Portland is really… REALLY weird. We might have stolen the “keep Portland weird” catchphrase from Austin, Texas but I’d argue that if our Unipiper was leading us into a battle over weirdness, we would undoubtedly win. If you’re headed to Portland and want to get a little weird, here are 56 ways to do it.
56 Fun, Unique, and Unusual Things to do in Portland
#1. Be the big spoon
At Cuddle Up To Me you can enjoy a fully clothed, totally platonic cuddle session with a “master cuddler” for anywhere from 15 minutes to 5 hours. Perfect if you’re craving the physical touch of a complete stranger. Double dog dare you to spoon for 5 hours!
#2. Visit the Clown Room at Funhouse Lounge
The Funhouse Lounge serves up strange nightly shows like Dominatrix Improv or Burlesque Stand-up Comedy that alone would make this a worthy stop on our weird Portland to-do list. But the icing on the cake is their clown room where you can sip a cocktail while surrounded by hundreds of creepy clown pictures. Guaranteed to induce nightmares for any coulrophobiacs out there.
#3. Visit the World’s Smallest Park
At just 452 square inches, Mill Ends Park is the smallest park in the world according to the Guiness Book of World Records. You can find it at the corner of SW Front Avenue and Taylor Street. Be sure to stop by for a photo while wandering around downtown Portland!
#4. Explore the Shanghai Tunnels
Have you ever heard of “shanghaiing”? It’s the illegal capturing and selling of able-bodied men to sea captains and it used to be an underground operation in Portland, Oregon. Literally underground. The Shanghai Tunnels run underneath the city connecting the downtown area to the Willamette River. According to legend, men were drugged (or simply overly intoxicated), kidnapped, dragged into the tunnels, and then held captive until they could be sold.
You can take a tour of the underground tunnels and learn more about Portland’s sordid past.
#5. Buy a joint (don’t worry, it’s legal!)
If you are over the age of 21, the use of recreational marijuana in a private residence is legal in Oregon. And you’ll find plenty of dispensaries all over the city where you can walk in, talk to an expert about strains, and then walk out with a joint. Just don’t tell mom. Oh, and don’t try to take it across the border with you.
#6. Zoom around town on an electric scooter
The electric scooter craze has arrived in Portland and they are now super easy for busy commuters and carefree tourists to rent. Just sign up for the mobile app by one of the 3 companies piloting the technology – Bird, Lime, or Skip Scooters – then locate an available scooter and use your app to start your scooter rental. Off you go!
Zoom zoom fellow weirdos.
#7. Try the Voodoo Doughnut Eating Challenge
Want to win a button and the money you spent on your doughnut back? You just have to do the following, in under 80 seconds:
- Consume an enormous doughnut that weighs .5 lbs and is the equivalent of eating 1/2 dozen smaller doughnuts
- You can drink liquids and/or dunk the doughnut
- The time begins as soon as you touch the doughnut
#8. While you’re there, get married at Voodoo Donut
Cause, why the hell not?
#9. Snap a photo of your feet on the PDX carpet
The PDX carpet gained notoriety due to its unique design and the fact that people loved to take pictures of their stocking feet on it. It was the classic social media sign that you were coming or going. The infamous carpet has been replaced with an updated design but it’s still worth snapping a shot of your toes when you disembark.
Better yet, buy a pair of PDX carpet patterned socks to wear for your PDX carpet sock photo!
#10. Play old school video games at Ground Kontrol
With over 60 classic video games and 27 pinball machines, Ground Kontrol is a gamer’s paradise. Kids have to leave in the evening when the bar opens so that the adults can really let loose!
#11. Eat “bone marrow” ice cream at Salt & Straw
You’ll find countless ice cream shops around Portland boasting unique flavor combinations that mix sweet with salty. But the first one to really step outside of the box was Salt & Straw. And to this day they remain the most popular. If you go on a hot day you’ll undoubtedly have to stand in a line that trails out the door and down the block but trust us, the wait is worth it.
Plus they’ll let you sample as many flavors as you’d like before settling on your favorite!
Pro Tip: Don’t want to wait in the line at Salt & Straw? You can have get a pint delivered to you by Amazon.
