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Kentucky Bluegrass

Explore the birthplace of America’s western frontier on a cycling tour through Kentucky’s Bluegrass region, where rolling pastoral landscapes, historic horse farms, Civil War sites, bourbon distilleries, and rich cultural heritage create an unforgettable ride through Southern charm and frontier legacy.

Average Climate

No upcoming dates are currently available for this trip.

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Double Booking TBD

Single Booking TBD

Roommate Rebate TBD

Trip Type

Cycling

Difficulty Level

3

Trip Length

7 Days, 6 Nights

Distance

310 Miles
498.9 Kilometers

Meeting Time

Airport 2:30 pm, Hotel 3:00 pm

Drop-off Time

4 pm

Assembly Point

Lexington, KY

Inclusions

Includes all lodging, breakfasts, dinners, leaders, snacks, support van, park entrance fees, airport transfers, Ride With GPS Experience, tour maps and narratives.  Timberline van shuttle is included to and from Lexington, KY.

Not Included: Airline Service; Guide Gratuity, Horse Farm and Distillery Tours

Bonus Tours

Have questions? We’re here to help! Call us at 303-664-8388 or reach out online.

Contact For Details

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.

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.

ITINERARY

Day 1: Arrive, assemble, van transport, bike fitting, Orientation Dinner

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Meals: Dinner

Day 2: Ride through Bourbon County and on to Winchester

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Meals: Breakfast, Dinner

Distance: 51 miles

Elevation Gain: 2,290 feet

We’ll assemble in Lexington, the heart of Bluegrass Country, and ride from the city on Day 2 through Fayette 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 ride past one of the world’s great racetracks at Keeneland where a Morning Works tour is possible. We work our way around Lexington to Paris, then ride south to Winchester, where we’ll spend the evening.

Day 3: Ride south to Ft. Boonesborough State Park, then to Berea

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Accommodation: Boone Tavern

Meals: Breakfast, Dinner

Distance: 45 miles

Elevation Gain: 2,445 feet

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.

Day 4: Ride from Berea to Danville, and Perryville Battlefield State Historic Park, then on to Harrodsburg

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Accommodation: Beaumont Inn

Meals: Breakfast, Dinner

Distance: 68 miles

Elevation Gain: 3,675 feet

From Berea on Day 4, 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 continue on to the Perryville Battlefield State Historic Park, site of a major Civil War battle in 1862. After a stop there, our route ends up in Harrodsburg, founded in 1774 as Kentucky’s first permanent settlement. We have an option to visit the Shaker Village of Pleasant Hill north of Harrodsburg, before spending the evening in the grand historic Beaumont Inn.

Day 5: Harrodsburg to Bardstown

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Accommodation: Bourbon Manor B&B

Meals: Breakfast, Dinner

Distance: 54 miles

Elevation Gain: 2,990 feet

On Day 5, we’ll ride east from Harrodsburg through Springfield. We’re headed to Bardstown, 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”.

Day 6: Ride east through Lawrenceburg to Versailles

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Accommodation: Montgomery Inn

Meals: Breakfast, Dinner

Distance: 56 miles

Elevation Gain: 3,375 feet

More of the beautiful Bluegrass Country unfolds as we ride east through Lawrenceburg to Versailles on Day 6.

Day 7: Versailles to Lexington

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Meals: Breakfast

Distance: 36 miles

Elevation Gain: 2,260 feet

We’ll spend our final night in one of the elegant, historic bed and breakfasts in Versailles prior to our return to Lexington on Day 7. No need to rush through the last day of riding, as options to visit more horse farms, distilleries, and wineries abound, along with the Kentucky Castle and the Aviation museum. Eventually we will land in Lexington for the conclusion of our Kentucky Blue Grass tour.

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