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
Every summer since 2002, local cyclists have crammed the calendar with hundreds of bike-related events over multiple weeks. 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).
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.
August
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.
Haunted Shanghai Tunnel Tour
Old Town Pizza & Brewing is built directly above Portland's infamous Shanghai tunnels. The same tunnels that were used to house kidnapped sailors during the early 1900s. Book a tour and explore the rich history of Portland, and the legacy of Old Town.
Karaoke From Hell
The Northwest's original live karaoke band, Karaoke From Hell, has been rocking Portland for over 25 years and counting. The catalog boasts nearly 700 songs for you to sing, covering every genre from show tunes to skate punk. Catch it every Monday at Dante's and every Thursday at The Spare Room.
BeerQuest Haunted Pub Tour
Uncover Portland’s dark side on this spine-tingling walking pub tour. In the early 1900s, unsuspecting sailors were often ruthlessly abducted and whisked away through the notorious Shanghai Tunnels. Tour guides will tell you how notorious criminals kidnapped thousands of people and why their ghosts still haunt Portland today. This is Portland’s longest-running ghost tour with…
Weird Portland Pub Tour
Experience the eccentricity of Portland, Oregon and visit one of its quirkiest neighborhoods on this walking pub tour. This tour is a must-do for anyone who wants to immerse themselves in the fascinating history of the city, including stories of UFO sightings, Bigfoot sightings, exploding whales, wacky bike rides, strange locals, hijackings, hipsters, artists, and…
The Dinner Detective Murder Mystery Show
America’s LARGEST interactive comedy murder mystery dinner show is now playing in Portland, Oregon. Solve a hilarious mystery while you feast on a fantastic dinner. Just beware! The culprit is hiding in plain sight somewhere in the room, and you may find yourself as a Prime Suspect before you know it.
The Tarot Show
Join Kate Mura as she reads the cards for the audience. Every Group Tarot is different, as every group and every tarot reading is a unique constellation. Stories, anecdotes, conversation, philosophy, questions, history, herstory and ourstory come out specifically for your audience, your day and time, your season. By picking cards, conversing, asking questions, and actively,…
The Original Goat Yoga Experience
Part yoga, part animal-assisted therapy. Goat Yoga is about disconnecting from day-to-day stress and depression and focusing on happy vibes. Beginner-level yoga class taught with the company of our goats. 30 minutes of yoga followed by Goat Happy Hour, free time with our goats to take pictures and enjoy goat cuddles. Our class is held…
A Vintage Vaudeville Variety Extravaganza
Experience a true vintage style variety show . . . right before your eyes: dancers, singers, music, variety acts, and MAGIC. Join the West Linn Historical Society in collaboration with the Oswego Heritage Council as they present their first-ever variety show. Bringing vaudeville back to life at the stunning historic 1920s-era Oswego Heritage House in Lake…
Burlynomicon – A Darkly Decadent Burlesque Revue
Burlynomicon – A Darkly Decadent Burlesque Revue beckons you back into the cozy crypt at The Coffin Club for another delightful soiree. Celebrate another revolution around the sun of producer and host Natasha Riot, as well as bringing you all the gloriously ghoulish entertainment one birthday evening can hold. Enter this lush, decadent, and special…
UFO Festival
Every May, thousands of visitors flock to the city’s famous UFO Festival, featuring four days of parades, costume contests and expert speakers.
Rose Festival Royal Rosarians Milk Carton Boat Race
A classic Rose Festival event and family-friendly community tradition dating back to 1973, the Milk Carton Boat Race is a spectacle you won’t want to miss. Children and adults race and show off their handmade, human-powered boats that float only employing recycled milk cartons and jugs. Creatively constructed watercraft will compete in nine categories, with…
Oregon Bigfoot Festival and Beyond
Join a celebration of Bigfoot, UFOS and Ghosts in a family-fun atmosphere. Celebrities David Schrader of Discovery + The Holzer Files and Ronny LeBlanc of Expedition Bigfoot along with Sarah Lemos of Ghosts Town Terror will be there.
LeakyCon
Inspired by The Leaky Cauldron, the intersection between the magical and mundane worlds, LeakyCon brings together the biggest fans, creators, actors, and artists from the world’s most popular magical franchises. Since 2009, LeakyCon has been a community-focused fan event that provides opportunities to both take joy in the series that we love and critique their…
WasabiCon PDX
WasabiCon PDX is a consumer focused media event designed to connect fans together in a fun, friendly, and entertaining environment. Started in Portland in 2012 under the name Newcon PDX, WasabiCon PDX is one of the PNW’s most popular anime conventions. The event focuses on five key facets of fandom: Anime (including Manga & Asian…
Rose City Comic Con
Portland’s premier pop culture event, Rose City Comic Con, is produced locally with a weird and wonderful vibe unique to the Pacific Northwest. Now in its twelfth year, the ultimate goal remains the same — to deliver the most rewarding, memorable, laughter-inducing weekend ever. While comic books and their mega-talented creators remain the cornerstone of…
Pumpkins and Pints
Pacific Giant Vegetable Growers' TERMINATOR WEIGH-OFF and New Seasons Market Giant Tomato Weigh-Off Watch as the biggest of the big pumpkins and other vegetables compete to win cash prizes. Do you have a giant vegetable that you would like to enter into the Terminator Weigh-Off? Contact Jim Sherwood at fishroadfarm@canby.com from the Pacific Giant Vegetable Growers for information on entering your giant…
West Coast Giant Pumpkin Regatta
This annual race series consists of paddlers piloting a gaggle of gigantic gourds through a watercourse.
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