- 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*
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.)
Windy Corner to Lexington
Approximately 34 miles with 1,590 feet of climbing
Explore Downtown Lexington
21c Museum Hotel Lexington
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.
Lebanon to Perryville Battlefield State Park with Shuttle
Approximately 23 miles with 1,170 feet of climbing
Lebanon to Shakertown
Approximately 53 miles with 2,940 feet of climbing
Tour MeadowCreek Farm
Shaker Village of Pleasant Hill
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).
Salt River Loop
Approximately 33 miles with 2,260 feet of climbing
Salt River Loop with Salvisa Loop
Approximately 51 miles with 3,450 feet of climbing
Cruise the Kentucky River Palisades by Riverboat
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.
Shakertown to Woodford Reserve with Shuttle
Approximately 42 miles with 3,150 feet of climbing
Nonesuch to Woodford Reserve with Shuttle
Approximately 31 miles with 2,360 feet of climbing
Shakertown to Woodford Reserve to Westmoreland
Approximately 61 miles with 4,400 feet of climbing
The Kentucky Castle
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.
Approximately 46 miles with 2,860 feet of climbing
Westmoreland to Millville with Shuttle
Approximately 23 miles with 1,260 feet of climbing
Tour and Tasting at Castle & Key Distillery
The Kentucky Castle
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.
Approximately 23 miles with 1,640 feet of climbing
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.
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
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
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.
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
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
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
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.
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 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.
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.