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 2026 ride runs from Scappoose to Fort Stevens State Park, with different starting-point options in Vernonia, Jewell, and Olney for those not feeling up to 100 miles. Riders can register individually or as a team, and there’s a $200-per-person fundraising minimum.

2026 is Pedalpalooza's sixth 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.

For 16 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; 2025's show was Up Shift Creek. It’s a gleeful, honestly heartwarming affair.

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.

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) and riding around town, plus an epic after-party that 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.

Why fly or drive or take Amtrak or the bus 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 11 & 12.) At the end, riders pick up beer garden beverages and lifetime bragging rights. The registration fee—$275 for those who aren't Cascade Bicycle Club members, jumping to $355 on June 1—includes baggage transport.

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 other nude-friendly Pedalpalooza rides, including an event that spun off in 2024 when the OG, which dates to 2004, took a hiatus. (The spinoff, which calls itself World Naked Bike Ride Portland, goes down this year on Saturday, August 8.) Stock up on that body paint now.

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 $45 for adults, $35 for youth.

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 2026, things kick off in Southwest Portland on May 17, then continue in East Portland on June 28, North Portland on August 2, and finish downtown on September 13.

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.

Billing itself as a “rolling dive bar,”  Thursday Night Ride has been at it since 2015. The ride is not a loop, and routes and ride leaders change weekly, but expect park and store stops and a social pace.

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, often near a dive bar, is announced week of. Has been known to end with a bonfire.

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, Tilikum Crossing, and Ned Flanders Crossing (that’s the bike/ped bridge in Northwest Portland over I-405).