Bikes, Bluegrass & Bourbon

Is there anything better than the charm of Kentucky's Bluegrass region on a fully supported cycling adventure through rolling countryside, historic horse farms, and world-famous bourbon country?

Ride scenic back roads that wind through the pastoral landscapes of Woodford County, Versailles, Frankfort, and Georgetown, where white-fenced pastures and thoroughbred horse farms define the scenery. Along the way, you'll have opportunities to explore everything the region has to offer.

Guests can join guided distillery tours, visit the beloved Old Friends Thoroughbred Retirement Farm after riding while discovering the culture, history, and hospitality that make the Bluegrass State such a memorable destination.

Optional tours of local distilleries are included

📅 Dates: October 14-17, 2027

🚴‍♀️Duration: 4 days/3 nights

🚴‍♀️ Distance: 35-60 miles per day

📍Locations: Woodford, Scott & Versailles Counties

💰 Cost: $2,695 (Double Occupancy) + $750 Single Supplement

What's Included:

  • 3 nights in upscale accommodations

  • Access to your car during the trip

  • Daily breakfast

  • 3 lunches & 2 dinners at locally owned, curated restaurants

  • 3 days of scenic cycling with fall foliage views

  • Support team and vehicles with water, snacks, and mechanical aid

  • Mobile mechanic at the back of the pack

  • Views of the Pastoral Farms

🌟 Highlights:

  • Kentucky’s Spectacular Fall Foliage is on full display

  • High-quality, local food

  • Quiet, lightly travelled roads

  • Picturesque equestrian homesteads

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Virginia’s Blue Ridge Adventure Tour

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Fall Foliage on the Greenbrier Trail