There’s nothing quite like riding a bicycle. The wind in your hair. The sound of your wheels on pavement and gravel. The pace of your breathing in time with each revolution of the pedals. And best of all, the exhilarating sense of speed — especially on the downhills. (Let’s all agree not to talk about the uphills.)

Cycling is a cornerstone of this magazine, and we’re fortunate to have a truly exceptional cycling community in our hometown of St. Louis (see this article from 2020 for a historical account). As we continue to celebrate our 10th anniversary in 2024, we asked local experts and consulted our most recent Readers’ Choice Awards to create a list of 10 Midwest cycling races that rise above the rest. Did we leave out some great Midwest cycling races? Of course. But here are our top picks.

Tour of Hermann Gravel Challenge

Date: May 4-5
Location: Hermann, Mo.

The rolling hills that predominate central Missouri and the gravel roads that serve them are the canvas for this Midwest cycling race. Three routes on Saturday and two more on Sunday provide opportunities for racers of all abilities. Each loop varies in length and is mile-for-mile almost entirely unique, though each begins and ends at Hermann City Park. Along with riverside scenery, participants are in for a treat once they hop off the bike on Saturday night: catered dinner, beer pours, and local wine are all covered by the registration fee.

Unbound Gravel

Date: May 30-June 2
Location: Emporia, Kan.

Founded in 2006 at a time when gravel grinding was just gaining traction, this race now attracts thousands from around the globe to tackle the tire-shredding roads of the Flint Hills. The roughness of the course, as well as the temperamental Midwest weather, can make or break your day. And bring your climbing legs; while the hills aren’t big, they’re persistent. Unbound Gravel kicks off on Thursday with the All Things Gravel Expo. On Friday, the first race starts: 350 miles and completely self-supported. The 200-, 100-, 50-, 25-, and Junior races all begin on Saturday.


Date: July 20-27
Location: Across Iowa

RAGBRAI, short for Register’s Annual Great Bicycle Ride Across Iowa, is the oldest, largest, and longest multi-day bicycle touring event in the world. Drawing pedalers in the tens of thousands, it’s less a “ride” and more a rolling festival of bicycles, music, food, and community. The west-to-east crossing changes routes every year. In 2024, RAGBRAI will veer to Iowa’s rural south and, for the first time ever, will offer daily optional gravel sections from 2 to 14.5 miles in length. Register for a day pass or sign up for the entire 468-mile experience.

Gateway Cup

Date: August 30-September 2
Location: St. Louis, Mo.

St. Louis’ largest competitive cycling event takes place every Labor Day weekend in four historic neighborhoods: Lafayette Square, Francis Park, The Hill, and Benton Park. As you can see below, the city views are outstanding.

Regardless of the location, the criterium-style races consist of multiple laps set on closed city streets, which makes them extraordinarily exciting for riders and watchers alike. There are nine races each day, ranging from newbies to pros. Enjoy food, drinks, vendors, and announcers doing play-by-play via loudspeaker. The weekend also includes recreational rides, runs, and parties for all.

Giro Della Montagna

Date: September 1
Location: St. Louis, Mo.

A casual spin-off of the Gateway Cup, Trailnet hosts its Giro Della Montagna each year on the morning before the same-named bicycle races. This Midwest cycling race complements Trailnet’s rural rides — less forest green and more red brick — and rolls through charming neighborhoods like Carondolet, the Central West End, and, of course, The Hill. (Giro Della Montagna literally means “Tour of The Hill” in Italian.) Four routes from 4 to 50 miles begin and end near where the races take place later in the day, making for a great start to a day of cycling.

Bike MS: Gateway Getaway Ride

Date: September 7-8
Location: Godfrey, Ill.

Held the weekend after Labor Day and benefitting the National Multiple Sclerosis Society, this Midwest cycling race features two full days of riding. The routes (25, 50, 75, and 100 miles) travel along the limestone bluffs on the Great River Road, showcasing majestic views of the Mississippi River and passing through historic areas. The event is known for its first-class volunteer support and rider amenities: bike repair and storage; fully stocked rest stops; meals; shower trailers; nightly entertainment; games; and more.

Moonlight Ramble

Date: September 16
Location: St. Louis, Mo.

In 1964, Dick Leary organized a midnight bicycle ride starting at St. Louis Union Station. No one else showed up, so he rode by himself. He tried again the next year, and a few people joined him. Even more came the following year. Within a decade, the ride was attracting thousands of participants. Live music, vendors, food, and VIP-level amenities have been added over the years, yet nothing has changed the family appeal of the leisurely nighttime ride, a touchstone for generations of area cyclists.

Pedal the Cause

Date: September 21-22
Location: St. Charles, Mo.

Big news for 2024 is that Pedal the Cause will relocate its hub to Family Arena in St. Charles. Saturday will feature a Kids Challenge in the morning and Taste the Cause in the evening. Sunday will include a full day of riding (six road and two gravel options), spinning, and gathering as a community to celebrate 15 years of impact. This particular Midwest cycling race is one of the top 10 largest cause-related cycling events in the country, having donated over $45.8 million since 2010 to fund the best and brightest ideas in cancer research.

Ride the Rivers Century

Date: September 28
Location: St. Charles, Mo.

One of the more unique 100-mile routes in the Midwest, Ride the Rivers Century takes  participants on river ferries, city and country roads, and urban trails past orchards, prairies, small towns, and larger cityscapes. At the end of their journey, riders arrive back at a block party on the Streets of St. Charles, featuring food, drinks, and a well-earned rest. Want to join in on the fun with fewer miles? The Metric Century measures 64 miles (100 kilometers). Ride through many of the same landscapes as the 100-miler and enjoy the same benefits and support.

World Naked Bike Ride

Date: July 27
Location: St. Louis, Mo.

Part spectacle and part social movement, this as-bare-as-you-dare event provides riders an opportunity to ditch the restrictive bike shorts and promote cyclist rights and body positivity — and also to protest against oil dependence. (It’s complicated.) But you don’t have to be an activist, or even nude, to participate in this fun Midwest cycling race. Many people join the free event in their underwear or fanciful costumes The 10-mile ride on city streets happens each year, with as many as 3,000 participants and a raucous after-party in The Grove neighborhood. And we do mean raucous.

Author: Brad Kovach is the founder and publisher of Terrain Magazine.

Top photo: Courtesy Pedal the Cause.