#12. Go antiquing at Hippo Hardware
When you see the toga-clad hippos painted on the columns in front, you’ll know you’re at the right place. Hippo Hardware is theoretically a salvage and hardware store. But this behemoth 3-story, 30,000 square foot business also offers “assorted collectibles, trinkets, whatnots, and whoziwhatsits depending on what we get in.”
Not only are you free to rummage through the various assortment of strange knickknacks they have acquired over the years, it’s strongly encouraged. According to their website, “The spirit of Hippo Hardware is to rejoice in the individual, the unique, and the original.” How Portland is that?
#13. Sleep in a Haunted Hotel
The Heathman Hotel has been called one of the most haunted hotels in America. Guests report items mysteriously moving around the room, the sensation of someone crawling into bed with them, cold spots, strange noises, and hazy faces staring out of the shadows. Rooms 703, 803, 1003 are particularly active with paranormal activity.
Stay there… if you dare…
#14. Meet the West Coast’s Oldest Drag Queen
Walter Cole was born in 1930. He had a wife and two children and lived a “conventional” life in Portland before developing his “alter ego” – Darcelle XV. He first wore a woman’s dress at age 37 and is now the oldest female impersonator on the West Coast. You can still see him and other beautiful ladies performing drag burlesque at his popular venue, Darcelle’s XV.
#15. Sing a “stripperoke” karaoke tune at Devil’s Point Strip Club
Portland has the most strip clubs per capita of any city in the US – one for every ~11,200 residents. But most of the strip clubs in Portland aren’t exactly “run of the mill”. You’ll find tattooed women with mohawks cutting the heads off of sex dolls with a chainsaw and all types of other bizarre burlesque behavior. Don’t mess with them, they can definitely kick your ass.
Every Sunday night Devil’s Point hosts “stripperoke”. It’s like karaoke, but with strippers dancing around you while you sing. It’s great fun for the whole family! Just kidding, adults only…
#16. Sing karaoke with a live band at “Karaoke from Hell”
Get the chance to feel like a real rock star by singing karaoke with a live band! Every Monday night Dante’s hosts “Karaoke from Hell” where you can pick from the hundreds of song options, stand on stage in front of a crowd of cheering fans, and jam out with a live band.
#17. Ride naked at the World Naked Bike Ride
Once a year, hundreds of Portlanders strip off their clothes, jump on their cruisers, and join the World Naked Bike Ride and subsequent awkward naked after-party. It’s great fun, just make sure you add extra cushion to your seat so those bare buns don’t chafe.
#18. Rent a hot tub by-the-hour
Portland Tub-and-Tan has a variety of hot tub options for both large and small groups. Open-air rooms offer built-in fireplaces, large-screen tvs, mood lighting, and surround sound. It’s the perfect place to host a Super Bowl party or to take a first date if you want to be super awkward.
#19. Enjoy Japanese food and porn at Tanuki
Tanuki is an eclectic Japanese restaurant in the Montevilla neighborhood of Portland. They are known for their motto – “No sushi. No children.” And for the delicious and creative drinking food that they serve. You’ll need to tell them how much you want to spend and they’ll take care of the rest. While you’re eating you can enjoy whatever strange anime porn or stripper zombie movies are playing on the television screens.
#20. Eat Vegan at the Casa Diablo Strip Club
Does it even get more “Portland” than a vegan strip club? No, no it doesn’t.
#21. Visit the Freakybuttrue Peculiarium
The Freakybuttrue Peculiarium is both a museum and a store and is filled with strange oddities that you never knew existed. You must see them to believe.
#22. Sleep in a Tiny House
Caravan – a Tiny House Hotel is an eclectic hotel made up of 6 custom-built tiny houses arranged around a central courtyard. Not only can you experience what it’s like to live in a tiny house, but they also have nightly bonfires with s’mores and occasional live music!
Read about some other unique boutique hotels in Portland.
#23. Drink coffee while petting cats at a “cat cafe”
Purringtons Cat Lounge is a “cat cafe” and adoption center where you can sip wine while petting adoptable cats. If you’re in the market for adoption, or just want to hang out with cats for the afternoon, this is the perfect place to visit!
