Kentucky Blue Grass Cycling Tour – 6 Day Self-Guided

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Double Booking


Single Booking


Roommate Rebate


Includes 5 nights lodging reservations with breakfast, recommendations for dinner and lunch, luggage transfer each day, tour maps, cue sheets and .gpx files, T-shirt, narratives about the area, 24x7 phone support on tour

Assembly Point

Lexington, KY


Arrive at: Blue Grass Airport, Lexington, KY

Optional Add-ons:  Pre and Post Tour Lodging Arrangements, Distillery Tours

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.

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.  Your stays include a prodigious line up of historic inns and B&B’s, making the Kentucky Bluegrass Country a one-of-a-kind experience.

This tour can be booked for any dates April through November.  We recommend a spring or fall date for the most pleasant weather.  Tours must be booked at least 2 weeks in advance, with a minimum of 2 participants.

(Note: actual hotels are subject to availability and not guaranteed before booking)


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

Total Distance: 307 miles

Kentucky Blue Grass Cycling Tour – 6 Day Self-Guided


(6 days, 5 nights)