Kentucky Bluegrass


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Includes all lodging, all breakfasts and dinners, park entrance fees, support van, leaders, tour maps & narratives.

Assembly Point

Lexington, KY

Timberline van shuttle is included to and from Lexington, KY.

Not Included: Airline service to Blue Grass Airport, Lexington, KY; Guide Gratuity

Meeting Time

Airport 3 pm, Hotel 3:30 pm

Drop-off Time

4 pm

“Love this group of guides and the group meals and conversations.” Jalena S.

Cycle Through America’s First Western Frontier

Spring in Bluegrass country is an excellent break from winter, refreshing and fascinating.  In so many ways, the Kentucky Territory was among the first of America’s western frontiers.  Hemmed in by the forbidding barrier of the Appalachians, Virginia settlers, hungry for land, finally breached the barrier at Cumberland Gap and soon asked that the federal government recognize their trans-Appalachian western settlement as the “free and independent state of the Commonwealth of Kentucky.”  In 1792, Kentucky became the first state west of the Appalachians to be admitted to the Union.
Kentucky’s historical and cultural heritage is rich and diverse.  It’s character and tradition, to a great extent, is southern, but at the same time exhibits the fierce, rugged mood of the western frontier.  It is the home of Daniel Boone and Henry Clay, and the birthplace of Abraham Lincoln and Jefferson Davis, born one year apart and within 140 miles of one another. Not surprisingly given its geographical position, Kentucky was a pivotal battleground during the Civil War.  Many key battles were fought on its soil, and its sons fought for both sides. Kentucky also is a land of profound natural beauty—it’s a land of mountains, lakes, forests, rivers and magnificent, lush rolling countryside.

Join Our Kentucky Bluegrass Cycling Tour!

We’ve chosen the Bluegrass region of north central Kentucky as the focus for our Kentucky Bluegrass cycling tour.  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.  The area is loaded with historical battlefields, distilleries where you can sip 40 year old Bourbon, and a prodigious line up of inns and restaurants, offering a one-of-a-kind cycling experience.

See Detailed Itinerary Here:

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Day 1Arrive, assemble, van transport, bike fitting, Orientation Dinner
Day 2Ride through Bourbon County and on to Winchester55
Day 3Ride south to Ft. Boonesborough State Park, then to Berea46
Day 4Ride from Berea to Danville, and Perryville Battlefield State Historical Park, then on to Harrodsburg67
Day 5Harrodsburg to Bardstown56
Day 6Ride east through Lawrenceburg to Versailles62
Day 7Versailles to Lexington21

Total Distance: 307 miles

Kentucky Bluegrass


(Contact Us to Request Dates)