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Best Road Cycling Races Midwest 2024

Best Road Cycling Races 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.

ragbrai (ride across iowa) logo

RAGBRAI (Ride Across Iowa) 2024

Updated June 27, 2024 — The RAGBRAI (Ride Across Iowa) is the Register’s Annual Great Bicycle Ride Across Iowa, an eight-day ride across the state. Coming on its 50th year, RAGBRAI is…

Start line of Ride Across Indiana event

Ride Across Indiana – RAIN 2024

Last updated June 27, 2024 — The Ride Across Indiana – RAIN is a premier cycling event that encapsulates the spirit of adventure, endurance, and camaraderie.  Produced by Bloomington Bicycle Club, this…

road cyclists outside of evanston

North Shore Century 2024

Last updated July 10, 2024 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…
Riders with unique South Dakota hills backdrop

Ride Across South Dakota – RASDAK 2025

Last Updated June 10, 2024– The 2025 event date is not confirmed — RASDak, or Ride Across South Dakota 2025, is a captivating event that invites cyclists to explore the diverse landscapes…

Horribly Hilly Hundreds 2025

Updated July 5, 2024 — The 2025 event date is not confirmed — The Horribly Hilly Hundreds 2025 is the Midwest’s premiere sufferfest and is worth putting on your season’s bucket list.…

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