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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.)
And while karaoke is great, drummers and strummers at heart will love Rock Band Karaoke at Ground Kontrol. This regular gathering of Rock Band video game players offers an astounding selection of more than 3,500 songs, along with professional-level lighting and sound systems. Organized like classic karaoke, musicians can take the stage to be background performers on any song (any level of experience is welcome).
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.
December
Stumptown Santacon
Every year in December, Santa Claus comes to town. A mob of Santas. The annual Stumptown Santacon takes over Portland with hundreds of jolly St. Nicks making the rounds to local bars, spreading holiday cheer over holiday beers.
Upcoming Weird Events
Get a taste of the unusual at these strange festivities in Portland.
Benson Hotel Annual Gingerbread Display
The Benson Portland Curio Collection by Hilton invites the public back once again for a live unveiling of the 2023 Gingerbread Masterpiece, a 52-year beloved holiday tradition. The architectural feat promises only one hint to this year’s theme: “A famous example of romanticism, this beautiful sight inspired one dreamer and creator to capture the imaginations…
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…
Low Bar Chorale
You show up at a bar or music venue. You grab a drink, and within minutes you’re singing the hell out of your favorite rock song with a hundred other folks and – wait for it – a live band of nationally known musicians. In three-part harmony, no less. Wait, what just happened? Welcome to…
The Great Figgy Pudding Caroling Competition
Pioneer Courthouse Square is excited to host the Great Figgy Pudding Caroling Competition — a fun, festive, and joyful competition bringing caroling groups to Portland’s Living Room and extending to a ten-block radius downtown. The top three caroling groups will hold a “carol-off” at the Square hosted by KGW’s Drew Carney, and the grand prize…
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 BELLE SUPPER CLUB: A Burlesque Dinner Cabaret
Remember… what goes on AFTER HOURS at the VICTORIAN MANSION stays at the VICTORIAN MANSION. Escape the everyday and delve into cabaret dreams at THE BELLE SUPPER CLUB (located inside the enclosed and heated garden space) while enjoying dinner, cocktails, and delightfully dishy entertainment within the historic art nouveau surroundings of The Victorian Belle Mansion….
Burlynomicon – A Darkly Decadent Burlesque Revue
Burlynomicon – A Darkly Decadent Burlesque Revue invites you to another ghoulishly glorious evening.. the last of it's kind for the dreary year of 2023… filled with eerie and spectral holiday performance at The Coffin Club. Enter into this lush, decadent, and special speakeasy soiree through a hushed bar. You'll descend the staircase to be…
Snow Bar Chorale
Low Bar Chorale presents Snow Bar Chorale. For the 8th annual holiday singalong, with two wild nights of singing, stories, special guests, and the occasional music trivia nerdout. Ben Landsverk and the live band supergroup will lead you through holiday-related alt/indie rock and pop music in glorious 3-part harmony. You’ll get to sing songs by…
Tuba Christmas Concert
Welcome you back downtown for this holiday tradition. Experience the sounds of big brass as over 200 tubas play in unison for the 32nd Annual Tuba Christmas Concert in Portland’s Living Room. Attending this seasonal performance is FREE for the public.
A Burly Carol
Warm yourself from winter's chill with the most sexy of holiday ghost tales that ever was told as Lacy Productions and The Alberta Rose Theater presents… A Burly Carol: A Burlesque Tale Inspired by "A Christmas Carol". Advance discounted tickets are now AVAILABLE. Purchase today. Lacy Productions SELL OUT early. Don't be a humbug… get…
FAN EXPO Portland
FAN EXPO Portland (formerly Wizard World Portland) is the ultimate place to celebrate fandom. Join tens of thousands of fans just like you and experience the ultimate playground for comics, sci-fi, horror, anime, and gaming. Three days of citywide events, family-friendly attractions and world-renowned celebrities await. Attendees can shop at hundreds of vendors and exhibitors,…
Portland Metro Reptile Expo
Northwest Reptile Expos is the largest reptile expo in the Northwest and the longest-running reptile show in Oregon. Come and see the largest selection of reptile vendors in the Pacific Northwest. Northwest Reptile Expos is the only captive-bred reptile show in America. The shows feature a venomous reptile display, an educational display, free raffles and…
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.
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