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Kentucky Bourbon Country Bike Tour

Bluegrass, Bourbon, and Horse Country

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. Here in central Kentucky everything feels settled into place and right at home, and we think you will feel the same. 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. Book your trip with confidence »
Explore the Bourbon Trail on a bike tour through Kentucky with Trek Travel
$3899 Per Person
6 Days & 5 Nights
Rider Level: ?
3 / 2 - Active / Recreational Non-riders Welcome
Trip Style: ?
Hotel Level: ?
From $3899 per person View All Details
Trip Wows
Cycle through the horse capital of the world, past the Kentucky Horse Park and countless thoroughbred farms
Learn about equine culture and get up close to the award-winning horses of MeadowCreek Farm on a private tour
Taste the fresh goodness of on-site gardens with farm to table meals at The Trustees' Table and Castle Farms
Indulge in premier spirits during private tours and tastings at the boutique Limestone Branch and Castle & Key Distilleries
Take a guided walking tour of downtown Lexington to learn about the unique history of this special city
Watch the Experience
Kentucky Bourbon Country Bike Tour
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.
-Joan, Trek Travel Guest

Dates & Prices

The Earlier You Book, The Greater The Rewards

We reward our guests with lower pricing and more dates to choose from the earlier you book. Rest assured, once you book, your price and date are guaranteed.
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Single Occupancy from: +$999
May 12 – May 17 
$3899 / Person, Double Occupancy / Plus 6% state and local sales tax Book this date
May 19 – May 24 
Guaranteed Limited Availability
$4199 / Person, Double Occupancy / Plus 6% state and local sales tax Book this date
May 26 – May 31 
$3899 / Person, Double Occupancy / Plus 6% state and local sales tax Book this date
Jun 2 – Jun 7 
$3899 / Person, Double Occupancy / Plus 6% state and local sales tax Book this date
Jun 9 – Jun 14 
$3899 / Person, Double Occupancy / Plus 6% state and local sales tax Book this date
Don't see your ideal travel date? 
Call us at (866) 464-8735 for custom date availability
Looking for a one of a kind, once in a lifetime experience?
Look no further. Choose your trip date, get your group together and we will do the rest. Private trip pricing is as follows:

  • 10+ Guests Price as advertised*
  • 8-9 Guests +$750 per person to trip price*
  • 6-7 Guests +$1,500 per person to trip price*
  • 4-5 Guests +$2,000 per person to trip price*
  • 2-3 Guests +$3,000 per person to trip price*
  • 1 Guest        Call us for pricing*

Traveling with a small group? Consider semi-private trips.
For groups of up to six people, semi-private trips offer unique flexibility within a larger Trek Travel guided trip. Learn more »

*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Private pricing is not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Looking for a date that you don’t see?
Look no further. Simply tell us your preferred travel dates and we’ll work together to deliver the same great trip on your custom schedule.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom dates are not available on Ride Camp, Race, Special Edition or Cross Country style trips.
Want to customize this trip?
We've got you covered. We’ll work with you to build your perfect vacation from scratch, including your choice of riding, accommodations and dining options. With the help of our trip designers and travel experts, the world is available like never before.
*Pricing, availability and guest minimums are all subject to change at any time. Certain dates have a minimum number of guests required, please contact us for details. Custom trips are not available on Ride Camp, Race, Special Edition or Cross Country style trips.

Your Trek Travel guides will meet you at the 21c Museum Hotel Lexington at 10:30 AM on the first day of the trip. After a five-minute private shuttle, you’ll arrive at Smithtown Seafood inside West Sixth Brewery (vegetarian and vegan options are readily available). Here you will be treated to your first of many meals filled with local ingredients and inspired by the local food culture. After this hearty lunch and a short round of introductions, your guides will discuss the rules of bike safety and specific cycling tips for riding in central Kentucky before familiarizing you with your Trek bicycle and ensuring a comfortable fit. Then it's time to take your first pedal strokes through horse country! You'll begin on the Legacy Trail Bike Path and wind your way past the Kentucky Horse Park and into rolling fields of beautiful horse farms. Your ride ends at Evans Orchard Cider Mill before a 30-minute shuttle to the Kentucky Castle. Settle into your room in this unique property, then stroll through the organic garden and visit the resident pygmy goats. This evening we'll gather for a welcome social hour on the castle grounds. Then, toast to the exciting week to come over a flavorful farm to table meal.

