Kentucky Bike Tour

Couples, Friends & Solos

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Older Teens & 20s Best for ages 17-23 (min. age 14)

Families with Teens & Kids Best for ages 9-17 (min. age 4)

From $3,499 - $3,799 /person

5 days

4 nights

Activity Levels 2-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Premiere Hotels

Premiere Hotels - From lavish luxury to on-trend boutique, offering experiences as unique as the regions we explore.

Casual Plus Hotels - A step above Casual but not quite Premiere.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

Kentucky Bike Tour

Couples, Friends & Solos

Small Group Adventures for:

Couples, Friends & Solos Adults 18+

Women's Adventures Women 18+

Families with Young Adults 20s & Beyond Best for ages 20+ (min. age 18)

Families with Older Teens & 20s Best for ages 17-23 (min. age 14)

Families with Teens & Kids Best for ages 9-17 (min. age 4)

5 days

4 nights

Activity Levels 2-4

We categorize our trips based on a range of activity levels from leisurely (1) to avid (5) with plenty of options in between.

Premiere Hotels

Premiere Hotels - From lavish luxury to on-trend boutique, offering experiences as unique as the regions we explore.

Casual Plus Hotels - A step above Casual but not quite Premiere.

Casual Hotels - Known for their character, charm and proximity to outdoor adventures and Backroads activities.

Small Luxury Ships - Unpack once and cover more distance on an intimate ship with spacious staterooms and superb amenities.

2024: Jun, Sep-Oct 2025: Apr-Jun, Sep-Oct

From $3,499 - $3,799 /person

Legendary Bourbon Trail™ - Louisville to Lexington

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.

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Highlights

  • 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
Kentucky Bike Tour map

Kentucky

Start Louisville

End Lexington or Louisville

Airports & Travel details*

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

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Itinerary

Day 1

Description

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, a beautifully restored historical campus and thriving heart of a bygone utopian community • Join a private tour of the farm before a down-home dinner of Kentucky dishes made with ingredients from Shaker Village's garden.

Accommodations

Night 1

Shaker Village Inn
Harrodsburg
*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.

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Days 2-3

Description

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 • 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.

Accommodations

Nights 2-3

Kentucky Castle
Versailles
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)

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Days 4-5

Description

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 • 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. 

Accommodations

Night 4

21C Museum Hotel
Lexington
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.

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

What's Included

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Straight Talk

We want to make sure you're on the trip that's right for you. 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.

Accommodation
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. 

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

Download Itinerary

From $3,499 - $3,799 /person

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Hotels

World-Class Hotels

Our hand-selected Premiere hotels offer exceptional hospitality and experiences as special as the regions we explore.

Hotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Night 1

Shaker Village Inn
Harrodsburg

*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.

Nights 2-3

Kentucky Castle
Versailles

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)

Night 4

21C Museum Hotel
Lexington

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.

From $3,499 - $3,799 /person

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Bikes

Choose Your Perfect Bike

Our bikes are designed and built with specific cyclists and riding styles in mind, so we can always offer you a perfect ride. Please note that bike requests are subject to availability and prioritized based on the date they're submitted.

Backroads Performance Racer 2.0
Backroads Next Generation Performance Road Bike

Included in your trip price

  • Ideal for avid cyclists
  • Redesigned for 2024
  • Next gen titanium frame with carbon wheels
  • Responsive, efficient and comfortable
  • Drop handlebars only
Backroads Touring Bike
Backroads Touring Bike

Included in your trip price

  • Suited for a wide range of cyclists
  • Comfortable ergonomic seat
  • Long wheel base adds to the bike's control and stability
  • Upright handlebars only
Backroads Electric-Assist Bike
Backroads Electric-Assist Bike

Included in your trip price

  • One of the lightest e-bikes available
  • Provides plenty of power and more than enough battery
  • Lower top tubes for easier mounting and dismounting
  • Upright handlebars only

Min. age to ride e-bike: 16+

Canyon Endurace SLX 9 Di2
  • $650 rental fee; subject to availability
  • Ride like a pro with the top-of-the-line carbon Canyon Endurace CF SLX 9 Di2
  • Perfectly balanced comfort and performance with a Grand Tour pedigree
  • State-of-the-art components and precision German engineering
Co-Motion Torpedo Tandem Bike
Tandem Bike
  • $400 rental fee
  • Hand-built frame features Co-Motion's custom-designed Cro-Moly steel tubeset, powerful Avid disc brakes, Shimano Ultegra drive train
  • Custom upgraded wheelset
  • Best for riders with some tandem experience.

From $3,499 - $3,799 /person

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From $3,499 - $3,799 /person

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Dates & Prices

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.

Want to learn more about this trip?

Request a Detailed Itinerary! Complete with descriptions of each day, tips on travel arrangements, regional highlights and more, it’s the perfect tool to help you choose. You can easily share it with friends too!

Download Itinerary

Book with Confidence

Backroads provides flexible booking policies so that you can plan your vacation with complete peace of mind.

Learn more

From $3,499 - $3,799 /person

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