Kentucky Bluegrass Cycling Tour

Starting From


Number of days


Start Location

Lexington, KY

End Location

Lexington, KY

Group Size




Operated by

Timberline Adventures

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Spring in Bluegrass country is an excellent break from winter, refreshing and fascinating.  The beautiful, rolling, pastoral countryside, the grand, historic horse farms, the deep historical and cultural legacy, and the region’s excellent cycling roads are the ingredients for an exciting and rewarding cycling adventure.  When you figure in the prodigious line up of inns and restaurants, the Kentucky Bluegrass Country becomes a one-of-a-kind experience.

Operated by:

Timberline Adventures

Every day is special, with room to breathe, ample exercise, amazing vistas, delicious meals and new friends. You’ll never be pressured to keep up or hold back. It's your tr...

Additional Information

May 12 - 18, 2019

Kentucky is a land of profound natural beauty—it’s a land of mountains, lakes, forests, rivers and magnificent, lush rolling countryside. We’ve chosen the Bluegrass region of north central Kentucky as the focus for our Kentucky Bluegrass cycling tour.


  • Ride through beautiful Bourbon County, home to some of the world’s greatest thoroughbred horse farms—the breeding grounds for racehorses like Secretariat and Riva Ridge
  • Pedal through Fort Boonesborough State park, site of the fort constructed by Daniel Boone on the banks of the Kentucky River in 1775.
  • Visit Berea, the arts and crafts capital of Kentucky, which boasts over 150 antique shops and more than 40 crafts workshops
  • Explore Danville, the original capital of the Kentucky District of Virginia and a major trading center on the Wilderness Road that extended westward from Cumberland Gap
  • Stop at Perryville Battlefield State Historical Park, site of a major Civil War battle in 1862
  • Ride through Bardstown, home to four noted bourbon distilleries and is the repository for the legend of “good old Kentucky bourbon” and My Old Kentucky Home State Park
  • Stay at iconic inns and B&Bs


Day 1:  Arrive, assemble, van transport, bike fitting, orientation dinner

Day 2 (55 miles):  Ride through Bourbon Conty and on to Winchester

Day 3 (46 miles):  Ride south to Ft. Boonesborough State Park, then to Berea

Day 4 (67 miles):  Ride from Berea to Danville, and Perryville Battlefield State Historical Park, then on to Harrodsburg

Day 5 (56 miles):  Harrodsburg to Bardstown

Day 6 (62 miles):  Ride east through Lawrenceburg to Versailles

Day 7 (21 miles);  Versailles to Lexington


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