As soon as you rock into Portland, Oregon you’ll notice a unique vibe to the city, and the local’s pride in their weird nature and eccentricities. Maybe you think weird has a bad connotation but that’s not the case for Portland – think of it more as another word for lovable. There are tons of things to do and see in Portland, but more importantly, there are tons of WEIRD things to do in Portland (and plenty of free things to do in Portland as well) and we are about to review the best of the city right now.
The weird aspects about Portland are what draw people to it so often, it stands out from the crowd. There is a famous piece of street art that people search for near Old Town that says “Keep Portland Weird” and I couldn’t agree more, that weirdness has become the essence of the city. But to be fair, some say that Austin was the first to use the motto of keeping it weird, but let’s not argue over semantics.
Portland is home to the smallest park in the world, the most strip clubs per capita in the USA, is notorious for man buns, and that’s just hitting the surface. These are the other unique and random bits of Portland culture that fits their slogan to a tee.
The Zoobomb is a long-standing weekly Portland tradition that includes tiny bikes and a big hill. Yep, every Sunday in Portland you can go and join the zoobombers, called such because they all assemble at a big hill near the Oregon Zoo and bomb down it on kids’ bikes or minibikes. Anything unusual goes, so you could probably bring a unicycle if you desired. Weird?
The Zoobomb began in 2002 and has since become a much loved activity to do on Sunday nights in the city. Everyone takes their tiny bikes on the MAX Light Rail to Washington Park and then they proceed to the top of the West Hills near the zoo where they go as fast as possible down the hill. This is repeated usually about three times throughout the night with much socializing and drinking between rides before they stop for the night.
There is a local landmark in Portland called the Zoobomb pile where extra tiny bikes are piled up and tied to a pole. These are given to those zoobombers who don’t have their own bike for the night’s festivities but still want to participate. You have to love a city where the people come together like that.
World Naked Bike Ride
You can bet with a bicycle capital like Portland there would be more than just one type of fun cycling event in the city. The World Naked Bike Ride is next up with everything you’d imagine it to be. There are plenty of bits and pieces hanging out and good times to be had all around.
Although the concept is not new with many college campuses taking part in undie or naked runs before finals, this is a city-wide event that brings thousands of people to participate – most of them naked – personally I don’t think this is the best example of weird things to do in Portland… more like adventurous and fun things to do in Portland.
It began in 2004 as a protest against the use of cars and fossil fuels and it has only gotten bigger and better each year. This event is actually held in more than 20 countries and over 75 cities but Portland has the largest attendance out of any. If you want to experience the event make sure to be in Portland in late June!
Although not the best doughnuts you’ll find in Portland (that’s Blue Star!), Voodoo Doughnuts is the place that started the donut trend in Portland and its bright pink history offers up its own kind of Portland weird.
This famous shop is known for their crazy and out-there donut styles, like their popular bacon maple and even a cream filled donut that is in the shape of a voodoo doll with a pretzel sticking out of it.
As a late-night donut shop they’ve always catered to the nightlife clientele, which is why they used to have donuts such as the NyQuil Glazed doughnut and the Vanilla Pepto Crushed Tums doughnut. These are no longer available due to the health hazards involved with selling over-the-counter drug-laced donuts, but still, it makes for a hilarious story. Rumor has it that the Pepto doughnut was the inspiration behind their bright pink packaging.
If you time it right you can sometimes find little to no line at the Old Town location, but a lot of times there is a line around the block. It’s cash only, so remember to have some dollars before you wait in line for half an hour.
PDX Adult Soap Box Derby
Every year in August Portlanders get together to put on the Adult Soap Box Derby to the glee of a public audience. The derby is located on the scenic extinct volcano that is Mt. Tabor Park, where participants create colorful homemade contraptions on wheels to fly down a big hill on. Are you noticing a trend yet in Portland?
Last year there was a group of 3 who flew down the hill on a giant hot dog on wheels. Things definitely get interesting at the summer Soap Box Derby! It’s a free event and beer and picnic fixings are welcome, as well as water balloons to throw at the participants.
Dean’s Scene is a bar located in the basement of a middle-aged dude who brews his own beer. It’s not technically a bar since there is no liquor license for the place, but it’s seen as a local speakeasy of sorts. How he gets around the liquor license issue is by asking for cash donations at the door, about $5, and then giving you free reign to have as much beer as you see fit.
Since it’s still considered a private household, there is also marijuana available to be smoked since that is now legal in Oregon. Dean once even brewed a weed beer which was the talk of the town for awhile. This place is popular with a varied crowd and the only common denominator you can count on is that people who go to Dean’s Scene love beer. If you can find it, this is definitely worth a stop to experience an alternative side to Portland’s bar scene, call it the Keep Portland Weird Smoke Scene.
It’s no coincidence that Portland has the highest number of strip clubs per capita in all of the States. This city loves its strippers and free expression no matter what form it comes in. The weirdest Portland strip club you may come across may just be Devil’s Point, which offers up a chance to sing karaoke that strippers will dance to.
It could be your worst nightmare or the best night ever, but regardless of how you feel about hearing your own voice as a soundtrack to a lady stripping, you’re bound to have an interesting and slightly weird night at Devil’s Point.
And lastly there is even a weird, quirky and sometimes funny sketch comedy show about Portland called Portlandia. You’ll be surprised at how even though its an over exaggeration of the culture here, it’s not off by much!
Bonus Reasons — because 7 reasons to Keep Portland Weird just wasn’t enough. We need more weird things to do in Portland to insure your interest in one of our favorite cities in the world.
History of “Keep Portland Weird”
The “Keep Portland Weird” movement started when Terry Currier, owner of the famous music store Music Millennium, learned of the movement that started in Austin and brought it to Portland in 2003. In 2007, he trademarked the phrase and and sold more than 10,000 stickers by the end of that year alone.
Stark’s Vacuum Museum
Yes, Portland has a museum dedicated to the mundane and boring life task of vacuuming. Does it get any weirder than that?
The last time I vacuumed my apartment, the very, very last thing on my mind was going to a place dedicated to reflecting and emphasizing the importance of keeping my floors clean. Of that various weird things to do in Portland, count me out on this one permanently.
A vegan strip club
Yes, Vegans are plentiful in the Portland area. How plentiful are they, do you ask? Well, there are enough of them that they make up the entire clientele of the Casa Diablo, which is not only a vegan strip club… it is vampire themed.
Although I am far from a vegan, this is one of the weird things to do in Portland that both of us are going to enjoy next time we go there.
The Shanghai Tunnels
The Old Portland Underground, which is known locally as the Shanghai Tunnels, is a group of passages in Portland, Oregon, mainly underneath the Old Town Chinatown neighborhood and connecting that areato the main business section of town.
There is a bit of a dark and mysterious past to these tunnels — you see, rumors have it that people were dragged off their barstools and sold into slavery after being kidnapped and drug off underground.
Here’s an example of weird things to do in Portland… NOT. Thank goodness it is confined to the dustbin of history.
The Horse Project
Random tiny toy horses are found on sidewalks, at bus stops, and in parks tethered to old horse rings.
Not much more to be said about that… just another example of cool things to see in Portland. Or perhaps art in the streets?
World’s Smallest Park
We mentioned it above, but you need to see a picture to believe it. If there is a better example of Portland’s spirit, I’ll need to see it.
Have you been to Portland before? What fun things have you done in Portland yourself?
Mimi founded The Atlas Heart to create a community of travelers inspired to see the world. Follow her on The Atlas Heart for more great stories and photos of a worldwide adventurer.