Kentucky Bluegrass Cycling Tour

The inclusion of Kentucky Bluegrass Cycling Tour to Timberline's program was the natural extension of our career commitment to western bike trips. 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. Its 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, Kentucky never seceded from the Union, and, 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.

We've chosen the Bluegrass region of north central Kentucky as the focus for our Kentucky bike trip. The 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 extraordinary and rewarding cycling experience.

Our Kentucky Bluegrass Cycling Tour will 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 — the breeding grounds for the likes of Man O'War, Secretariat and Riva Ridge. As we ride from Lexington, we'll visit the historic Keeneland Race Course, have breakfast with the trainers and jockeys at the Track Kitchen and likely catch a few thoroughbreds during early morning workouts. We'll ride from Keeneland's back gate along the quiet roads lined with the magnificent Kentucky horse farms (estates!) for which this region is so well-known. We're headed for a visit to the Kentucky Horse Park, a great portrayal of Kentucky's thoroughbred culture. We'll spend the evening in Winchester and enjoy a great dinner at Hall's on the Kentucky River.

Early morning of Day 2, we'll bike 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 to the fascinating town of Berea, where we'll spend our second night in the historic Boone's Tavern Inn. 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 bike 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 west for a visit to Perryville Battlefield State Historical Park, site of a major Civil War battle in 1862. We'll tour the battlefield and then ride on to Harrodsburg, founded in 1774 as Kentucky's first permanent settlement. We'll visit the Shaker Village of Pleasant Hill north of Harrodsburg for dinner and spend the evening in the grand, historic Beaumont Inn.

On Day 4, we'll cycle 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."

More of the beautiful Bluegrass Country unfolds as we ride east through Lawrenceburg across the beautiful Kentucky River to Versailles on Day 5. We'll spend our final night in the elegant Montgomery Inn in Versailles prior to our return to Lexington. The Kentucky Bluegrass Cycling Tour will be one you will not soon forget!

Total Mileage — 245

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