Cycle Of Life Adventures
Kentucky Four Day Custom Bike Tour
Registration Open
Custom Recreational

Kentucky Four Day Custom Bike Tour

Behold beautiful landscapes and animals ... book today!

Dates
May 1 – May 4, 2027
Duration
4 days
Starts
Lexington, KY
Ends
Lexington, KY
Group Size
6–12 riders

Route Map

About This Tour

This 4-day Kentucky cycling and social event is designed for rider levels from recreational to advanced. The design of this tour keeps us in north Lexington, Kentucky, for all four nights. We will ride quiet, one-lane roads in great little towns near Versailles, Woodford, Georgetown, Paris, and Lexington.

The group size is best if kept between 8-12 riders

The Kentucky Horse Country is an ideal cycling location. Lexington is less than an 8-hour drive from some of the larger population centers east of the Mississippi. Some of these cities include: Chicago, Indianapolis, Pittsburgh, St. Louis, Atlanta, and Nashville.
The land's topography is "rolling". So, coasting down one hill often carries you near the top of the next. Central Kentucky is rich in limestone, which contributes to the lush Bluegrass, clean, fresh water, and the ideal environment for the thoroughbred industry. In a 35-mile radius of Lexington, there are more than 500 thoroughbred horse farms. Every ride takes you past miles of fenced pastures and many magnificent creatures.
The wonderful water quality also makes for some of the best distilled “spirits” in the world. In and around Bourbon County, KY, are dozens of distilleries, all of which offer tours of their manufacturing facilities led by colorful guides. Their processes are similar, but their products all taste a bit different. Have fun, try a tasting, but don’t drink and ride.

Tour Highlights

Group breakfast at the Keeneland Racetrack track kitchen on morning two.
A Bourbon tasting tour at Woodford Reserve.
A guided “Unique Horse Farm Tours” by Shawn Washington. Not to be missed!
Additional information for local attractions.
Every day will include shorter casual ride options and “advanced” longer ride options.
Distances can vary from 15 miles of touring to a choice of century rides.
This tour qualifies for a 5% discount for returning guests or for groups of 4 or more.

Minimum Group Size
6 guests 
Travel & Lodging Logistics

Fly in and out of Lexington Bluegrass Airport.
Arrive to the starting hotel for cocktails and dinner by 5pm on May 18

Accommodations

We will stay all 4 nights at the GLo – Best Western now the Holiday Inn Express

Other

Event Highlights: Unbelievable riding, distillery tour, horse farm tour. Additional information for local attractions. 
Available Mechanic (tipping suggested).
Ride with GPS mapping available upon registration. Rides may vary slightly if construction or closures occur. Click on a route in the map below to see mileage and elevation.

Day-by-Day Itinerary

67.00 miles

Short Ride: Lexington – Versailles – loop – shuttle to Woodford Reserve Bourbon Tasting Tour (1pm) Long Ride: Lexington – Versailles – Woodford loop (67 miles)

60.00 miles

Short Ride: Lexington – Paris – Lexington Loop (35+ miles); Afternoon available for your choice of activities in town – shuttle available to Wild Turkey Distillery Long Ride: Lexington – Winchester – Paris – Lexington (60 miles)

16.00 miles

Short Ride: Lexington – Legacy Trail – Horse Park and back (16 miles); Tickets for Unique Horse Farm Tours are complimentary Long Ride: Lexington – Legacy Trail – Georgetown Loop (47 miles); 3:00 PM Memorial Day Picnic at the Kentucky Horse Park

25.00 miles

Short Ride: Lexington – Keenland – Calumet Loop (25 Miles) Long Ride: Lexington – Keeneland – Midway – Versailles – Lexington (70 miles)

What's Included

Included

  • All maps and GPS routing
  • Van support at 5-15 mile intervals
  • Mechanical support (tipping suggested)
  • Energy drinks and riding snacks.
  • A casual catered dinner and a complimentary Wine and Brew social on our first evening.
  • An occasional van ride for those who are tired.
  • One Group Activity

Not Included

  • One dinner 
  • Airfare
  • Souvenirs
  • 12% gratuity for guides, mechanics, volunteers and tour staff is not included, but greatly appreciated
Regions
$2,100 per person
Registration Open
Tour dates May 1 – May 4, 2027
Duration 4 days
Lodging Included
Deposit to hold spot $315
Single room supplement +$350

Spots are limited — reserve yours with a deposit.

Bike rental & helmet available as add-ons

Ready to ride Kentucky Four Day Custom Bike Tour?

Questions about this tour? Our team is happy to help you plan the perfect trip.