Best Road Cycling Events in the Midwest in 2022

The team at Strambecco rates the top road cycling events in the Midwest for 2022 based on a variety of 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,   Midwest terrain features of Strambecco’s best list are generally flat or rolling, but routes often include steep short climbs with 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 recommend the GFNY Ann Arbor in June or the Cherry Roubaix Gran Fondo in July.     We also find a strong correlation between the best events and professional event producers.  In the Midwest premiere event producers include Lifetime Events, UCI Gravel World Series, Monuments of Cycling, and 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 contact us here or send us a note at

Best Gravel Cycling Events in the Midwest in 2022

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Individual Events Listings

GFNY Ann Arbor
Location: Ann Arbor, MI
Organizer: GFNY Worldwide Event Series
Date: June 12 @ 8:00 am
GFNY Ann Arbor is one of 25 GFNY Global Event Series  culminating in the GFNY Championship every May in NYC.  Picked as one of our best road cycling events  in […]

RAGBRAI (Ride Across Iowa)
Location: Sergeant Bluff, IA
Organizer: Ventures Endurance Events
Date: July 24 @ 8:00 am
The Register’s Annual Great Bicycle Ride Across Iowa, or RAGBRAI, is an eight-day ride across the state.   Coming on its 50th year RAGBRAI is a classic cycling experience and bucket […]

Cherry Roubaix Gran Fondo
Location: Traverse City, Michigan
Date: July 31
The Cherry Gran Fondo will be back in 2021. Chosen as one of our best road cycling events  in the Midwest, the Cherry Fondo is a hugely popular cycling event […]

GFNY Rockford
Location: Rockford, IL
Organizer: GFNY Worldwide Event Series
Date: August 7 @ 8:00 am
GFNY World Events presents GFNY Rockford, a race in Illinois second largest city, Rockford, located one hour away from Chicago. Chosen as one of our best road cycling events  in […]

Horribly Hilly Hundreds
Location: Blue Mounds, Wisconsin
Organizer: Race Day Events
Date: August 27
Do you want to suffer? If you do then making a trip out to the Midwest’s premiere sufferfest is worth putting on the seasons bucket list. Chosen as one of […]

North Shore Century
Location: Evanston, Illinois
Date: September 18
2022 will mark the 37th annual North Shore Century, one of the Chicago regions most popular cycling events. Chosen as one of our best road cycling events  in the Midwest, […]

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