#24. Tie a plastic horse to the curb
As you stroll through the neighborhoods of Portland you’ll start to notice the metal rings embedded in the sidewalks. These rings date back to the 1800’s when they were used to tie up horse carts. The Portland Horse Project began in 2005 when artist Scott Wayne Indiana began tying tiny horses to the unused rings. The movement took on a life of its own and soon people all over the city were tying tiny horses to the rings in their neighborhood.
#25. Watch the Roller Derby Girls get aggressive
Watch the “Break Neck Betties” take on the “Wheels of Justice” or the “Guns N Rollers” clash against “8 Wheel Assassins”. We’re talking about full body contact roller skating. We have been to several Rose City Roller Derby bouts and we still have no idea how this sport works, but they sell beer at the venue so who cares?
#26. Hike to the Witches Castle
The “Witches Castle” is a stone structure that was built in the 1930s as a park ranger station and a restroom for hikers. It was heavily damaged and is now covered in moss and graffiti and is a popular spot for teens to have parties on the weekends. There’s no connection to actual witches, it’s just a creepy old structure along a really beautiful hike in Forest Park.
From the Upper Macleay parking lot it’s about a half-mile hike to the Witches Castle or you can park at the Lower Macleay lot for a bit of a longer walk.
#27. See the swifts roost at Chapman School
Every year in late August thousands of Vaux’s Swifts gather in preparation to migrate to Central America and Venezuela. And one place in particular that one swift population has been choosing since the 1980’s is a chimney at Chapman School. Hundreds of people gather on the lawn at the school one hour before sunset to watch the swifts swooping through the air in unison.
#28. Make a wish at the Wishing Tree
This tree on Northeast Seventh Avenue has been a favorite for those looking to read the wishes of others or make their own wish for years. Jot yours down on a manila tag and tie it to the trunk. It’s sure to come true…
#29. Lounge naked at Collins Beach
Collins Beach is a clothing-optional sandy beach located on the Columbia River on Sauvie Island. If you aren’t a fan of tan lines you can bare it all without fear here. But please, for the sake of everyone around you, don’t act creepy and/or awkward. The best way to avoid being creepy is to lounge on Collins Beach in this:
While you’re there don’t miss the Collin’s Beach UFO Boat, a strange old UFO shaped boat abandoned and now covered in graffiti.
#30. Soak naked at Bagby Hot Springs
Bagby Hot Springs is a magical place tucked into the Mount Hood National Forest about 2 hours outside of Portland. An elaborate system of wooden aqueducts channels hot water into a collection of private and public soaking tubs hollowed out of old growth timber.
As with most Oregon hot springs, Bagby is a clothing optional soaking area. But be warned, the people exercising their right to exhibitionism are generally not the ones you would want to see naked.
#31. Burn your mouth on wings at Fire on the Mountain
Head to Fire on the Mountain for the El Jefe Challenge if you dare. You’ll need to eat 15 wings that are covered in their super spicy El Jefe sauce in less than 3 minutes. Your mouth will be on fire but if you do it you’ll get an El Jefe “survivor” t-shirt and your photo on the wall so… definitely worth it!
#32. Second-hand shop at Last Thursday on Alberta Street
First Thursday is an event in the Pearl district of Portland where people dress up to sip wine samples while browsing art galleries. Last Thursday on Alberta Street is almost the exact opposite. Grungy hippies fire dance in the streets, people dress up like gnomes, and stands selling bizarre art creations dominate the sidewalks. Last time I was there I almost bought an action figure that had a dinosaur head on a superman body. Almost…
Grab an outdoor table at one of the bars near 20th street for some epic people-watching.
You should check out First Thursday too, but it’s not even a little bit weird.
#33. Get drunk at the movies
There are quite a few second-run movie theaters in Portland where you can see movies that have been in theaters for a while at a fraction of the price. You can also purchase beer and wine at many of these. But the most popular venues in town belong to the McMenamins chain. You can count on them for good movies, comfy seating, piping hot pizza, and cold draft beer.
#34. Light your coffee on fire at Hubers
Established in 1879, Huber’s is the oldest restaurant in Portland. The restaurant is fine dining (i.e. expensive) but if you head to the bar in the back you’ll find a more casual atmosphere and the best Spanish coffee in Portland. And the servers make quite a show out of preparing your coffee. They will bring a tray to your table, light things on fire, and pour the alcohol into your glass from way above their head. Get your phone out, you’ll want to record this!
