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Portland’s Weirdest Events
Costumed bike rides? UFO festivals? These events keep Portland weird all year long.
John Patrick Pullen
Portland comes by its eclectic reputation honestly. Sure, we celebrate normal stuff like roses and beer, but we also throw in regular events dedicated to quiet music, strange films and riding bikes while wearing crazy costumes — or nothing at all. From quirky to downright bizarre, here are some of our favorite “Keep Portland Weird” events.
Year-Round Weird Events
Weird Karaoke Nights
In addition to standard karaoke bars, Portland has several unusual singalong offerings: Karaoke from Hell (which happens at multiple bars around Portland, including Dante’s and Spare Room) lets you sing with a live band. In Southeast Portland, Baby Ketten Klub features custom mixes of impossible-to-find songs (and was called “America’s greatest karaoke night” by The New York Times.)
Last Thursdays on Alberta
Closing off 15 blocks of Northeast Alberta Street to cars during summer months, Last Thursday on Alberta has grown fantastically since it started more than 20 years ago. With artists, performers and craftspeople filling the streets and sidewalks, Last Thursday is a great place to get a purely Portland souvenir. And with thousands of people in attendance, it’s also a great place to take in the local flavors.
Weird Events by Month
May
Filmed by Bike Festival
Showing just how bike-crazy Portland is, the Filmed by Bike Festival at Northeast Portland’s historic Hollywood Theatre features bike-themed short movies (each no longer than eight minutes) made by independent filmmakers worldwide.
UFO Festival in McMinnville
Thousands of earthlings flock to McMinnville, a quiet Willamette Valley town located an hour southwest of Portland, every May to attend the city’s famous UFO Festival. Second in popularity only to the UFO festival in Roswell, New Mexico, Oregon’s annual celebration features three full days of parades, costume contests, expert speakers, dance parties, live music and family-friendly fun.
June
Pedalpalooza
Since 2002, local cyclists have crammed the calendar with hundreds of bike-related events over multiple weeks every summer. The Pedalpalooza roster includes everything from Portland’s iconic World Naked Bike Ride (see below) to the Flamingo Ride (where people dress up themselves and their bikes as — you guessed it — flamingos).
July
Portlandia Mermaid Parade & Festival
Honoring Portland’s connection to its rivers, port history, and, of course, mermaids, the Portlandia Mermaid Parade and Festival is a free, annual event celebrating all things aquatic. Held downtown at Tom McCall Waterfront, the event features a colorful parade, delicious food carts, and a chance to immerse yourself in Portland’s quirky and creative merfolk culture.
August
World Naked Bike Ride
Wearing nothing but helmets and smiles (and maybe some body paint and fairy wings), thousands of bicyclists take to Portland streets every summer to protest oil dependency. Portland’s edition of the World Naked Bike Ride is the largest on the planet, but it’s not as serious as it sounds — the nighttime ride snakes all over the city with crowds cheering on the buck-naked bikers.
PDX Adult Soapbox Derby
Every August since 1997, the PDX Adult Soapbox Derby has seen select teams of grown-up kids piloting homemade soapbox derby cars down Southeast Portland’s Mt. Tabor Park. Vehicles have included miniature A-Team vans, Batmobiles and the always popular Flintstones-mobile. Crowds line the track with picnics and bring-your-own beer and wine, cheering on the daring speedsters.
October
West Coast Giant Pumpkin Regatta
Watch and cheer people on while they paddle gigantic pumpkins across a lake during the West Coast Giant Pumpkin Regatta. Drawing thousands of people each year, this free, wacky annual event is the only one of its kind on the West Coast.
Upcoming Weird Events
Get a taste of the unusual at these strange festivities in Portland.
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