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Kentucky Bourbon Country

Bluegrass, Bourbon and Horse Country

The rolling hills of Kentucky bluegrass draw your eyes to the horizon, meandering stone fences and bluegrass music take your mind back in time, and endless miles of shaded country roads draw your heart around the next bend. Here in the Bluegrass Region of central Kentucky, everything feels settled into place and right at home, and we think you will too. 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 the bustle of downtown Lexington to quiet, starlit lights at a well-preserved historic Shaker village, on to your own room in a castle near Versailles. Soak in the history, the stories and the craftsmanship around every corner that make the Bluegrass State such a special place to visit.
From:
$3099 Per Person
Duration:
6 Days & 5 Nights
Rider Type: ?
3 / 2 - Active / Recreational Non-riders Welcome
Hotel Style: ?
Explorer
From $3099 per person View All Details
Trip Wows
Cycle through the horse capital of the world, past the Kentucky Horse Park and Keeneland Race Track
Endulge in premier spirits during a private tour and tasting at the boutique Castle & Key Distillery
Lose yourself in a bygone era as you learn about the history of the Pleasant Hill Shakers on a guided hayride tour and take a cruise on the Kentucky River aboard the Dixie Belle Riverboat
Taste the fresh goodness of on-site gardens with farm to table meals at the Trustee's Table and Castle Farm
Learn about equine culture and get up close to the award-winning horses of MeadowCreek Farm on a private tour
Watch the Experience
Our trip through the Bluegrass Region of Kentucky is designed to celebrate all the things this beautiful area is rightfully known for: horses, bourbon whiskey, warm hospitality and the quiet beauty of rural America. With amazing roads and a rich history to be discovered, this area is a fantastic cycling destination. We look forward to sharing the culture and the flavors of Bourbon Country with you.
-Rebecca Falls, Trip Design Coordinator

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.
Guaranteed
to run
?
Sold Out/
Waitlist
?
Private/
Reserved
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Limited
Availability
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Single Occupancy from: +$800
?
Group
Discounts
?
May 3 – May 8 
Guaranteed
$3099 / Person, Double Occupancy Book this date
May 10 – May 15 
Guaranteed
$3099 / Person, Double Occupancy Book this date
May 17 – May 22 
Guaranteed
$3099 / Person, Double Occupancy Book this date
May 31 – Jun 5 
Guaranteed
$3099 / Person, Double Occupancy 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. All you need to do is pick any open 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 +$500 per person to trip price*
  • 6-7 Guests +$1,000 per person to trip price*
  • 4-5 Guests +$1,500 per person to trip price*
  • 2-3 Guests +$2,500 per person to trip price*
*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 20-minute private shuttle, you’ll arrive at the Windy Corner Market. Here you will be treated to your first of many meals filled with local ingredients and inspired by the local food culture. The Market is fashioned after an old country store and we think you'll feel right at home walking up to its well-worn counter. 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 wind your way near Georgetown, past the Kentucky Horse Park and onto the Legacy Trail Bike Path. This path will take you into the outskirts of downtown Lexington, where you will then make your way past West Sixth Brewing, through the Brucetown neighborhood and on to your hotel for the night, the 21c Museum Hotel Lexington. Take some time to walk around downtown and explore the hotel's impressive contemporary art galleries before joining the group in the bar at Lockbox for a fun social hour, followed by dinner. (Please note that in the event of inclement weather you will have brunch at Zim's Cafe in downtown Lexington immediately after meeting the group at 10:30 AM. You will then shuttle to Windy Corner Market for the bike fitting and to begin the day's ride. As the sister property of Windy Corner Market, Zim's has the same menu so only the location of this meal will change in the event of rain.)

Today's Ride:

Windy Corner to Lexington
Approximately 34 miles with 1,590 feet of climbing

Today's Activity:

Explore Downtown Lexington

Hotel:

21c Museum Hotel Lexington

Included Meals:

Lunch | Social Hour | Dinner

After an early breakfast this morning you will shuttle an hour and fifteen minutes to MeadowCreek Farm, just outside of the town of Lebanon. Here you will meet the owners of the farm and learn about the world-class standardbred horses they breed and train here. The farm is home to several impeccably pedigreed horses with impressive wins on their resumes! After the tour, you'll change into your cycling clothes and begin today's ride. Lebanon is also home to the Kentucky Cooperage, which manufactures most of the oak barrels used for aging by the bourbon industry, and we'll ride right past on our way out of town. Quiet country roads abound on this morning's ride to the Perryville Battlefield State Historic Site, where you will break for a picnic lunch prepared by your Trek Travel guides. This site marks the location of Kentucky's most destructive Civil War battle, fought in 1862. If you've had enough riding for the day you can shuttle from lunch to the hotel, or you may continue riding past Harrodsburg, Kentucky's oldest city, and onto the 3,000-acre grounds of the Shaker Village of Pleasant Hill. Here you will check into your simple room in the East Family Dwelling before gathering for a welcome drink and narrated hayride, which will introduce you to the rich history of this unique and peaceful place. Following the hayride, you will enjoy a lovely dinner in the Trustee's Table where the fruits of the Village's garden and farm as well as those of local farmers will be brought to the table.

