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The weekend begins with fun and festivities on Friday featuring optional rides throughout the Bluegrass Region with the Bluegrass Cycling Club, a large number of cycling related vendors, food trucks and entertainment.

Saturday is the flagship day with five route choices ranging from 26 miles to the iconic Century. On Sunday you have your choice of four rides ranging from 21 – 74 miles. On either day you will wind your way through and around the Bluegrass region and be treated to some of the most beautiful scenery you can imagine including horse farms, stone fences, rivers, streams, lush pastures, historic towns, and bourbon distilleries.

The ride is fully supported with frequent rest stops featuring nutritional, as well as delicious, items chosen to fuel your ride.


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Always a professional event. My favorite of the Kentucky Challenge. Looking forward to next year. Could you hold two per year?

All the volunteers I encountered were friendly and helpful and did a terrific job!  Route selection was excellent with great road markings. Rest stops were well placed and filled with great snacks.

Beautiful countryside, low traffic, courteous drivers, friendly participants, excellent volunteers, many ride options. Our favorite of all rides!

Very well organized. Great support with sag vehicles clearly, frequently visible. Great volunteers, so friendly and helpful. Great group of riders, friendly and nice. This is my 4th time and I’ll be back. I rode by myself as all my friend riders had to bail for various reasons. I am glad I came and rode. Beautiful country, great support, and enthusiastic riders.

from the horse's mouth

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Central kentucky

About the

Welcome to Kentucky, where rolling bluegrass meets the thrill of the open road. Nestled in the heart of horse country, this vibrant area isn’t just for equestrian enthusiasts – it’s also a haven for cyclists.

For those seeking a challenge, the gently rolling hills provide the ideal terrain for a satisfying workout. Cyclists can revel in the beauty of the countryside, passing by horse farms, meandering streams, and the iconic stone fences that define the landscape.

Kentucky is more than just a destination – it’s a cycling experience waiting to be explored. So, grab your bike, breathe in the fresh air, and let the scenic beauty of the bluegrass unfold before you on two wheels. Whether you’re a casual rider or a dedicated cyclist, the Bluegrass Region welcomes you to a world of cycling bliss.

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