Kentucky Bike Tour
Kentucky Bike Tour
Kentucky Bike Tour
Kentucky Bike Tour
Kentucky Bike Tour
Kentucky Bike Tour
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Kentucky Bike Tour

Legendary Bourbon Trail™ — Louisville to Lexington

Couples, Friends & Solos

5 days 4 nights

Activity Level: 2-4

Premiere Hotels

From: $3,499 - $3,749 pp dbl occ

($750 - $800 for sgl occ)

Kentucky breeds passion. Its bluegrass landscape nurtures prized Thoroughbreds and inspires musicians. Bourbon spirits are carefully crafted and revered here. Horse racing legacy turns up around every corner. Historic monuments and enchanting estates tell tales of the past. Southern hospitality nourishes its warm and welcoming culture. Before you know it, you might find yourself attached to all of Kentucky's obsessions.

Kentucky Biking
Kentucky Biking


Start Louisville / End Lexington or Louisville

Start/End locations may vary. Do not book flights until your trip details are confirmed.


  • Bike the Kentucky Bourbon Trail® and ride through stunning farmland with grazing horses and green as far as the eye can see
  • Learn about the fine art of distilling and sample for yourself the craft and big-label bourbons that make Kentucky famous
  • Pedal past renowned Thoroughbred farms, perhaps catching sight of famous (or hoping to be famous!) stallions bred to race in the Derby
  • Explore the roots of the Bluegrass State—from a historic Shaker community to traditional bluegrass music
The Backroads Experience
The Backroads Experience
Biking Tours
Biking Tours
Backroads Trip Leader
Meet Our Leaders


Accommodations may vary based on departure date.
5 Days Premiere Hotels*
Accommodations may vary based on departure.
Day 1

From Louisville, venture to true bluegrass country, where our journey begins | Bike through rolling farmland, wooded areas and peaceful country roads | History unfolds in Harrodsburg with buildings dating back to the 1850s | Stay in Shaker Village, once the third largest Shaker community in the United States | Join a private tour of the farm before a down-home dinner of Kentucky dishes made with ingredients from Shaker Village's garden.

Shaker Village of Pleasant Hill, Harrodsburg, Kentucky
Shaker Village Inn
| *Casual Hotel

Located within the 3,000 acres of National Historic Landmark Shaker Village, the hotel is built in restored Shaker buildings and offers simple rooms furnished with Shaker reproduction furniture and lovely countryside views.

Days 2-3

Ride an undulating route passing rushing rivers and verdant hillsides dotted with barns and lined with stacked stone walls | Journey to Frankfort, the state’s charming riverside capital city boasting a downtown rich in culture and historical architecture | Make yourself at home at Kentucky Castle, a striking medieval-inspired hotel complete with stone walls and turrets plus its own working farm | Follow postcard-perfect country lanes past expansive estates, grazing horses and boutique distilleries.

The Kentucky Castle, Versailles, Kentucky
Kentucky Castle
| Premiere Hotel

Named the "Most Beautiful Hotel in Kentucky" by Architecture Digest, this medieval-style castle hotel dishes out the royal treatment with its farm-to-table restaurant, attention to hospitality, sprawling grounds and an amazing rooftop where you can watch the sun set. (pool, spa)

Days 4-5

Bike through pastureland dotted with stables and Thoroughbreds near Lexington, often called the Horse Capital of the World | Enjoy a bluegrass performance while savoring Southern cuisine | Get an incredible behind-the-scenes look at one of the world's premier Thoroughbred race farms and see a few celebrity horses, including winners of the Kentucky Derby | Take time to wander around the exhibitions at our boutique hotel’s contemporary art museum | Savor one last ride along a favorite route of locals, followed by a visit to a historic distillery. 

21c Museum Hotel, Louisville, Kentucky
21C Museum Hotel
| Premiere Hotel

Set in a historic downtown building, this boutique hotel embraces the modern with its 7,000-square-foot museum featuring contemporary art exhibitions and a cultural center.

Looks like you’re traveling with a smaller group

Our Private Trips are best for groups of 6 or more. We suggest joining a scheduled trip.

Please Select a Group Size

Group size is required to show per-person pricing. Your group size can be approximate and can change.

Activity Level: 2-4

Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. Several routes and a range of levels are offered each day so you can choose how much or how little activity you want to do. Learn more about how we determine activity levels.

