From Louisville, venture to true bluegrass country, where our journey begins • Bike through rolling farmland, wooded areas and peaceful country roads • History unfolds in Harrodsburg with buildings dating back to the 1850s • Stay in Shaker Village, a beautifully restored historical campus and thriving heart of a bygone utopian community • Join a private tour of the farm before a down-home dinner of Kentucky dishes made with ingredients from Shaker Village's garden.

Ride an undulating route passing rushing rivers and verdant hillsides dotted with barns and lined with stacked stone walls • Journey to Frankfort, the state’s charming riverside capital city boasting a downtown rich in culture and historical architecture • Make yourself at home at Kentucky Castle, a striking medieval-inspired hotel complete with stone walls and turrets plus its own working farm • Enjoy a bluegrass performance while savoring Southern cuisine • Follow postcard-perfect country lanes past expansive estates, grazing horses and boutique distilleries • Explore a historic distillery • Get an incredible behind-the-scenes look at one of the world's premier Thoroughbred race farms and see a few celebrity horses, including winners of the Kentucky Derby.

Bike through pastureland dotted with stables and Thoroughbreds near Lexington, often called the Horse Capital of the World • Take time to wander around the exhibitions at our boutique hotel’s contemporary art museum • Savor one last ride along a favorite route of locals.