Accommodations may vary based on departure date. Any difference from what is listed below can be found by clicking on your desired date on the View Scheduled Dates or Private Dates tabs.
Shaker Village Inn
Harrodsburg (1 night)
* 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.
Versailles (2 nights)
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.
21C Museum Hotel
Lexington (1 night)
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.
This Trip Is Rated Levels 2-4
Every Backroads trip is designed to appeal to a wide variety of interests and fitness levels. We know your pace may vary from one day to the next—and your traveling companion's may differ somewhat from yours. So we present a range of mileage options, and each day you decide exactly what and how much you want to do.
Daily Route Options (drag to see full )
|Daily Route Options
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.
* Includes shuttle.
Learn more about how we determine our activity level and fully support a range of abilities and interests.
Please note that our distance and elevation figures come from Ride with GPS. Other sources may give differing elevation figures due to different GPS and mapping technologies and other external factors.
All breakfasts, 5 lunches and 4 dinners
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! Read on for your available bike options for this trip.
Backroads Titanium Bikes (Included in your trip price)
Our custom-built titanium bikes are specially designed for you—and we offer different models for varied terrain so your bike is ideally suited to the region. Our custom-made bikes are included in your trip price.
Touring Bike (Included)
Performance Road Bike (Included)
NEW! Backroads Custom Electric-Assist Bike (Included in your trip price – Available beginning 4/1 in North America, 5/1 in Europe and 11/1 outside of Europe and North America.)
Our newly redesigned Titanium Electric-Assist Bike is a lightweight yet powerful machine unique in the world of e-bikes. It provides plenty of power (and then some!) to flatten the hills and more than enough battery range to cover the distance. Other outstanding features include the same comfort as our Touring Bikes and lower top tubes for easier mounting and dismounting.
Backroads Custom Electric-Assist Bike (Included)
Cannondale Pro Carbon Upgrade ($400 rental fee)
Delivering phenomenal acceleration and handling in a light and powerful package, the Cannondale 2020 Synapse Hi-MOD pro carbon upgrade is built for experienced cyclists, men and women alike, who are looking for a high-performance bike that doesn’t sacrifice comfort.
Cannondale 2020 Synapse Hi-MOD
Co-Motion Torpedo Tandem ($400 rental fee)
Do you prefer to spin in tandem with your partner? You'll love the Co-Motion Periscope Torpedo tandem on your Backroads trip. You can upgrade to a Co-Motion Torpedo Tandem on your trip.
Co-Motion Torpedo Tandem (Upgrade)
- 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
Get the Straight Talk about This Trip
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.
Why Travel with Backroads in Kentucky
The Best Leaders in Kentucky
Backroads has the best-qualified people to lead your trip in Kentucky, and our guests back that up, rating our Trip Leaders an average of 9.75 out of 10 for all-around quality of performance. Get the facts (and no fluff) on how we recruit and develop the very best people for your trip.
Quality You Can Measure
Since 1979, Backroads Founder and President Tom Hale has shown that staying #1 means constantly evaluating our performance using the best possible source of information: our guests. As we systematically analyze your feedback on our trip consultants, leaders, hotels, meals and on-trip activities, we never stop working to make a great company even better.
We've Set the Standard
For nearly four decades we've worked to earn and maintain our right to call Backroads the world's #1 active travel company. In pursuing that vision on behalf of our guests, we believe we've set the standard for our industry—captured in the Backroads Quality Guide, which clearly sets out the benchmarks of excellence, choice and support that we live by
We Know Where We're Going
Tom Hale has been keeping Backroads on track, with one eye on the horizon, since 1979. His passion for active travel, and for ensuring the highest-quality travel experience, is evident in every detail we add to make a guest's trip unforgettable—and the fact he's right there in the office, making it happen. To hear Tom describe his vision, watch our video.
A Variety of Routes Each Day
In Kentucky you head off each morning after choosing among several expertly designed routes—all with detailed directions, mileage and shuttle options. Unlike trips with one fixed daily route (or worse, one guide that everyone's obliged to follow), you're free to enjoy the best of the region at your pace, stopping wherever you want to explore further.
We Live in the Neighborhood
Our Trip Leaders in Kentucky live in the area and are deeply engaged in their communities, giving them unique inside knowledge they're happy to share in making your experience that much richer. They'll introduce you to people, customs and parts of town you'd likely never encounter on your own—and teach you a few local phrases to help break the ice.
Navigate Your Way in Kentucky
Your ride comes equipped with a GPS device, preloaded with all the routes and route options for your trip. If you prefer to bring your own device, we also have downloadable GPS files and of course, our good old paper directions are always available. Read more on why our navigation options are the best.
Great Bikes Included
Our custom-designed titanium bikes are best in class. From avid cyclists to easygoing riders, we believe that everyone deserves a seriously great bike to match their riding style. Learn more about our bike fleet.