Today's Ride:

Legacy Trail to Evans Orchard
Approximately 27 mi | 43 km and 1,315 ft | 401 m


The Kentucky Castle

Included Meals:

Lunch | Social Hour | Dinner

After breakfast this morning, shuttle one hour to MeadowCreek Farm, just outside the town of Lebanon. Here you'll meet the owners of the farm and learn about the world-class standardbred horses bred and trained here. 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, you'll shuttle another 10 minutes to Limestone Branch Distillery, where you can change into your cycling gear. Ride a loop through the hills around Lebanon on quiet country roads before enjoying a tasty picnic lunch. Following lunch, you will be treated to a guided tour of the distillery and a bourbon tasting before shuttling about an hour to your home for the next two nights, the 3,000-acre grounds of the Shaker Village of Pleasant Hill. Check into your simple room in the West Family Dwelling and soak in the history of this unique and peaceful place. For dinner this evening you are free to dine on your own in The Trustees' Table or get your food to-go and enjoy it on the grassy lawn of the village.

Today's Ride:

Limestone Branch Loop
Approximately 26 mi | 41 km and 1,620 ft | 493 m

Today's Activity:

Private Tour of MeadowCreek Farm

Today's Activity:

Tour and Bourbon Tasting at Limestone Branch Distillery


Shaker Village of Pleasant Hill

Included Meals:

Breakfast | Lunch

Today is your opportunity to explore the many offerings of the Shaker Village area. This morning's ride will take you northwest, on roads through open farmland in the Salt River watershed. Upon your return to the village, a gourmet boxed lunch will be waiting for you, and 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: their music, architecture, kitchen practices, farming techniques, and skilled craftsmanship. Conversely, choose to walk through some of the 34 restored structures, check out the extensive garden, or visit some of the animals on the farm. Or you may simply wish to relax in a rocking chair on the lawn and take in a view that hasn't changed since the Shakers' day. 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. Following the hayride, you will enjoy a lovely dinner in The Trustees' Table where the fruits of the Shaker Village's garden and farm as well as those of local farmers will be brought to the table.

Today's Ride:

Salt River Loop
Approximately 33 mi | 53 km and 2,260 ft | 688 m

Avid Option:

Salt River Loop with Burgin Loop
Approximately 49 mi | 78 km and 3,300 ft | 1,005 m

Today's Activity:

Hayride Tour of Shaker Village


Shaker Village of Pleasant Hill

Included Meals:

Breakfast | Lunch | Drink with Hayride | Dinner

After a final breakfast at The Trustees' Table it's time to say goodbye to Shaker Village and point your bike toward the small town of Versailles. Ride alongside the Kentucky River and through several of its tributary drainages on this morning's ride as you cross unique bridges and pass through forests and small farms. When you arrive in downtown Versailles you'll be on your own for lunch, with a number of fresh and delicious options to choose from. Back on your bike, it's more gorgeous miles past thoroughbred farms on your way to your final home on the trip, 21c Museum Hotel Lexington. Take some time to walk around downtown and explore the hotel's impressive contemporary art galleries before venturing into downtown Lexington for dinner on your own.

Today's Ride:

Shakertown to Versailles with Shuttle
Approximately 32 mi | 52 km and 2,600 ft | 792 m

Avid Option:

Shakertown to Lexington
Approximately 56 mi | 90 km and 3,920 ft | 1,195 m

Today's Activity:

Explore Downtown Lexington


21c Museum Hotel

Included Meals:


After breakfast from Lockbox, it's time to head out on your last full day in Bourbon Country. We promise you won't be tired of riding past winding hand-laid stone fences and manicured pastures filled with horses, through tiny towns, and down shaded lanes. After a brief ten minute shuttle to Masterson Station Park, you'll hop on your bike and make your way 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. Next up, head to Castle & Key, a small boutique distillery that has recently undergone a careful restoration. The distillery was built in 1887 by legendary distiller Colonel Edmund Haynes Taylor, Jr. and features a castle, a classical springhouse, and sunken gardens. Take a guided walk through the property and learn about the owners' from-scratch process of distilling spirits. Enjoy a tasting of their craft, then shuttle or ride to Wallace Station before shuttling a half hour back to the hotel. Tonight you'll join your travel companions in the bar at Lockbox for a fun social hour, followed by dinner as you toast your week in horse and bourbon country.