Today's Ride:

Lebanon to Perryville Battlefield State Park with Shuttle
Approximately 23 miles with 1,170 feet of climbing

Avid Option:

Lebanon to Shakertown
Approximately 53 miles with 2,940 feet of climbing

Today's Activity:

Tour MeadowCreek Farm

Hotel:

Shaker Village of Pleasant Hill

Included Meals:

Breakfast | Lunch | Dinner

Today is your opportunity to explore the many offerings of the Shaker Village area. This morning's ride options will take you to the northwest of the village, 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. 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- 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 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 on the Dixie Belle Riverboat for a 1-hour cruise on the Kentucky River, along the exposed limestone cliffs and outcrops known as the Palisades. For dinner this evening you are free to dine at your leisure in the Trustee's Table (this meal is included in the price of your trip but will not be a group dinner).

Today's Ride:

Salt River Loop
Approximately 33 miles with 2,260 feet of climbing

Avid Option:

Salt River Loop with Salvisa Loop
Approximately 51 miles with 3,450 feet of climbing

Today's Activity:

Cruise the Kentucky River Palisades by Riverboat

Hotel:

Hotel Name

Included Meals:

Breakfast | Lunch | Dinner

After a final breakfast at the Trustee's 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 a short ride to Woodford Reserve Distillery, one of Kentucky's oldest and most highly acclaimed distilleries. Take a moment to wander the grounds and the gift shop or participate in a tasting if you like. You'll hop back on your bike to pass through thoroughbred farms on your way to your final home on the trip, The Kentucky Castle. Settle into your room in this unique property and stroll through the organic garden and visit the pygmy goats. This evening your guides will shuttle you to the nearby town of Midway for a dinner of your choice.

Today's Ride:

Shakertown to Woodford Reserve with Shuttle
Approximately 42 miles with 3,150 feet of climbing

Short Option:

Nonesuch to Woodford Reserve with Shuttle
Approximately 31 miles with 2,360 feet of climbing

Avid Option:

Shakertown to Woodford Reserve to Westmoreland
Approximately 61 miles with 4,400 feet of climbing

Hotel:

The Kentucky Castle

Included Meals:

Breakfast

After a farm-fresh breakfast from Castle Farms 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. You'll make 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. Here you will learn about the new owners' passionate dedication to locally-sourced ingredients and their 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. A pleasant ride takes you back to the Castle where you can enjoy the pool that lies inside the castle walls or take advantage of the Castle Spa next door (reservations are recommended and spa treatments are not included in the price of your trip). This evening you will gather for a final celebratory social hour on the castle grounds. Toast your week in horse and bourbon country over another farm to table meal.

Today's Ride:

Millville Loop
Approximately 46 miles with 2,860 feet of climbing

Short Option:

Westmoreland to Millville with Shuttle
Approximately 23 miles with 1,260 feet of climbing

Today's Activity:

Tour and Tasting at Castle & Key Distillery

Hotel:

The Kentucky Castle

Included Meals:

Breakfast | Lunch | Social Hour | Dinner

Enjoy one final spin through the green pastures that will surely feel like home by now. Ride through 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. Upon your return to the Castle, you'll have time to freshen up before check-out. If you’d rather skip the ride, you are welcome to sleep in and enjoy a leisurely breakfast. 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. If necessary, your guides can provide transportation back to the 21c Museum Hotel Lexington and should arrive around 11:45 AM. 

Today's Ride:

Keeneland Loop
Approximately 23 miles with 1,640 feet of climbing

Included Meals:

Breakfast

Hotels

hotel image

21c Museum Hotel Lexington

Lexington, Kentucky

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 the best 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 at every moment.
hotel image

Shaker Village of Pleasant Hill

Harrodsburg, Kentucky

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 welcome tour, a riverboat cruise, and some relaxed, unstructured free time to unwind from the rigors of everyday life.
hotel image

The Kentucky Castle

Versailles, Kentucky

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. Maybe even in the world.

