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cycling trip Kentucky Blue Grass Cycling Tour Moderate

Dates: 5/7 - 13, 2017

(7 days, 6 nights; Sun. - Sat.)


Assembly Point: Lexington, KY

(Timberline van service is included from and to Lexington Blue Grass Airport, or use the hotel van shuttle)

Not included: Airline service to Lexington, KY; Guide Gratuity

Meeting time: 5/7 - airport 1 pm,
hotel 1:30 pm
Drop off time: 5/13 - 4 pm

Tour Cost: $2,275

Includes lodging, breakfasts and dinners, park entrance fees, van shuttles-support and snacks, leaders, trail maps and narratives.

Additional Single Occupancy Lodging Cost: $460

Inn Highlights

  • Boone Tavern
  • Baumont Inn

Spring in Bluegrass country is refreshing, lovely with a fascinating character to the region, an excellent break from winter.  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, though it never seceded from the Union, Kentucky, given its geographical position, was a pivotal battleground during the Civil War.  Many key battles were fought on its soil; its sons fought for both sides. Kentucky also is a land of profound natural beauty: 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 inaugural Kentucky Bluegrass cycling tour.  The beautiful rolling pastoral countryside, grand, historic horse farms, deep historical and cultural legacy, and the region’s excellent cycling roads are the ingredients for what we believe will be 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 1 to beautiful Bourbon County, home to some of the world’s greatest thoroughbred horse farms and 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 2, 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 more than 150 antique shops and more than 40 crafts workshops.

From Berea, we’ll ride 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 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 4, we’ll ride south from Harrodsburg to the Perryville Battlefield 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 5.  We’ll spend our final night in several of the elegant, historic bed and breakfasts in Versailles prior to our return to Lexington.


Pre-tour Arrive, assemble, van transport, bike fitting, orientation dinner  
Day 1 Assemble and ride from city to Bourbon County, home of some of the greatest thoroughbred horse farms (Lexington to Winchester) 55 miles
Day 2 Ride south to Ft. Boonesborough State Park, exploring some craft shops along the way (Winchester to Berea) 46 miles
Day 3 Ride from Berea to Danville, including a tour of some historic battlefields at Perryville Battlefield State Historical Park, then onto (Berea to Harrodsburg) 67miles
Day 4 Harrodsburg to Bardstown 56 miles
Day 5 Ride east through Lawrenceburg across the beautiful Kentucky River to Versailles (Bardstown to Versailles) 62 miles
Day 6 Versailles to Lexington, Once back in Lexington we will visit a Kentucky Bourbon Distillery for a tour 21 miles

Total cycling mileage - 326

Elevation Gains

Day 1

Day 2

Day 3

Day 4

Day 5

Day 6

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Routes, mileage and accommodations are subject to change due to safety, road/trail conditions, weather and availability.