FYI – the Spanish coffee aficionados generally expect a tip.
#35. Dress up like Santa for Santacon
If you find yourself in Portland during the holiday season, you’re in luck. Hundreds of people dressed as Santa meet-up to begin a drunken, debaucherous pub crawl known as Santacon. You’ll meet a ton of new friends and have an absolute blast!
#36. Watch the Adult Soapbox Derby
Every year since 1997, Portlanders have been building coaster cars powered only by gravity to race down a hill at Mt. Tabor Park. It’s called the Adult Soapbox Derby and unlike some of the other things on this list, it actually IS fun for the whole family.
The car designs range from hilarious to extremely innovative and everything in between. Thousands of people gather to see the costumed teams competing for awards in speed, engineering, and other creative categories.
#37. Drink a beer while in detention at the Kennedy School
Kennedy School was actually an elementary school that has been converted into a hotel, complete with a movie theater and several bars and restaurants inside. McMenamins renovated the abandoned school to create one of the most unique spaces in all of Portland. Even if you don’t stay in one of the cute hotel rooms, it’s worth stopping by for a beer to check it out.
#38. Bounce on the dance floor at the Crystal Ballroom
The Crystal Ballroom is a music venue that regularly has live performances by popular bands. The dance floor is what makes this particular space special. It’s spring-loaded so when the place gets crowded and people start dancing, the floor really starts to move. It’s like dancing on a mattress with 500 strangers.
#39. Visit the statue that gave the show Portlandia it’s name
The Portlandia statue is the second largest copper repoussé statue in the United States. What is the largest you ask? The statue of Liberty, of course. You’ll find the Portlandia Statue perched above the entrance to the equally quirky postmodern Portland Building on SW 5th Avenue.
The Portland statue is also a popular stop for most Portland Walking Tours.
#40. Join a bike pub crawl
If you can get some friends together on a sunny afternoon, BrewCycle is a fun way to see the city and check out some Portland breweries. Or you can sign up on your own and make some new friends! Either way you’ll get some exercise while simultaneously getting a little drunk.
#41. Shop for book at Powell’s
If you can’t find the book that you’re looking for at the tiny community libraries, head to Powell’s Bookstore. With an inventory of over 2 million volumes, they are the largest independent bookstore in the world. The store actually occupies an entire city block! You can spend hours just wandering around, sipping coffee while browsing the impressive collection.
#42. Trade Books at a tiny community library
There are cute little “community libraries” in neighborhoods all around Portland where you can take a book if you leave a book. The book choices generally aren’t amazing but the tiny libraries are pretty creative.
#43. Pedal-power-blend your fruit shake at Moberi
Q: How do you combine food carts, bicycles, and farm-to-table eating? A: Moberi.
When Moberi first launched the only way to get one of their smoothies was to blend it up yourself on their bike-blender contraption. They have since added electricity to their carts so the pedaling is optional. Whether or not you choose to bike, their smoothies are made with fresh Willamette Valley produce and are refreshingly delicious!
#44. Walk across the no-cars-allowed bridge
The Tilikum Crossing Bridge is the first major bridge in the US that was designed to allow access to public transit vehicles, cyclists, and pedestrians – but not cars. The architecture of it is really beautiful, no doubt you’ll spot it immediately from the downtown waterfront.
#45. Go Zoobombing
There’s no question that Portland has an obsession with bicycles. But the Zoobombers take it one step further. Every Sunday evening they gather with their tiny tricked-out kids bikes, board the MAX (Portland’s light rail), and ride from downtown Portland to Washington Park station near the zoo. They then coast down through the West Hills back to their starting point where they all pile back onto the MAX and do it over again.
If you want to join in the fun but don’t have your own set of miniature wheels, don’t worry. They keep a collection of loner bikes piled up at the corner of 13th and Broadway (affectionately known as the “Zoobomb Pile”).
#46. Visit the Vacuum Museum
Since 1932 Stark’s Vacuums has been selling their namesake appliance and is one of the largest independent vacuum cleaner retailers in the country. But their real claim to fame is their oddball Vacuum Museum located inside of their flagship store on NE Grand Avenue. It used to house over 300 random pieces of vacuum-cleaning history but now the collection has been reduced to “25 of the most iconic and loved vacuums in history.”
