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.


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 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, a 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


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

October 10,2020