The Essential Portland Bike Events All Year Long
Portland loves a two-wheeled swarm.
It’s True: Portland’s cycling stats took a hit in recent years. But those numbers are creeping back up, and our city’s culture of bike fun—whose roots are deeper than you might think—can still be evidenced in an astounding calendar of bike rides, from the famous World Naked Bike Ride to that one that shuts down the bridges (it’s called the Providence Bridge Pedal). Whether you want to pedal leisurely with friends or slay an endurance ride, these are the essential events—annual rides, then series—on two wheels around town. Not all 2025 dates had been set at the time of publication, and check ride websites for updates before setting out.
Not sated? Consult Shift’s open-source calendar for even more local bike events.
Annual Rides
Worst Day of the Year Ride
February/March
This ride, known for its costumes and its emphasis on fun over speed, perfectly represents the Portland ethos of not letting rain or cold get in the way of a good time. After celebrating its 20th year in 2024, the ride took 2025 off, but we’ll be watching for its return in 2026.
Ladd’s 500
Sat, Apr 12 | Ladd Circle
Reach the Beach
Sat, May 17 | Various Start Locations
This American Lung Association fundraiser starts in the metro area and ends at the coast. Past events have cruised through wine country and ended at Cape Kiwanda; the 2025 ride runs from Sauvie Island to Fort Stevens State Park, with different starting-point options for those not feeling up to 105 miles. Riders can register individually or as a team, and there’s a $200-per-person fundraising minimum.
Pedalpalooza is a summer-long festival devoted to fun on bikes.
Pedalpalooza Kickoff
June (Date and start Location TBD)
2025 is Pedalpalooza‘s fifth year as a three-month event, so expect hundreds of themed rides rolling through this city’s streets all summer long. A huge, all-ages group ride kicks off the fest; the route varies each year, but it typically starts and ends at city parks. Thousands show up, many on their weirdest rigs (tall bikes, tandem bikes, mini bikes) and in their most festive gear. It is, in a word, a scene.
Black Liberation Ride
Thu, Jun 19 | Irving Park
Exclusively for Black and other people of color, this all-ages, no-drop ride, which began in 2015, is meant for Black cyclists to take up space on the streets, gather in community, and celebrate. This year’s ride, which starts and ends at Irving Park, takes place on Juneteenth, the holiday marking the end of slavery in the United States.
Bike Prom
July (Date and Start Location TBD)
Dead Baby Bike Club, whose members identify as advocates of “tomfoolery” and “shenanigans,” hosts this event, which involves dressing up in finery (whatever that means to you), riding around town, and finishing with an epic after-party. Said after-party may include a dance party with live DJs, food and drink, trampolines, and/or lube wrestling in a kiddie pool. Take note: Bystanders get splashed.
Bike Play
July 10–13 & 17–19 (Start Location TBD)
For 15 years, the Working Theatre Collective has written and performed a play that unfolds over the course of a bike ride, complete with original music and choreographed dance numbers. The audience (that’s you) pedals from scene to scene. The 2023 show, Jurassic Bike, started with the premise of Jurassic Park and took a left turn involving bike DNA. In 2024, it was an ode to Hasbro’s Life board game. It’s a gleeful, honestly heartwarming affair.
Seattle to Portland
Sat & Sun, July 12 & 13 | Starts at University of Washington
Why fly or drive or take Amtrak between Seattle and Portland when you can bike? Thousands of riders show up for the one- or two-day, 206-mile ride with plenty of support stations along the way. (This year, it’s July 12–13.) At the end, riders pick up beer garden beverages and lifetime bragging rights. The registration fee—$250 for those who aren’t Cascade Bicycle Club members, jumping to $300 on June 1—includes baggage transport.
Go as bare as you dare on the World Naked Bike Ride.
World Naked Bike Ride
Sat, July 26 (Start Location TBD)
This isn’t just an essential Portland bike ride, but an essential Portland experience, with thousands of cyclists showing up for what is both a protest against oil dependence and a celebration of bodies, with a dance party at the end. There are similar events in other cities around the world, and even other nude-friendly Pedalpalooza rides, including a rival event that spun off in 2024 when this ride took a hiatus. But the OG is back for 2025, so get your body paint ready.
It’s a family affair during the Providence Bridge Pedal.
Providence Bridge Pedal
Sun, Aug 10 | Most routes start at SW Naito Parkway and Morrison
You know that ride that shuts down every bridge in Portland? This is it. Around 10,000 cyclists show up to pedal 20 miles over seven bridges. A 13-mile family ride is also available. Tickets for the main ride are $40 for adults, $30 for youth.
Ride the Rim
Sept 6 & 13 | Crater Lake
This one happens quite a haul from Portland, in Oregon’s one and only national park. For two Saturdays (Sept 6 & 13 in 2025), most of the main road around Crater Lake—the country’s deepest lake—is closed to cars, leaving it clear for cyclists, pedestrians, and runners. The event is free (aside from national park admission), but participants are asked to register so organizers can properly staff and stock aid stations, and there’s a $10 suggested donation.
SERIES
At Sunday Parkways, streets are for people.
Sunday Parkways
May–September | Various Locations
This city-sponsored ride series focuses on one quadrant or neighborhood at a time, closing streets to cars to create a route that’s extra-friendly to beginning riders and families. A few parks along each route host food carts, vendors, bike repair stations, giveaways, and the occasional bounce house. In 2025, things kick off in Southwest Portland on May 18, then continue in Cully on June 29, East Portland on July 27, and finish downtown on September 14.
Portland Trophy Cup
Tue, Sept 9–Oct 14 | Portland International Raceway
Portland adores the raucous sport of cyclo-cross, where cyclists ride through muddy puddles, jump over wooden barriers, and nearly tip over on tight turns. (Yes, you can be terrible at all of these things and still do it.) While many races happen in more remote locations, this six-week series takes place at Portland International Raceway and runs Tuesday evenings in September and October. It’s just as fun to watch as it is to participate, and friendly heckling is encouraged.
Midnight Mystery Ride
Midnight every second Friday | Start Location Varies
Calling all night owls: A Portland tradition for more than 20 years, this ride follows a different route, known only to the ride leader, departing at midnight every second Friday of the month, year-round. The start location, usually a dive bar, is announced day of. Has been known to end with a bonfire.
Breakfast on the Bridges
7–9am every last friday | Various locations
Since 2002, volunteers have served up free coffee and pastries to cyclists (and pedestrians, skateboarders, and anyone else using nonmotorized transit) crossing Portland’s bridges. They currently post up at the Steel and Blumenauer bridges, Tillikum Crossing, and Ned Flanders Crossing (that’s the bike/ped bridge in Northwest Portland over I-405).
Share this content:
Author: Hey PDX
Hey PDX Team
Post Comment