Kentucky Bike Tour
The 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.
THIS ITINERARY: 5 days, 4 nights
ACCOMMODATIONS: Premiere Hotels*
Start Louisville / End Lexington or Louisville
Start/End locations may vary. Do not book flights until your trip details are confirmed.
- Follow 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
5 Days Premiere Hotels*
From Louisville, venture to true bluegrass country where our journey begins | Spin 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 US | Join a private tour of the farm before a down-home dinner of Kentucky dishes made with ingredients from Shaker Village's garden.
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.
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 and grazing horses | Visit boutique distilleries and taste their small-batch bourbon.
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.
Ride through pastureland dotted with stables and Thoroughbreds near Lexington, often called the Horse Capital of the World | Engage with the four-legged residents of the Kentucky Horse Park, a working horse farm with museums and an equine theme park | 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 local's favorite route, followed by a visit to a historic distillery.
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.
The earlier you book, the more choice you'll have and the lower your price. And you can always change your mind — you won't be charged to transfer to a different trip before your final payment is due. View cancellation policy
Click on dates for pricing, itinerary variations and to book your trip. Price is per person, double occupancy.
Activity Level: 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. LEARN MORE.
Note: 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.
Available Bike Options
- 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
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.
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.