
Kentucky Bourbon Country Bike Tour
Couples, Friends & Solos
Kentucky Bourbon Country Bike Tour
Couples, Friends & Solos
5 days
4 nights
Activity Levels 2-4
Premiere Hotels
2025: Apr-Jun, Sep-Oct2026: Apr-Jun, Sep-Oct

A Legendary Trail from Louisville to Lexington
Kentucky's bluegrass landscape nurtures prized Thoroughbreds and inspires musicians. Bourbon is carefully crafted here. And Southern hospitality nourishes its welcoming culture.
Highlights
- Bike the Kentucky Bourbon TrailĀ® 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 Stateāfrom a historic Shaker community to traditional bluegrass music
- Live like royalty at the Kentucky Castle and stay at a hip museum hotel in Lexington

StartLouisville
EndLexington or Louisville
* Start/End locations may vary. Do not book flights until your trip details are confirmed.
Itinerary

Day 1
From Louisville, venture to true bluegrass country, where our journey begins ā¢ Bike through rolling farmland, wooded areas and peaceful country roads ā¢ History unfolds in Harrodsburg with buildings dating back to the 1850s ā¢ Stay in Shaker Village, a beautifully restored historical campus and thriving heart of a bygone utopian community ā¢ Join a private tour of the farm before a down-home dinner of Kentucky dishes made with ingredients from Shaker Village's garden.

Night 1
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 ā¢ Journey to Frankfort, the stateās charming riverside capital city boasting a downtown rich in culture and historical architecture ā¢ Make yourself at home at Kentucky Castle, a striking medieval-inspired hotel complete with stone walls and turrets plus its own working farm ā¢ Enjoy a bluegrass performance while savoring Southern cuisine ā¢ Follow postcard-perfect country lanes past expansive estates, grazing horses and boutique distilleries ā¢ Explore a historic distillery ā¢ 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.

Nights 2-3
Named the āMost Beautiful Hotel in Kentuckyā 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 ā¢ Take time to wander around the exhibitions at our boutique hotelās contemporary art museum ā¢ Savor one last ride along a favorite route of locals.




Night 4
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.
What's Included
See moreStraight 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.
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, youāre 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.
Hotels
World-Class Hotels
Our hand-selected Premiere hotels offer exceptional hospitality and experiences as special as the regions we explore.
ļ»æHotels may vary based on departure. Any variations will be displayed when selecting a departure under Dates & Prices.

Night 1
*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
Premiere Hotel
Named the āMost Beautiful Hotel in Kentuckyā 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
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.
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#MyBackroadsTrip
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.

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

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

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
- Limited availability on Unplugged Bike Tours; learn more
Min. age to ride e-bike: 16+

- $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.
Review Snapshot
by PowerReviews
Reviewed by 21 customers
Beyond our expectations
Everything was excellent about our trip. Our leaders were exceptional. The accommodations were fantastic. The food was of supreme quality and abundance. Thankfully, we were biking thru gorgeous scenery and well planed routes to help burn the calories from all the food. Backroads exceeded every expectation we had about every detail of our trip. Can't recommend then high enough!!


Our trip exceeded expectations!
The Backroads Leadership was terrific! Great leadership and support, they made sure that everyone had a very memorable holiday. Great Job!


Bucket List trip - Fantastic. Don't wait - Do it!
Kentucky is a beautiful, lush green state that has to be seen to be believed and yes, has lots of rolling hills. No worries, use a pedal assist bike, a first time rider can do it ( like me, almost 70). Bike is easy to adapt to, clear navigator on bike to keep you on track, biking at your own pace. Trip leaders made the experience seamless and add lots of fun with their enthusiasm and knowledge. Interesting hotels, good food, snacks and bourbon if you like,
LOVED IT!!
Incredible views, and the best biking routes you could ask for. We all want to do it again. Especially loved the Shaker Villageā¦.what a peaceful, lovely place to stay. Guides were terrific. And loved meeting the horses. Thanks Backroads!

Kentucky was wonderful!
Wow! Just....wow! You quickly run out of superlatives when trying to describe this experience! We loved the rides! The flow of each day is well planned. The scenery is spectacular! It is full of green rolling hills, stone and black board fences, horses, palatial barns, mansions, and small butter-smooth roads. The accommodations run the gamut of simple elegance at Shaker Village, to European poshness at Kentucky Castle, to artful edginess at Hotel 21-C. All beautiful; all comfortable; all well-managed. Meals were very special, and every breakfast, lunch, and dinner was provided. This is not true on every trip. We especially lucked out with our trip leaders. Joey Coe (a Kentucky native) is the person who did the research and layed-out the rides for the entire trip years ago, and has continued to tweak and update the rides annually. Emma Silver has adopted Kentucky as her current base of operations due to her love of the state. They were both wonderful ambassadors for all that's Kentucky. Both of these trip leaders go to eleven! This is just a wonderful ride! We did it three and a half years ago, and it has only improved. Great having a world class ride in the heartland of America. No passport needed! There is very little flat land on this trip. Unless you are a very strong rider, e-bikes are recommended. Hope y'all get meet Orville at Shaker Village. Biggest ham of a turkey ever! Please do this ride. you will not be disappointed!
Terrifc Trip - Made Better by Leaders
This was my third Backroads trip and they have all been staffed by excellent people. How in the world are you able to find so many terrific people? Your selection and training process must be the best in corporate America. Joey was so great! Calm professional leadership with a hard work ethic. I know he works in Corporate but let him continue to runs a couple of trips per year - good policy to keep HQ in touch with the field. Emma also was... simply extraordinary. 21c had cool rooms and the best dam old fashioned I've ever had.
The BEST!
As always...your leaders MAKE or break a trip. Peter, Joey and Naomi MADE IT!! Please thank our leaders from me. Peter was The BEST you could ever hire. Tender, smart, kind, responsive. Totally rescued me when my pedal fell off. Joey was so in-tuned to each one of us. He has a great sense of humor and made a point of giving equal attention to each guest (and there were 14 of us). Very cool man. it all comes down to your ability to pull us all out of our comfort zones while making us feel special and have fun.
Biking and Bourbon - two of our favorite things!
Excellent experience all the way around! Our bike trip leaders, Emma and Rayna, and their support from Abby and Dara, were fabulous. Upbeat, motivating and so accommodating! A fine group of young women! The attention to detail that this company provides is superb, from pre-trip communication to delivering us back to our hotel at the end of the trip. All of meals and accommodations were first rate. Fabulous job, keep up the great work!
Our trip to The Kentucky Back roads was breathtaking !!
Rayna , Emma and Justin went out of their way in every way possible to make this trip fantastic .
The best way to see the Kentucky Landscape
This was the first Backroads trip for my husband and I can not say enough. First , the trip leaders were fantastic. TEAM Justin, Rayna and Emma were absolutely wonderful. They encompass the true meaning of a TEAM. From day one to the very end they all worked tirelessly to ensure everyone had a great time. Justin -you rock and made me laugh daily. Rayna- your bubbly personality is infectious and Emma- your the tug boat that we all needed , thank you for waiting for me ! You all get a 100!
Dates & Prices
Dates & Prices
Click on dates for pricing, itinerary variations (if any) and to book your trip. Price is per person, double occupancy in USD.
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