With its vast and varied landscapes, South Dakota offers an unparalleled setting for cycling enthusiasts. From the rugged beauty of the Black Hills to the sprawling prairies, the state hosts a series of cycling events that challenge participants and showcase the state's natural splendor. Among these, the Ride Across South Dakota (RASDak), Dakota Five-O, and Pine Island Gravel Odyssey are premier events attracting cyclists nationwide.  Strambecco rates the Best South Dakota Cycling Events 2025 based on various factors, including reputation, route quality, location, rider feedback, and the event's or race's overall uniqueness. Strambecco does not list every event.  We strive to identify and review special and noteworthy events, spanning Road, Gravel, and Mountain Bike events and races.

The RASDak is a comprehensive cycling tour across South Dakota, allowing riders to experience the state's diverse environments over several days. It's not just the physical challenge that draws cyclists but also the camaraderie and the opportunity to explore South Dakota's hidden gems.

The Dakota Five-O, taking place in Spearfish, is an adrenaline-fueled mountain bike race that features 50 miles of challenging terrain, including more than 90% singletrack and over 6500 ft of climbing. The event is well-regarded for its technical complexity and the scenic beauty of its course, making it a must-do for mountain biking aficionados.

Meanwhile, the Pine Island Gravel Odyssey (formerly known as the Gold Rush Gravel Grinder) is South Dakota’s premier gravel event, taking cyclists through the beautiful Black Hills National Forest. With four route options, including the ultra-endurance Lodgepole Voyage spanning 210 miles, this event caters to all levels of cyclists looking for a gravel-grinding adventure.

Ridge Rider Racing organizes the Dakota Five-O and Pine Island Gravel Odyssey, ensuring top-notch organization and a memorable experience for all participants. These events highlight the physical challenges of cycling and bring together a community of cyclists who share a passion for adventure and the great outdoors.

South Dakota's cycling events are more than just races; they celebrate the sport, the natural beauty of the state, and the welcoming spirit of its communities. Whether you're a competitive racer or a cycling enthusiast looking to explore new terrains, South Dakota offers various events catering to every interest and skill level.   If you have suggestions on other events we should consider or review, please contact us here or send us a note at editors@strambecco.com.  Strambecco also rates the Midwest's best Road, Gravel, MTB events, races, and experiences.