Kentucky Blue Grass

Kentucky Blue Grass

May 12 - 18, 2019

(7 days, 6 nights; Sun - Sat)

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Family Friendly

Double Booking


Single Booking


Roommate Rebate


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

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 we st 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.  When you figure in the prodigious line up of Inns and restaurants, the Kentucky Bluegrass Country becomes a one-of-a-kind experience.

We’ll assemble in Lexington, the heart of Bluegrass Country, and ride from the city on Day 2 to beautiful Bourbon County, home to some of the world’s greatest thoroughbred horse farms—the breeding grounds for racehorses like Secretariat and Riva Ridge.  As we ride from Lexington, we’ll visit the world-renowned Kentucky Horse Park, a great portrayal of Kentucky’s world of horses.  From Paris, we’ll ride south to Winchester, where we’ll spend the evening.  Early morning of Day 3, we’ll ride south to Fort Boonesborough State park, site of the fort constructed by Daniel Boone on the banks of the Kentucky River in 1775.  We’ll continue south through Richmond to the fascinating town of Berea, where we’ll spend our second night.  Regarded as the arts and crafts capital of Kentucky, Berea boasts over 150 antique shops and more than 40 crafts workshops.

From Berea, we’ll ride to the west to 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. We’ll continue on to Harrodsburg, founded in 1774 as Kentucky’s first permanent settlement.  We’ll visit the Shaker Village of Pleasant Hill north of Harrodsburg and spend the evening in the grand historic Beaumont Inn. On Day 5, we’ll ride south from Harrodsburg to the Perryville Battlefield State Historical State Historical Park, site of a major Civil War battle in 1862.  We’re headed to Bardstown on this day, and a visit to My Old Kentucky Home State Park.  Bardstown also is home to four noted bourbon distilleries and is the repository for the legend of “good old Kentucky bourbon.” More of the beautiful Bluegrass Country unfolds as we ride east through Lawrenceburg to Versailles on Day 6.  We’ll spend our final night in one of the elegant, historic bed and breakfasts in Versailles prior to our return to Lexington.


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

Inn Highlights

  • Boone Tavern
  • Beaumont Inn

Kentucky Blue Grass

May 12 - 18, 2019

(7 days, 6 nights; Sun - Sat)