In a city known for its love of bikes and offbeat traditions, Portland may have outdone itself again this weekend.
Hundreds of cyclists descended on the tight, tree-lined streets of Ladd’s Addition in southeast Portland on Saturday for the 10th annual Ladds 500—a tongue-in-cheek endurance challenge that asks teams to circle a single neighborhood traffic circle 500 times.
Yes, 500.
The premise is intentionally absurd. Riders loop endlessly around the small roundabout, trading off laps with teammates, counting revolutions, and embracing the kind of joyful, slightly unhinged energy that has made the event a cult favourite in the city’s cycling scene.
The Ladds 500 (photo: Instagram @tiredlittleman and @ladds500)
Organizers don’t pretend otherwise. Their official rationale for the event’s existence is disarmingly simple: “It’s spring—let’s do something stupid.”
What started as a quirky grassroots gathering has grown into a full-fledged spectacle over the past decade, drawing costumed riders, elaborate team themes, and a steady stream of spectators lining the circle to cheer, heckle, and ring cowbells.
The Ladds 500 is organized by Umbrella, a Portland-based 501(c)(3) that supports what it calls the city’s “most vibrant and scrappy transportation, art, and activist projects.” The event reflects that mission perfectly—equal parts bike culture, performance art, and community gathering.
There are no finish lines in the traditional sense, no prize purses or podium pressure—just the shared goal of hitting 500 laps and surviving the dizzying repetition. And yet, in its own eccentric way, the Ladds 500 captures the essence of cycling culture: the point isn’t distance or speed, but simply showing up, riding your bicycle, and having a very good time doing it.
Please, we need more silly cycling traditions.
(Lead photo: Instagram @tiredlittleman and @Ladds500)