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Best Road Cycling Events in the Midwest in 2023

Best Road Cycling Events in the Midwest in 2023

Updated Nov 7, 2023

The team at Strambecco rates the top road cycling events in the Midwest for 2023 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, or those you’d classify as bucket list events, we’d start with the 8-day ride across Iowa, Ragbrai. For single-day events, we’d recommend the GFNY Ann Arbor in June or the Cherry Roubaix Gran Fondo 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

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