Today's Ride:

Millville Loop
Approximately 47 mi | 76 km and 2,800 ft | 853 m

Short Option:

Masterson Station Park to Millville with Shuttle
Approximately 25 mi | 40 km and 1,390 ft | 424 m

Today's Activity:

Tour and Tasting at Castle & Key Distillery


21c Museum Hotel

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

On the final morning of your trip you'll lace up your walking shoes for a fun, interesting and highly informative walk around downtown Lexington with a knowledgeable local tour guide. Learn about the history, artists and unique characters of this fascinating city as you walk the streets, visit notable landmarks, and visit a locally-owned art gallery. It's a relaxing way to wrap up your time in the Bluegrass State. Upon your return to the hotel, you'll have time to freshen up before check-out. A private Trek Travel shuttle will depart from the hotel at 11:00 AM. You’ll then say farewell to your guides at 11:15 AM at the Blue Grass Airport. Please do not schedule a flight out before 1:00 PM on the last day of the trip to allow plenty of time for any unforeseen delays.

Included Meals:



hotel image

The Kentucky Castle

Versailles, Kentucky

Luxury Accommodation | Is that a castle in the middle of horse country? You bet it is. The main entrance to this enchanting hotel opens to a lobby with a grand staircase where you will be welcomed and shown to your room in the castle. A farm to table restaurant called Castle Farms, pool and spa, organic garden, koi pond, and fire pit complete this experience fit for a king and queen. There's literally no other property in Kentucky like it.
hotel image

Shaker Village of Pleasant Hill

Harrodsburg, Kentucky

Explorer Accommodation | Join us as we step back in time to a simpler era at Shaker Village. Sitting on 3,000 acres of untouched farmland, prairie, and forest, this property is exceptional at delivering the simpler, finer things. Stroll the gardens and enjoy miles of trails before dinner at the property's farm-to-table restaurant, and then relax in your simple but spacious room, located in the country's largest private collection of original 19th century buildings. Trek Travel guests will also enjoy a private hayride tour and some relaxed, unstructured free time to unwind from the rigors of everyday life. Please note that the accommodations at Shaker Village are quite basic and can feel rustic, as they reflect the simple lifestyle of the original Shakers.
hotel image

21c Museum Hotel Lexington

Lexington, Kentucky

Explorer Accommodation | At first, you may think this unique hotel conspires to confuse you. Is it an art gallery? Is it a boutique property? The answer is 'yes.' The name is a testament to its commitment to the art of today, showcasing living, working 21st century artists. The entranceway, lobby, restaurant, upstairs gallery spaces, and even elevator landings feature this art, and much of the building is a work of art itself. 21c's design seamlessly blends the architecture of its history with modern touches, while an extremely walkable location will assure that you're in the center of the action during your stay.

What's Included

For us, the details matter most

Every moment of a Trek Travel bike trip has more than you could have ever dreamed. More romance. More scenery. More choice. It's the little additions to every Trek Travel cycling vacation that make it truly special. And that's how we help you create more memories.


Trek Domane SL 7

Experiencing your cycling vacation of a lifetime is not complete without a world-class bike and the Trek Domane is the best way to enjoy the ride. Trek Bikes has launched the all-new Trek Domane and now you can ride it on our trips. It raises the bar to deliver incredible endurance road bike comfort without sacrificing performance and features highly responsive disc brakes and electronic shifting. This new bike is lighter than ever before, and carbon wheels come standard on every bike. The road-smoothing IsoSpeed technology lets you ride as long as you want with less fatigue. The bike you ride on a biking vacation matters. That is why we provide the newest and best bikes in the business. Learn More


Trek Electric-Assist Verve+

With its Low-Step frame design, hopping on and off the Trek Verve+ is super easy. The front suspension will take the edge off any bumps in the road and the Bosch system will keep you smiling from ear to ear. The integrated battery keeps this bike looking sleek as you pedal through amazing terrain. Learn More


