From a group of “bike punks” and messengers having a good time in the park 10 years ago, over the years, the Ladds 500 has been adopted into Portland’s roster of annual eclectic events.

For the first four years, the event was an unofficial gathering, but it has since turned into a colorful parade of costumes and bikes that draws hundreds.

The festive relay, which takes place over the course of several hours in the center of the Ladd’s Addition neighborhood in Southeast Portland, has few rules — and that’s by design, according to founder David Barstow Robinson.

“Rule No. 1 is: Don’t be a dick. All of the other rules are basically variations on that theme,” Robinson said. “The goal is not enforcing, the goal is encouragement of being responsible to the greater thing. And that’s—when it works—one of the things that is beautiful about the event.”

While the event is decidedly anti-rule and pro-having-fun, the basic outline is that teams of at least one person must switch riders or equipment at least 10 times.

Teams show up in costumes, riding bikes or other creative machines with wheels, and turn left in a circle for about seven hours or until the 500 laps are completed. Those laps equal about 100 miles — depending on whether the participant is traveling on the inner or outer part of the circle.

As the event has grown over the years, Ladds has attracted more than just the biking community. Rollerskating groups and a few people from the running community have also been known to take up the challenge, while the neighborhood and local businesses have embraced it as an annual event, according to Robinson.

“What I love is the folks every year who will say, ‘My watch said I did 30 miles! I didn’t know I could do that,” Robinson said.

News Source : https://www.opb.org/article/2026/04/12/portlands-silliest-relay-event-returns-for-10th-year/