#47. Shop at Paxton Gate
Shopping at Paxton Gate is like wandering through your weird uncle’s study. If you’re weird uncle was 50% Charles Darwin and 50% Indiana Jones. You can pick up anything from a fossilized Tyrannosaurus Rex tooth to a human skull. For the ultimate Portland souvenir inquire about their DIY taxidermy jackalope class.
#48. Get “laid” at a tiki bar
Portland winters can be long, wet, and gloomy. What better way to cure your winter woes than by sipping a fruity island cocktail while surrounded by tiki masks, taxidermied blowfish, and an indoor waterfall? Head to The Alibi Tiki Lounge to experience Portland’s most eclectic bar and most popular karaoke joint. There is no way you can miss the giant flashing neon sign as you’re cruising up Interstate Avenue.
If you’re heading to Portland in the winter make sure you pack accordingly!
#49. Drink at a Speakeasy
You’re liable to walk right past the Bible Club if you are strolling through the Sellwood neighborhood in SE Portland. From the outside it’s a nondescript residential house with the curtains drawn and no signage. But step through the front door and you’re transported to the 1900’s by a secret speakeasy bar serving up creative cocktails to those in-the-know.
#50. Check out the Zymoglyphic Museum
The Zymoglyphic Museum is a new entry to Portland’s ever growing list of eclectic museums and attractions. It claims to be “the world’s only institution devoted to the study and display of art, artifacts, and natural history of the Zymoglyphic region.” It’s a collection of the creations that artist Jim Stewart put on display in a curio cabinet fashion.
It’s only open on the second and fourth Sundays of the month but you can request a special viewing appointment by emailing the curator (AKA Jim) at email@example.com.
#51. Play pirate-themed glow-in-the-dark miniature golf
Pirate-themed glow-in-the-dark miniature golf is a lot of weirdness to take in, but it really does exist. And the cherry on top is that Glowing Greens is hidden in the basement of a boring old QDOBA Mexican Restaurant in downtown Portland. Make sure you get a pair of their 3D glasses to really make the experience disorienting.
#52. Sip coffee with some spirits
While we’re on the topic of the paranormal, Rimsky-Korsakoffee is Portland’s most haunted coffee house. It’s in an old Victorian House in Portland’s Buckman neighborhood. Patrons believe that the tables occasionally turn, ever so slowly. So when you reach down for your cup of coffee it has mysteriously rotated away from your seat.
Make sure you use the restroom while you’re there for an extra surprise!
#53. Embrace your inner child at Kidd’s Toy Museum
Equal parts interesting and creepy, Kidd’s Toy Museum houses a small selection of Frank Kidd’s massive collection of over 15,000 antique toys. The toys have been meticulously organized in dozens of glass display cases. To gain entrance to the museum knock firmly on the door, wait a bit, knock again a bit louder and hopefully Frank or his assistant, Julie, will come and let you in.
#54. Pair your wine with your astrological sign
Pairings Portland describes itself as “Portland’s weirdest wine shop and bar”. How can wine be weird you ask? Well, not only do they pair wine with food, but also with astrological signs, tv and movie characters, dog breeds, and songs. It’s a fun and approachable way to taste some wine and have some laughs while doing it!
#55. Listen to the acoustics at Pioneer Square
Pioneer Square is the center of downtown Portland – both physically and socially – and is always full of Portlanders eating lunch, reading, and chatting with friends. But what many people (even locals) don’t realize is that the square is also a giant echo chamber. If you stand on the inlaid plaque at the center of the amphitheater your voice will be amplified as if you’re speaking through a microphone.
While you are there get your picture with the famous “Allow Me” statue. He is more commonly known as “Umbrella Man” and is the most photographed man in Portland.
#56. Smoke and then sweat
Who doesn’t love to smoke a joint right before an aerobics class? Well, me, honestly. My preference is to devour a bag of Cheetos while watching Keeping up with the Kardashians. But if you do actually like to be productive when you’re high, then Mary Jane Fonda is the perfect class for you. DM them on Instagram for a class schedule.
So what are you waiting for? Get out there and start exploring Portland you weirdos!
Heading to Portland? Check out our favorite books!
SHARE THIS ON PINTEREST
Like What You Just Read?
Get epic story, travel guides, and pictures delivered straight to your inbox!