  • Five nights of accommodation at handpicked hotels
  • Two experienced guides to provide local knowledge, support, and camaraderie
  • Daily route support with both guides and our support van
  • Daily breakfast, four lunches, and three dinners
  • Two social hours of drinks and hors d'oeuvres and a drink provided before the hayride at Shaker Village
  • Ride a Trek Domane SL 7 disc or Trek Electric-Assist Verve+
  • Daily route options
  • Snacks and drinks for each day's ride
  • Trek Travel Santini cycling jersey to keep
  • Trek Travel water bottles to keep
  • Cinch sack day bag to keep
  • Each bike is equipped with a Garmin Edge 1030 GPS computer, a flat pack (containing a tube, levers, and a CO2 cartridge with inflator), front and rear Bontrager Flare R lights, a Bontrager saddle, and pedals (Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals)
  • Bontrager WaveCel helmets
  • All gratuities for drivers, local experts, and hospitality staff
  • All luggage transfers and transportation during your trip
  • A digital photo album of your trip
  • Entrance fees for all activities, private tours, and events


  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek Electric-Assist Verve+
  • Trek Travel Santini cycling jersey to keep
  • Trek Travel water bottles to keep
  • Shimano clipless road pedals, Shimano clipless mountain pedals, caged, or flat pedals
  • Bontrager WaveCel helmet
  • Bontrager men's and women's specific saddles
  • Bontrager front and rear Flare R lights
  • A flat pack containing a tube, levers, and a CO2 cartridge with inflator
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Coupon valued up to $500 off a new Trek Bicycle. Your coupon will be delivered via email.
  • For the most comfortable ride, you may choose to bring your own pedals, saddle, and helmet on the trip. Your guides will install your gear on the first day during your bike fit.


Guide gratuities are customary and at your own discretion, to recognize service, hospitality, and the little extras that surprise and delight. For this trip, we suggest a tip for your guides between $240-$300 per guest and, of course, you may choose to give more if your guides made your trip an unforgettable experience. While local currency is preferred, there are other options to make tipping easier. Most guides accept gratuity via PayPal or Venmo or our staff can help before or after the trip. Gratuities will be divided among the guide team, so feel free to leave your gratuity with whomever you choose at the end of your trip.
  • Airfare and transportation to and from the trip pick-up/drop-off locations
  • Lodging before and after the trip
  • Personal items purchased during the trip
  • Optional activities not scheduled by Trek Travel
  • On select trips some meals are not included. On these trips, Trek Travel invites you to explore the local cuisine at your leisure.

More Information

Rider Level: 3 - Active?

55 kilometers / 33 miles
265 kilometers / 165 miles
645 meters / 2,119 feet
3,229 meters / 10,595 feet
The terrain is varied throughout the week but generally features smooth, mostly quiet roads through rolling to hilly countryside. The riding on some days of the trip is undulating, while other days feature more hills and climbing. Some of the climbs are short but quite steep. The routes have been designed to avoid busy roadways as much as possible, however, short sections of busy roads are unavoidable. Your guides will make you aware of such sections so you may shuttle if you so choose. Please be aware that the backroads in this region are quite narrow (many do not feature a centerline) and there are almost no shoulders. Kentucky is best suited for our Type 2/3 Riders. Our Trek Travel guides can accommodate Type 2 Riders, who seek less mileage or fewer uphills, with a boost in the van. Those who wish to ride every mile but are concerned about their physical ability may want to try our electric bike option–you still get a workout but can climb alongside even the strongest rider. Type 3 Riders will enjoy the extra mileage and climbing the avid route options offer.
On most Trek Travel trips, we offer non-riding options for riders who want to take the afternoon off, or travel companions who want to spend little or no time in the saddle. Some of these options may need to be scheduled before your trip–please contact one of our Trip Consultants for more information. Expenses and/or related transportation to these activities may not be included in the trip price. Some non-riding options on this trip are:
  • Private tour of MeadowCreek Horse Farm
  • Private tour and bourbon tasting at Limestone Branch Distillery
  • Hayride Tour at Shaker Village of Pleasant Hill
  • Participate in some of the many tours available daily at Shaker Village
  • Hike on the 36 miles of trails on the Preserve at Shaker Village
  • Enjoy a cocktail at Woodford Reserve Distillery
  • Private tour and tasting at Castle & Key Distillery
  • Enjoy a spa treatment at The Kentucky Castle Spa (not included in trip price)

See Itinerary for specific daily ride distances and elevation options. On all of our vacations, Trek Travel seeks to find quiet, paved secondary roads or bike paths to experience a region; busy roads are avoided as much as possible. Our itineraries are an approximation of our trips. Trek Travel strives to offer every guest a vacation of a lifetime on every trip. At times routes, hotels, activities, etc. listed here may change at the discretion of the trip designer or guides to improve the trip experience.

