To no one’s surprise, most of these events involve drinking or biking. Or both.
March: Urban Iditarod
“Idiots” in costumes are tied to a decorated shopping cart and mush all around downtown, stopping here and there for a drink. Sadly, the Iditarod no longer happens in Portland, but you can travel down to Eugene to watch the idiots every spring!
May: Hero/Villain Power Struggle
At this annual pub crawl, put on by Alter Egos Society, you are welcome to dress up as your favorite hero or villain and go drink with the enemy.
May/June: Bearded Lady Competition
Exactly what it sounds like. Plus vendors, live music and entertainers! Proceeds always go to a different organization and/or charity.
Every summer, bicyclists can choose from hundreds of different biking events, including Drop-Out Prom Ride. If you didn’t get the chance to attend your prom, you can make up for it by dressing in your best prom attire and going out on the town to cycle. You just might get awarded king or queen.
June: Naked Bike Ride
Part of Pedalpalooza, Portland’s Naked Bike Ride is world famous, dedicated to protesting oil dependency and oil transport. Thousands of bikers, wearing underwear and body paint at the most, join together to cycle all around Portland as spectators cheer them on.
This festival brings in quiet and soft music from musicians all around the country to simply sit comfortably and listen to. Yes, sleeping is allowed—and actually encouraged.
August: PDX Adult Soapbox Derby
At the end of the summer, adults meet at Mount Tabor to race down the hills with their homemade soapboxes, each with its own decorations and theme. The Portland community is encouraged to come watch the races and have a picnic and a glass of wine.
Dress up like good ol’ St. Nick and join hundreds of other Santas in a pub crawl! Don’t worry if you can’t make it to the crawl in December—a summer SantaCon happens every July, too.
Every Sunday: Zoobombers
Grab your little brother’s wheels and join other adults with kid’s bikes to race down the West Hills by the Oregon Zoo.
Every day: Portland
Different weird events are happening every day in Portland, though they may not be specifically listed anywhere. Expect the weird, like seeing hundreds of dildos hanging from power lines around the city. Do the weird, like working out at the Green Microgym that uses generated electricity from the exercise equipment to stay lit. And embrace the weird, like supporting your local vegan strip club.