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.
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…
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. Bringing you the best in local and international darkly decadent entertainment among the spirits of the eve… Enter this lush, decadent, and special speakeasy soiree through a hushed bar. You'll descend the staircase…
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.
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.
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…
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.
Pedalpalooza
Portland's cycling culture peaks during summer's multi-week Pedalpalooza, featuring 200+ local-led, themed rides, all open to the public.
Star Trek Ride
It's time to take the helm and shift gears to Warp 9. Explore strange new roads and seek out new pit stops and new destinations. Along the way, expect trivia, music, costumes, and prizes.
The Belle Supper Club: A Burlesque Dinner Cabaret
Join Portland's most charmingly titillating vintage dinner experience in the city at The Belle Supper Club. 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…
GeekCraft Expo
GeekCraft Expo is a curated craft market specializing in handmade, “geek”-themed crafts of all kinds; clothing, accessories, toys, home decoration, furniture, art . . . if it’s geeky and made by hand, it can be found at a GeekCraft Expo. Cosplay is highly encouraged and admission is free (you just need to pre-register).
Magical Fantasy & Fae Bike Ride
Did you read all of the Sarah J Mass universe and want to be Feyre Archeron or Manon Blackbeak for a day? Do you get through your work day to really thrive in your DnD campaign? Want to be a wizard like Harry or Gandalf? Planning on moving to the rolling hills of the shire…
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…
Last Thursday
Last Thursday is a community-grown event, free for all artists and art vendors, musicians, performers and visitors. Alberta Street is closed to traffic for the Last Thursdays in June, July and August. On Last Thursday, galleries hold opening parties, and performance venues and bars often host live music and performances. If the weather is nice…
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.
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,…
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…
Portlandia Mermaid Parade & Festival
The Portlandia Mermaid Parade is an eight-year Portland summer tradition. Fun, FREE, and for all ages. Grab your shells and tails and swish your way down to the Portland Waterfront to meet hundreds of other merfolk. There will be an opening ceremony, with performances and the crowning of the Junior mer-ambassadors and Ocean Royalty. The…
Portland Adult Soapbox Derby
The PDX Adult Soapbox Derby at Mt. Tabor Park pits grown-up kids against each other every August in pursuit of speed and laughs.
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…
Geek Week PDX
The Worlds First City Wide Comic Con. The Geeks of Portland are uniting to bring you the worlds largest Pop Culture festival. Fantasy, Sci-Fi, Super Heroes and the Supernatural. Each quadrant of the city will be transformed into a new mythical realm. Cosplay, Film Festivals, Markets, Parties and Tournaments.
The Bloody Mary Festival
The brunch-time party of the year returns for year #5. Don't miss PDX's best Bloody Marys and more – all under one roof – for one day only. TICKETS INCLUDE Portland's BEST Bloody Marys, Cocktail, spirits, coffee, food, and beverage tastes from local companies, One vote for The People's Choice Award, Temp tattoos, photo ops and…
Portland Retro Gaming Expo
This annual celebration of classic video and arcade games features expert panels, cosplay competitions, dozens of local and international exhibitors with rare finds, and a 30,000-square-foot “retrocade” with hundreds of games to play.
Portland Oddities and Curiosities Expo
For lovers of the strange, unusual and bizarre… The Oddities and Curiosities Expo showcases hand-selected vendors, dealers, artists and small businesses from all over the country with all things weird. You’ll find items such as taxidermy, preserved specimens, original artwork, horror/Halloween-inspired pieces, antiques, handcrafted oddities, quack medical devices, creepy clothing, odd jewelry, animal skulls/bones, funeral…
Glass Cannon Live!
Your favorite nerds are back for another year of Glass Cannon Live! Join Troy, Joe, Skid, Matthew, Sydney and Kate as they bring their unique brand of absurdist comedy and epic storytelling. Every show is its own unique live gaming session and you never know what's going to happen until you see it play out…
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.
Kumoricon
Kumoricon showcases anime and Japanese culture every November in Portland. Gaining its namesake (kumori) from the Japanese word "cloudy," Kumoricon embodies the best parts of fandom and what it is to live in the Pacific Northwest. Stretching across generations, anime fans have gathered together for an amazing annual event. The Kumoricon family grows yearly, making…
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