Averages and totals are calculated from our "Today’s Ride" options.

Travel Details

How to Get There

Blue Grass Airport (LEX)
10:30 AM
21c Museum Hotel Lexington

Say Farewell

Blue Grass Airport (LEX)
11:15 AM
Blue Grass Airport


We suggest that you arrive at least one day prior to the trip start, which will enable you to adjust to the time zone and minimize the risk of missing the trip start due to flight-related delays. We recommend that you fly into the Blue Grass Airport (LEX).

From the Blue Grass Airport you can call or hail a taxi to take you downtown. It is approximately seven miles from the airport to the meeting day hotel in downtown Lexington and a taxi ride should take about 15-20 minutes and cost $30-$35.

Your Trek Travel guides will meet you at the 21c Museum Hotel Lexington at 10:30 AM on the first day of the trip. You’ll then shuttle five minutes to Smithtown Seafood inside West Sixth Brewery. Please have your first day's cycling clothes easily accessible, separate from your luggage, or you may choose to wear your cycling clothes (your luggage will be transported directly from 21c Museum Hotel to the Kentucky Castle, the first night's hotel). You'll enjoy a fresh, delicious lunch and your guides will ensure you are fit comfortably on your bike for the week. After a brief orientation and safety talk, you'll then saddle up to begin the day's ride.

If you will be late for the pick-up or are going to miss it altogether, please inform your guides. You will receive an email a week before the trip starts with their names and contact details. If you cannot reach them, please call our first hotel, the Kentucky Castle (859-256-0322), and leave a message with your expected arrival time and contact details.

View our pre hotel recommendations


You will say farewell to your guides at 11:15 AM at the Blue Grass Airport. Please do not schedule your flight any earlier than 1:00 PM.

View our post hotel recommendations

Planning For Your Trip

Packing and Weather

During the month of May, expect daytime temperatures in the mid-70s and nighttime lows in the mid-50s. In early June, the average high is in the low 80s and the average low is around 60 degrees. Please check the forecast in the days prior to your departure, always be prepared to dress in layers, and bring your rain gear, as rain is always a distinct possibility in this region. Remember to bring along a swimsuit if you wish to enjoy the pool at the Kentucky Castle; comfortable closed-toe shoes for the MeadowCreek Farm tour on Day 2; long pants for the Day 3 wagon ride at Shaker Village and walking shoes for the Day 6 walking tour of downtown Lexington. Packing List

Before and After Your Trip


Before & After: Lexington, Kentucky

Lexington has a vibrancy that's simultaneously unique and age-old. Considered the "Horse Capital of the World" and home to some of the country's most famous bluegrass music, Kentucky's second largest city has a new vibrance since its most recent revitalization in recent years. Enjoy its craft beer, art and music, and incredible food culture while you take a stroll through the University of Kentucky. Don't miss a stop at National Provisions, the city's newest food hall, and grab a mint julep at Bluegrass Brasserie. Or simply walk down National Avenue and enjoy its cute shops, coffeehouses, and pure Kentucky soul. We recommend the following accommodations for your pre- and post-trip hotel.

Why Trek Travel

Our Bikes

Our unrivaled selection of Trek Bikes sets the bar for quality and comfort. From the ultra-smooth Trek Domane SL 7 to the Trek Electric-Assist Verve+, you deserve the best ride on your vacation. Plus, we offer a range upgrade options to take you the extra mile.

Our Guides

Our guides are trained to make your trip magical. They aren't just experts in riding; they're trained in delivering uncompromising service in ways you won't believe. We know that it's the unexpected surprises that make a trip magical. That's why our guides pride themselves on anticipating your needs before you ask.

Your Day. You Decide.

Our vacations are built to deliver the ultimate in flexibility, from extreme relaxers to hard-core roadies. You pick your mileage, itinerary and experiences. We take care of the rest.

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