This holiday weekend, world-class bike racing zooms through St. Louis. Elite professionals from around the world compete for glory and prizes, and regular folks and kids can join the fun as well.
The Gateway Cup sends racers through their paces on 1-mile “criterium format” races in Lafayette Square (Friday), Francis Park (Saturday), The Hill (Sunday), and Florissant (Monday). The dramatic format is fun to watch—the pack of cyclists speeds past every few minutes, navigating the route with mere inches between them.
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“I think there are two types of fans,” says event director Mike Weiss, who also owns Big Shark Bicycle Company. “There are people who know there’s a cool bike race and cool neighborhoods, and they get exposed to it for the first time. Then, you have the people who recognize this is one of the top pro events in the United States—it’s rarefied air.”
There are nine races per day, sorted by ability, gender, and age. The final races of each day are the men’s and women’s pro races, and the payouts for the pros are equal for men and women. “The Gateway Cup is the final for two of the biggest professional series in the country,” Weiss explains; there’s the American Criterium Cup, the country’s top pro series, as well as the USA Masters Cup, the top event for cyclists over age 40. “There’s a lot of prestige that comes with that—doing well in this series is a path forward.”
Top finishers can move onto elite teams that compete internationally including in places such as Europe and South America, with much more of an entrenched culture around bicycle racing.

Despite that rarefied air, the events are very accessible. “I’m a huge sports fan. I like to watch, but I also like to do,” Weiss says. “It’s a good blend. People can do something super positive in their own community, and then they can watch the people who do the sport professionally.”
The Gateway Cup has races that are kid-friendly and beginner-friendly, and it features parties, fundraisers, and great ways to visit city neighborhoods. It also makes space for hobbyists to hobnob with cycling greats. “When all of the riders come to town, they want to shake out their legs,” Weiss explains.
On Thursday evening, starting from the Big Bend location of Big Shark, the pro riders will join a fun race that’s open to amateurs and pleasure riders. “That’s like going out to play catch with the Cardinals,” he says.

Even for casual fans of the sport, the party atmosphere is top-notch. Thousands of people visit city neighborhoods (and patronize their businesses), and residents can watch an elite event from their porch. “We don’t have a ticket; I’m not worried about ticket sales,” Weiss says. “Our support comes from the community and local business leaders.”
While watching from the sidelines is a singular experience, there will be other ways to enjoy the event. A former national champion, Daniel “Hollywood” Holloway is embedding with the race, providing livestreaming and commentary from within the racing packs. There will also be cameras in front of the races, on the pace car, and on a low-altitude drone flying above. If you’re looking for a rivalry, watch for Legion of Los Angeles and REIGN Storm, a Louisville team with racers from across the country (including St. Louisan Tim Smith) as well as from Colombia and Mexico.
The event is in its 38th year, and while it’s stayed true to its original hometown ethos, it’s grown a lot under Weiss’ hand the past two decades. “When I took it over, I felt like it had everything but credentials,” he says. “There was no real reason why a team of international riders would want to come to St. Louis or even why they would be aware of the event.” He took on the task of learning and meeting the requirements for the sport’s governing bodies. “The Gateway Cup is now positioned as the final race of the top race series,” he says.