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Best Road Cycling Events Midwest 2024

Best Road Cycling Events Midwest 2024

The team at Strambecco rates the Best Road Cycling Events Midwest 2024 based on various factors, including reputation, route quality, location, rider feedback, and the overall uniqueness of the event or race.  Spanning Michigan, Wisconsin, Illinois, Kansas, Iowa, South/North Dakota, Nebraska, Indiana, and Minnesota, the Midwest terrain features of Strambecco’s best list is generally flat or rolling. Still, routes often include steep, short climbs with a significant elevation gain over the full event route.

If we had to pick the best of the best road cycling events Midwest 2024, or those you’d classify as bucket list events, we’d start with the 8-day ride across Iowa, Ragbrai. We’d recommend the GFNY Ann Arbor in June or the Cherry Roubaix Gran Fondo for single-day events in July.  We also strongly correlate the best events and professional event producers.  In the Midwest, premiere event producers include Lifetime Events,  Monuments of Cycling, Ventures Endurance Events, and the GFNY Event Series.

Strambecco does not list every event.  We strive to identify and review events that are special and noteworthy.  If you have suggestions on other events we should consider or review, please get in touch with us here or send us a note at  Strambecco also rates the Midwest’s best Gravel and MTB events.

Horribly Hilly Hundreds

Do you want to suffer? If you do, making a trip to the Midwest’s premiere sufferfest is worth putting on the season’s bucket list. The Horribly Hilly Hundreds is chosen as one…

ragbrai (ride across iowa) logo

RAGBRAI (Ride Across Iowa)

The RAGBRAI (Ride Across Iowa), is Register's Annual Great Bicycle Ride Across Iowa, an eight-day ride across the state. Coming on its 50th year ("L"), RAGBRAI is a classic cycling experience and…
cyclists at gfny rockford

GFNY Rockford

GFNY World Events presents GFNY Rockford, a race in Illinois' second largest city, Rockford, located one hour from Chicago. Chosen as one of our best road cycling events in the Midwest, this…
road cyclists outside of evanston

North Shore Century

In mid-September, the streets of Evanston and its surrounding areas come alive with the rhythmic hum of bicycle tires at the North Shore Century, one of the Chicago region's most popular cycling…
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