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.

bike

Trek Domane SL 7 Disc

It isn’t the cycling vacation of a lifetime unless you have the industry’s best bike to match. In 2019 we upgraded our fleet to feature the award-winning Domane SL 7 with Shimano Ultegra Disc brakes. Because when you combine the lightweight stability and comfort of the Domane with the superior safety and stopping power of disc brakes, you get a match made in cycling heaven. And the best part? It’s included in the trip price. Ride confidently, comfortably and longer in the most beautiful destinations around the world with the new Domane SL 7. Learn More

bike

Trek Electric-Assist XM700+

It’s lightweight and equipped with an adjustable pedal-assist motor that helps riders of all skill levels stay together, play together and make some great memories together. Included at no additional cost, these bikes will be available on a first-come, first-served basis, so reserve yours when you book today. Learn More

WHAT'S INCLUDED

  • 5 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, 4 lunches and 4 dinners
  • 2 social hours of drinks and hors d'oeuvres
  • Ride a Trek Domane SL 7 disc or Trek's newest Electric-Assist
  • Daily route options
  • Snacks and drinks for each day's ride
  • Trek Travel Bontrager 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, flat pack, 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 personalized photobook of your trip
  • Entrance fees for all activities, private tours and events

GEAR

  • Trek Domane SL 7 disc carbon road bike with Shimano Di2 electronic shifting or Trek's newest Electric-Assist
  • Trek Travel Bontrager 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 and a flat pack
  • Garmin Edge 1030 GPS computer
  • Cinch sack day bag to keep
  • Upgrade your bike to include carbon wheels (+$200)
  • 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.

WHAT'S NOT INCLUDED

Gratuities for your Trek Travel guides are not included in your trip price. We recommend tipping 7.5-10% of your trip price for the guide team. Local currency is preferred and unless you want to tip separately, guides will divide tips amongst themselves. Please tip your guides at your discretion, based on their level of professionalism, guest care and service.
  • 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?

AVERAGE DAILY MILEAGE:
34 miles
TOTAL MILES:
201 miles
AVERAGE DAILY ELEVATION:
2,112 feet
TOTAL ELEVATION:
12,670 feet
TERRAIN: UNDULATING
The terrain is varied throughout the week but generally features smooth, mostly quiet roads through rolling countryside. The riding on some days of the trip is gently undulating, while other days feature more hills and climbing. 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 also 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.
NON-RIDING ACTIVITIES:
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
  • Hayride Welcome Tour of 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
  • Dixie Belle Riverboat Cruise
  • Bourbon Tasting 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 strives 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

FLY INTO:
Blue Grass Airport (LEX)
MEETING TIME:
10:30 AM
MEETING LOCATION:
21c Museum Hotel Lexington

Say Farewell

FLY OUT OF:
Blue Grass Airport (LEX)
DEPARTING TIME:
11:15 AM
DEPARTING LOCATION:
Blue Grass Airport

Arriving

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 7 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. Alternatively, our meeting day hotel, 21c Museum Hotel Lexington, offers an airport shuttle. The shuttle is $20 per person and must be arranged by calling the hotel front desk prior to your stay.

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 20 minutes to Windy Corner Market. Please have your first day's cycling clothes easily accessible, separate from your luggage, or you may choose to wear your cycling clothes (the 21c Museum Hotel will store your luggage for the day and deliver it to your room when possible, so you will not have your luggage with you during the day today). You'll enjoy a fresh, delicious lunch prepared by the market 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. (Please note that, in the event of inclement weather you will have brunch at Zim's Cafe in downtown Lexington immediately after meeting the group at 10:30 AM. You will then shuttle to Windy Corner Market for the bike fitting and to begin the day's ride. As the sister property of Windy Corner Market, Zim's has the same menu so only the location of this meal will change in the event of rain.)

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, 21c Museum Hotel Lexington (859-899-6800), and leave a message with your expected arrival time and contact details.

View our pre hotel recommendations

Leaving

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 12:45 PM. If you need transportation back to downtown Lexington your guides can return you to the 21c Museum Hotel Lexington following the airport dropoff, arriving around 11:45 AM.

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 possibility in this region. Remember to bring along shoes you will be comfortable in for the MeadowCreek Farm tour; long pants for the Day 2 hayride; a hat for the riverboat cruise and a swimsuit if you wish to enjoy the pool at the Kentucky Castle. Packing List

Before and After Your Trip

before

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 2nd 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 all-new, ultra smooth Trek Domane SL 7, to the new Trek Electric-Assist XM700+ and the comfortable Trek 7.6 FX Hybrid, to our numerous upgrade options, you deserve the best ride on your vacation.

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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