What follows is one of the many articles in the Mercury‘s 2026 Transportation issue. Find a print copy here, subscribe to get a copy mailed to you here, and if you’re feeling generous and want to keep these types of articles coming, support us here.—eds.
Even the most casual cyclist has, at some point, felt the passing desire to race.
Fortunately for these speedsters, Portland and the surrounding area host a variety of different racing events for every type of cyclist—from beginner-focused and inclusive, to fast and competitive, to offbeat and quirky. Your first race is a short ride away.
While Portland cycling breathes with the city’s DIY spirit, official races are governed by the Oregon Bicycle Racing Association (OBRA). OBRA is a member organization, with each bicycle racer contributing either yearly dues or a per-race fee. In exchange, the organization provides a robust calendar of events and resources to help ensure safety and fairness during the races.
OBRA Executive Director Chuck Kenlan told the Mercury the organization works “really hard to make [their] races a place that anybody could feel welcome,” working with promoters and racers to create an inclusive environment.
“It’s good, fair competition, but at the end of the day our races are grassroots,” Kenlan said. “In the end, this is a recreational outlet for folks to have fun and train, to stay fit, and improve their lives.”
Portland is home to a host of OBRA competitions throughout the racing season, which generally kicks into high gear in April and winds down in October. OBRA’s races include lengthy high speed road races, mountain biking, gravel biking, and cyclocross. The Mt. Tabor Series Bike Race is a weekly road racing circuit that runs through Portland’s iconic volcanic park every Wednesday in June and July. Another hotspot in the summer is the Portland International Raceway (PIR), whose track is available for road races, cyclocross, and even adaptive cycling races (overseen by Adaptive Sports Northwest). One late summer-early fall classic at PIR is the Portland Trophy Cup, a six week cyclocross racing series that takes place every Tuesday in September and October.
Ira Ryan, Portland Trophy Cup promoter and course designer, described the Portland Trophy Cup as “part party, part community art project, and part [cyclecross] bike race.” The unconventional ethos of the event extends to the terrain cyclists ride on—
“a little bit on grass, a little bit on pavement, a little bit on gravel, it can be dirt, [or] mud if it’s raining,” Ryan said.
Ryan said some people bring their expensive racing bikes to the Portland Trophy Cup. But others show up on commuters or even beach cruisers. The range of riders—and the race’s short circuit format—make the events especially fun for spectators.
“We want it to feel fun and inviting,” Ryan said.
The Portland Trophy Cup organizers clearly take efforts to include young, diverse, and first-time racers, with youth cyclists and first-time women racers (trans-inclusive) participating for free.
“I love the elite open finishes… going full-speed, full-gas at every corner in complete darkness at the end of the night. [But] the most chills I feel are during the finishes in the beginner women category races,” Ryan said. “When somebody new to the sport is finishing [the race], the enthusiasm is electric. It’s like we’re doing this thing that’s kind of scary, but we’re all doing it together. That’s how you grow the sport.”
Then there’s the Portland Criterium, which embraces competition and intensity. After several years without any criterium (or “crit”) events in the city, the Portland Criterium brought high-octane races back to downtown Portland in 2022. The crit returned last year, with events at the Northwest Portland Park Blocks and the Lloyd Center, where the races will be held again this August. During criterium races, elite racers zip through city streets at speeds upward of 40 miles per hour. The intensity and short tracks make crits very appealing to spectators, who showed up in droves to watch the races last year.
From the sidelines, the Portland Crit is a blur of racing jerseys and a collective buzz of bike chains whizzing past. Inside the peloton, it’s white knuckle competition with no racer wanting to hit the brakes even for a half-second. Adding to the intensity is the near-guarantee of high-speed crashes and road rash. Crits are a type of race a mountain bike-racing friend of mine once called “completely psycho” (complimentary). After the success of the past few years of the Portland Criterium, OBRA announced that the 2026 race at the Lloyd Center will double as the Oregon State Criterium Championship.
“Think of the Criterium like the bicycle equivalent of Formula 1,” Portland Criterium race director Steven Beardsley said. “[Racers] ride on real city streets, they come around [the short track] about every minute, and ride at full speed for the entire race.”
Beyond the bicycle race itself, Beardsley also pointed to the Criterium’s effect on the city streets it takes place on.
“Coming out of the pandemic, the Criterium was a way to help activate parts of Portland that maybe haven’t gotten as much excitement,” Beardsley said. “But it also can transform our auto-centric streets into something cool for a weekend, a fun event with bike racing, DJs, and just tons of community spirit. Bike culture can feel a bit siloed at times, but this is a real event for the public.”
Portland’s bike racing scene goes into some more niche and chaotic areas, too—from the Sandy Smash bicycle drag race on the city’s most infamous diagonal throughway, to the fixed-gear alleycats that take place throughout the year. You could also stumble upon summer sprints on North Williams. And does the Ladds 500 count as a race? (No, it’s a relay.) Whatever your vibe, there’s a bicycle race for you here. Get out and find your peloton.
Find out more about OBRA at obra.org. The Shift calendar at shift2bikes.org is a good general resource for Portland’s bike events. For the more indie races, you’ll have to turn to Instagram—check out @pdx__fxd to start.
