In Portland, being dubbed “weird” is never an insult. Locals delight in enjoying the pleasantly unexpected, whether it be watching adults zoom down an extinct volcano in soapbox derby cars, joining in on one of the world’s largest naked bike rides, or crafting deliciously strange new types of doughnuts. Do as locals do and embrace the city’s quirky vibes using our guide to Portland’s weird culture, then check out our events calendar to find even more unique things to do on your next trip to The Rose City.
If you’re in the mood for doughnuts with peculiar flavor combinations, like, say, one topped with Cap’n Crunch Cereal, then make sure to include a visit to Voodoo Doughnut. With multiple locations across the nation, this Portland shop attracts customers with crowd pleasers such as the Maple Bacon Bar and their more adventurous (and hotter) varieties like the Ring of Fire Doughnut — a Devil’s food cake dusted with cinnamon sugar, cayenne pepper and topped with a whole, dried red chili pepper. Open 24 hours a day, almost every day of the year, Voodoo has one-of-a-kind treats for every taste.
Wyrd Leatherworks and Meadery, set in the basement of a vintage Portland building in the Woodstock neighborhood, is a medieval fantasy-themed mead hall. Made with local honey in their subterranean space, expect to find LARPers and fans of cosplay kicking around this distinctive bar.
With several small bars and a brewery, McMenamins Kennedy School is an unusual place to get an education in hops and barley. Now home to a 57-room hotel, the decommissioned 1915 schoolhouse features a movie theater, and a saltwater soaking pool (they even allow cigar smoking in the “Detention Bar”). And with Portland’s abundance of breweries, there’s no better place to work on your advanced degree in craft beer appreciation.
And if you’re still craving something more daring, you might find it at Sushi Mazi, where they’re serving up grasshopper sushi along with other delicious and unique takes on classic Japanese dishes.
Brew ‘N’ View – Movie Theaters That Serve Beer
Portland’s beloved “brew ‘n’ view” movie theaters run the gamut from funky to swanky, serving up all manner of drinks, food and films.
Rose City Rollers Roller Derby
The all-female, volunteer-run roller derby team battled its way to the top of Portland’s sports fandom, and a world championship, in recent years.
Portland’s “Mystic District”: Three Magical Shops in One City Block
Whether you’re curious about crystals, dreaming of divination decks or just seeking sweet-smelling soap, Portland’s Mystic District has the store for you.
Portland’s Shanghai Tunnels
In the late 1850s, a lonely logger might get more than he bargained for at his local tavern. See Portland's historic underbelly on a Shanghai Tunnel tour.
Portland is rife with spooky lore and tales of things that go bump in the night; find them with these mysterious spots and spirited walking tours.
Weird Outdoor Adventures
Hike your way to the Witch’s Castle in the 5,172-acre Forest Park. As the largest, forested natural area within city limits in the U.S., it is home to more than 100 species of birds and dozens of kinds of mammals. It’s an unparalleled urban wildlife asylum with miles of hiking and biking trails, and epic views of Mt. Hood.
Visit (or walk by) the world’s smallest park on your way to people-watch at the much larger waterfront. Initially planted in 1946 by a writer whose street-facing desk overlooked a hole dug up for a pole that was never installed, Mills Ends Park is now officially maintained by the city. There is lore that leprechauns frequent the area, so many passersby will leave offerings, including tiny swimming pools, statues and a Ferris wheel. You never know what you’ll find at this quirky spot.
Check out an abandoned UFO boat located on a clothing-optional beach in Sauvie Island. The fang-shaped vessel was initially built as an apocalyptic-proof floating bunker able to house twelve people. Now heavily graffitied, the chassis shows the remnants of a once functional kitchen and a small living space. Safety precautions should be taken if entering the structure.
As for hand-built marvels, Stumptown has more than its share. Constructed by skateboarders without the city’s permission, the Burnside Skatepark is a massive cement mecca for the sport located under the Burnside Bridge’s eastern side. Eventually approved by the local government, the rebellious ramps and half-pipes are community-run and packed with skaters — sometimes even pros like Tony Hawk stop by, too.
The atmosphere is much less competitive at Oaks Amusement Park, where the Northwest’s largest roller rink still features music played on a nostalgic old pipe organ. Since its opening in 1905, the park has provided nearly a century of nonstop kid-friendly games, rides, and memories.
And while the renovated Crystal Ballroom is not quite as old, it has an equally remarkable vintage feature: a 90-year-old, mechanical “floating” dance floor that has springs under its surface. The music comes in a bewildering range of styles—folk, jazz, a hundred flavors of indie rock, soul and singer-songwriter. The list of touring bands and locals goes on and on. With its high ceilings, ornate balcony, grand chandeliers, and expansive floor-to-ceiling arched windows, this venue is keeping dancers bouncing around and moving like nowhere else.
If you prefer non-pipe organ music for your roller skating fun, the not-so-secret Secret Roller Disco might be more your scene. This free event happens every Thursday night, rain or shine. Location and times can change depending on the season, so be sure to check their Instagram for the latest. Festive attire is encouraged.
To understand the bumper stickers and Old Town mural calling to “Keep Portland Weird,” look no further than the weird ways that Portlanders celebrate, from the thousands-strong World Naked Bike Ride, the summer-long Pedalpalooza, to the daredevil antics of the Zoobombers and the Portland Adult Soapbox Derby. Not as weird, but no less distinctive, are the beer festivals held nearly every month (and almost every week in the summer), which include celebrations of specific types of beer, like organic, sour, rye, and fruit.
About 40 minutes southwest of Portland, you can find McMinnville’s UFO Festival. The family-friendly UFO Festival includes three days of special events, including live music, expert speaker panels, a colorful parade, a pet alien costume contest, and more.
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…
Stinkfest Queens and Ecotrust present The Annual 2023 Portland Fermentation Festival Come out for the 2023 return of the Portland Fermentation Festival. Joining will be the honorary guest speaker, Kirsten Shockey, co-founder of The Fermentation School and renowned author of several excellent and bestselling fermentation books, including her expert guide, Fermented Vegetables and latest hit,…
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…
This annual race series consists of paddlers piloting a gaggle of gigantic gourds through a watercourse.
The Portland Zine Symposium is an organization that hosts, among other events, a yearly free conference and zine social exploring facets of independent publishing and DIY culture. This event has been held in Portland, Oregon in the summer since 2001 and hosts over 150 tablers from around the world each year, as well as many…
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