Route notes

Kentucky's landscape is characterized by constant rises and valleys, and the continuously rolling terrain can make routes feel more challenging than the mileage may suggest. There are no flat sections of riding on this trip.

Daily Route Options

* Includes shuttle.
Day 1
Level 2 | 25 miles | 1600 ft. gain
Level 3 | 36 miles | 2300 ft. gain
Day 2
Level 2 | 27 miles* | 1400 ft. gain
Level 3 | 35 miles* | 2100 ft. gain
Level 4 | 54 miles | 3500 ft. gain
Day 3
Level 2 | 16 miles* | 1500 ft. gain
Level 3 | 35 miles* | 2000 ft. gain
Level 4 | 55 miles | 3500 ft. gain
Day 4
Level 2 | 27 miles* | 1600 ft. gain
Level 3 | 35 miles* | 1900 ft. gain
Level 4 | 46 miles | 2300 ft. gain
Day 5
Level 1 | 17 miles* | 600 ft. gain
Level 2 | 28 miles | 1000 ft. gain

What's Included

Available Bike Options

The key to a stellar day's ride is a bike that's perfectly in tune with your cycling style… Backroads has you covered with the best bike fleet in the world! Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Click the arrow to see all bike options.

Backroads Performance Road Bike
Backroads Performance Road Bike
Performance Road Bike

Included in your trip price

This custom-designed titanium bike is lightweight and responsive, featuring Shimano Ultegra Di2 electronic shifting, 11-speed compact gearing, a premium Mavic Ksyrium Pro wheelset and a full carbon fork. 

Backroads Touring Bike
Backroads Touring Bike
Touring Bike

Included in your trip price

A proven classic, this custom-designed titanium bike is suited for a wide range of cyclists. It features a comfortable ergonomic seat and a long wheel base that add to the bike’s control and stability.

Backroads Electric-Assist Bike
Backroads Electric-Assist Bike
Electric-Assist Bike

Included in your trip price

Keep pace or zip ahead, pedaling with an electric boost. This bike provides plenty of power to flatten the hills and more than enough battery range to cover the distance.
Min. age to ride e-bike: 16+

Canyon Endurace SLX 9 Di2
Canyon Endurace SLX 9 Di2
Canyon Endurace SLX 9 Di2

Ride like a pro with the top-of-the-line carbon Canyon Endurace CF SLX 9 Di2. A performance-first flagship endurance bike engineered for comfort and race-level riding.

$650 rental fee; subject to availability

Co-Motion Torpedo Tandem Bike
Co-Motion Torpedo Tandem Bike
Tandem Bike

This hand-built frame features Co-Motion's custom-designed cro-moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train, and a custom, upgraded wheelset. For experienced tandem riders.
$400 rental fee

Also Included

  • All breakfasts, 5 lunches and 4 dinners
  • Expertise and services of our experienced Trip Leaders
  • Snacks and beverages between meals
  • Additional guides and experts from the region on many trips
  • Van shuttles to support a variety of route options
  • Comprehensive Travel Planner with detailed pre-trip information
  • Private guided tours at museums, historic sites, wineries and other select attractions as noted in the Travel Planner
  • All gratuities at hotels and restaurants
  • Special events, including wine tastings and other select attractions as mentioned in the Travel Planner
  • On biking and multi-adventure trips, use of fully equipped Backroads titanium bike plus helmet and accessories
  • Trailercycles, carriers, and kid-sized helmets for Family Trips
  • Equipment and experienced guides for kayaking, rafting, snorkeling, sailing and canoeing as described
  • Park and other entry fees
  • Fares for trains, ferries and other modes of travel as listed in the Travel Planner
  • Select coach transfers
  • Baggage transfers and porterage

Straight talk

We want to make sure you're on the right trip and that you have the best experience possible. Every Backroads trip is unique and this one is no exception.

Roads & Traffic

Kentucky is filled with scenic country roads; however, many of them are narrow and lack a proper shoulder. On some occasions we have to bike on short sections of busier road to connect the best biking routes. Of course, you're always welcome to jump in the shuttle to avoid the more trafficked sections.


On the first night of the trip we stay at the Shaker Village Inn, a Casual Hotel. This historic hotel is purposefully designed in a minimalist style that reflects the Shaker philosophy. This means simple rooms with fewer amenities than one might find at a typical Backroads hotel. 

Ask a trip expert

Have a question and need expert advice? Our team of Trip Consultants is here to help! You can also visit our Help Center.

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