All participating rides are fundraisers for the sponsoring organizations. Each event features multiple route distances, making the events suitable for a wide variety of riders.


Presented by London Downtown, London, KY. The first event of the 2020 Kentucky Cycling Challenge is the Redbud Ride. The Redbud Ride starts in beautiful downtown London, KY, and stretches throughout the surrounding areas. The Redbud Ride attracts about 800 cyclists from across the country. The routes for the Redbud Ride pass through some of the most beautiful scenery in Kentucky. The routes are filled with blooming Redbud and Dogwood trees! This ride is a must-do for cycling enthusiasts. Our rest-stops are always a party, thanks to our wonderful volunteers and host locations! The Redbud Ride offers five route options ranging from an almost flat 23 miles to the challenging 100-mile route. Our 100-mile route was chosen by as “The Best Century Ride in America.” Riders receive a complimentary pancake breakfast, live music after the ride, pre-ride and post-ride parties, a post-ride meal and the always special Redbud Ride t-shirt.  Register Now HERE

April 18,2020


MAY 22-24, 2020

Presented by the Bluegrass Cycling Club and hosted by Georgetown College, Georgetown, KY. The second “leg” of the 2020 Kentucky Cycling Challenge is the Horsey Hundred. The event features a large vendor expo, live music and local food trucks on Friday evening. The rides on Saturday and Sunday feature multiple marked routes, ranging in distance from 26 miles to the signature 100-mile century on Saturday. Both days, riders will be provided with maps, SAG support and lunch after the ride. Last year, the ride had participants from 27 different states, including large groups from Michigan and the Chicago area, as well as a large group from Ontario, Canada.

Register Now HERE


JUNE 27, 2020

Presented by the Cincinnati Cycle Club. Campbell County, Kentucky  It is our inaugural ride that coincides with our club’s 140th anniversary. We offer a century ride as well as a metric century (66mi.), a 42-mile loop and a casual 29-mile route. Enjoy the beauty and challenge of riding the ridge tops and valleys of Northern Kentucky. See for yourself why many cyclists call this area “God’s country”. You will enjoy beautiful valleys and amazing vistas while pedaling along roads with very little traffic. Each route will have rest stops with a local flair, and will quench your thirst and offer foods to energize you throughout the ride. After successfully completing your ride, relax and enjoy a tasty meal and a cold beverage while you reminisce with fellow cyclists about the panoramic views and the lovely roads you have just enjoyed. Register Now HERE


AUGUST 15, 2020

A fundraiser hosted by and benefiting First Priority a non-profit 501(c)3. The ride begins and runs through downtown Middlesboro before journeying to the back-roads of the beautiful and scenic hills and hollows of Eastern KY with minimal traffic. A lot of our roads wind beside creeks lined with trees offering shade along the way. Rock the Crater has five different routes to accommodate everyone from a beginner to an avid cyclist with distances of 10-mile, 21-mile, 38-mile, a metric century and a full century. All of our routes with the exception of the 10-mile will run through part of the Historical Cumberland Gap National Park. You will not want to miss the opportunity to come visit us and ride RTC. The Tri-State area of Tennessee, Kentucky, Virginia is a great place to visit. It is rich in history, sightseeing, hiking, cycling, and some of the best views you will ever see.  Register Now HERE


Presented by Limestone Cycling Tour, Inc., Maysville, KY. The Limestone Cycling Tour will be the final ride in the lineup which will mark their 12th year for this annual charity ride. In 2019, organizers set a new record, registering over 600 cyclists from 21 states. Participants will enjoy the beautiful rolling hills surrounding Maysville, Mason County and many other communities in the area on the little-traveled back roads. Four routes are offered including a challenging century, metric century, the 40-mile and 25-mile loops. Routes are fully supported with fun themes at many of the rest stops staffed by friendly volunteers. After a fun and challenging day on the road, cyclists can expect to listen to some local music talent or take advantage of special offers at a few local eateries. Recommended by many as a great century and metric route not to be missed! Register Now HERE

SEPTEMBER 12, 2020