week! Beautiful surroundings, fun sights, nice hotels, terrific guides, and great riding.

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Teresa, Lexington, KY

Group at a gourmet picnic

There was very little traffic and the routes were outstanding. There was no shortage of food and drink before, during and after the rides. The guides were exceptional. There was a good balance of riding and non-riding activities. It was the best biking week of my life!

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Steve, Green Bay, WI

Three cyclists ride across iron bridge

Great Ride

Wilmore to Versailles

Ride alongside the Kentucky River and several of its tributary drainages as you cross unique bridges and pass through forests and small farms.

Dates & Pricing

Book early for the best price

  • Guaranteed

  • Join Waitlist

  • Private

  • Limited Availability