Kentucky Horses and Bourbon – May 6-13 and May 13-20, 2026

Trip Summary

7 Nights
Avg miles per day: 30-50
Hill profile: Some hills.
Some rollers.

Cost: TBD

Join us for this new Adventures in Tandem tour. The Lexington, Kentucky area is known for its horse farms and racetracks, bourbon distilleries and of course, its southern hospitality. It is also known to have great bicycling. It is the closest thing to rolling hills that we know of.

We plan to open this tour in late spring 2026. If you are interested in this tour, please check the I’m Interested button on the right and you will get an email announcing when the tour opens.

 

The following is a draft itinerary:

Day 1 We start the tour in Lexington, Kentucky, known as the “Horse Capital of the World”. We will meet in the early afternoon and we will offer a short ride outside of town along horse pastureland. We will enjoy a group dinner.
Day 2 After breakfast at the hotel, we will go on a loop ride through the beautiful, quiet roads. If you drove to the start, we will have you re-park your car at the nearby Lexington airport. We will give you a lift back to the hotel. Dinner is on your own in one of the many restaurants within walking distance of the hotel.
Day 3 We leave Lexington, enroute to the sweet town of Versailles. Our group will be spread between two lovely country bed and breakfasts. We will enjoy a group dinner in Versailles.
Day 4 We will offer a loop ride today, or you can just relax in town. You could even take a ride over the the Kentucky Castle in the morning for some goat yoga! In the late afternoon, we will take a group thoroughbred horse farm tour followed by a group dinner. On the tour you will be able to interact with the farm horses and maybe even see foals with their moms.
Day 5

The Buffalo Trace Distillery in Frankfort

Today we will offer another loop ride around the bluegrass countryside. The loop will take you up to the city of Frankfort and along the Bourbon Trail with a distillery tour at the Buffalo Trace Distillery. Dinner is on your own at one of the many restaurants in Versailles.

Day 6 After our last sumptuous breakfast at the Inns, we leave take a short transport to the Four Roses Distillery where we will start our ride to Shakertown. In Shakertown, we will stay inside the Shaker Village of Pleasant Hill which at one point was the third largest Shaker community in the US. We will have a private guided tour of the Village. We will enjoy a group dinner at the Shaker Village.
Day 7 We will offer a loop ride to the town of Danville where you can enjoy lunch and see the glass exhibit at the Centre College and Art Center, or you can relax and take in the Shaker Village and Farm. You can explore additional areas of the Village through self-guided as well as guided tours. We will enjoy our last group dinner at the Village.
Day 8 Our tour ends after breakfast.

As with most of our tours, we limit the size of the tour to a maximum of ten couples. We plan to open this tour in mid-2025. Please click below if you are interested in this tour. We will let you know as soon as the tour opens.

Here is what is included in the tour:

  • 7 nights lodging.
  • 7 breakfasts and 5 dinners
  • Routes. Daily mileage will range from 30 to 60 miles
  • Luggage transport
  • Bike and bus transport on Day 6
  • SAG support
  • Tandem bike case storage, if needed
  • Entrance into the Shaker Village
  • Horse farm tour
  • Bourbon tour and tasting
  • Transportation from the Lexington Airport if you drove to the start. (You will need to repark it for the tour.)
  • Transportation to retrieve your car, if you drove to the start of the tour

 

Who knows?!! You might even see a camel!

What is not included:

  • Transportation to the start point
  • Meals, other than those mentioned above
  • Alcoholic beverages
  • Admission to points of interest not referenced above

Note that we do not provide any bicycles. We expect that you have a tandem that is in good working order and that you are able to assemble your bike. If you do not have your own tandem, you can rent a coupled tandem from Mel at Tandems East. Mel also sells tandems, so if you end up renting from him, you might get a discount if you purchase a bike from them. If you have a tandem that is not coupled, it is possible to bring it, but you should make sure that all of your flights could handle the larger box. 

What is the average mileage per day?

As there is a lot to see each day, average mileage will be in the 30-50 mile range. We can certainly add routes for those that would like to do more riding. We can also shorten some days if you want. There are some hills — just let us know what you like!

While this can change, this is where we plan to be staying:

21C Museum Hotel

Rose Hill Inn or A Storybook Inn

Shaker Village of Pleasant Hill