Keep Portland Weird: 19 things and places that define this city

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Keep portland weird 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. Read on and share with your friends.

The Zoobomb

The Zoobomb is a long-standing weekly Portland tradition that includes tiny bikes and a big hill. Yep, every Sunday in Portland you are able to 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.

Zoobomb in Portland, Oregon

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.

World Naked Bike Ride in Portland, Oregon

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!

Voodoo Doughnuts

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.

Perhaps Portland’s most famous local business, it 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.

Voodoo Doughnuts in Portland, Oregon

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. Why is Portland weird? Are you sensing a fun trend?

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.

PDX Adult Soap Box Derby

Dean’s Scene

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.

The Simpsons Connection

One of the most interesting things that many people will only start to notice about Portland once they know, is there is a strong connection with ‘The Simpsons’ cartoon. The cartoon’s creator Matt Groening is a Portland native, and while his inspired animation has been exported worldwide, it has a remarkable number of Simpsons connections. Many of the street names in the city have inspired the surnames of some of the characters in the cartoon, with NE Flanders Street giving the inspiration for Ned Flanders. Among the other streets that also made it into the show include Lovejoy, Van Houten, Terwilliger and Quimby. See how many you can spot!

The Paul Bunyan Statue

The story of Paul Bunyan is one that fits well into the origins of the city of Portland itself, as he is a larger than life logger who was said to have been amazingly productive. There are many tall tales about the man who was said to have created Minnesota’s 10,000 lakes with his footprints, while he is usually accompanied by Babe the giant blue ox that helps him in his work. So naturally, Portland adopted Paul Bunyan, when in 1959 they decided to build a 31 foot statue in his honor. This huge statue is in a cartoon-style rather than being too focused on the detail, and sees the logger in big boots, trousers and a check shirt, accompanied with this giant axe. Certainly a sight that could catch you off guard as you drive along the North Interstate.

Dean's Scene in Portland, Oregon

Photo via Flickr


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.

Glow In The Dark Mini Golf

Another of the businesses that probably wouldn’t thrive quite as well in any other city as it does in Portland. Glowing Greens is an indoor mini golf course with a difference, as blacklight is used to give the game an otherworldly atmosphere, with a definite scary theme.

The course itself is actually surprisingly well made, and the neon colors and the interesting lights make it fun for adults and kids alike. To really kick the experience into the next level, you can even hire 3D glasses to make for an even more dramatic experience as you put your way through the (unlucky!) 13 holes of the course.

neon indoor mini golf: weird things to do in portland

The Portland Saturday Market

Okay, so for most people a weekend market is something that happens in every town, and is not something that is of particular note. However, that is not the Portland Saturday market.

This bustling market covers an area of 5 blocks every Saturday, and is crammed with a fascinating combination of arts and crafts stalls, great street food and local producers, along with a wide range of street performers and musicians. The market is home to vendors that cover items that you never knew you needed, from jewelry that has been produced from old skateboards, through to a huge range of artists, including one that produces prints of Star Wars characters in unusual situations.

As you browse the market and try the food, keep an eye out for the live performers, as they can range from the ridiculous to the actually quite good. The Saturday Market has been running in Portland for close to 40 years, and is open from 11am until 4:30pm on the Naito Parkway.

The Bricks Of Pioneer Square

Pioneer Square is a large open public area that is in the heart of the downtown area of the city, and locals often refer to it as Portland’s living room because of all the social activities that take place there. However, it very nearly didn’t happen, as it had originally been earmarked for a large parking garage before the project to make a public space finally took off.

As the project hit financial issues, 50,000 local residents chipped in $15 apiece to help complete the project, but also had their names engraved on bricks that were used to pave the square. Indeed, it also became known as ‘Bang Heads Park’ because of the number of accidents as people bumped into each other trying to find the brick inscribed with their name.

Today this is a very cool place to hang out and relax, with regular events bringing people to the square. There are regular movie nights where family films are played on the big screen, along with free live music every Tuesday.


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!

Portlandia sketch comedy show about Portland, Oregon

Bonus Reasons — because 7 reasons to Keep Portland Weird just wasn’t enough. We need more odd 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. I don’t want to get into Portland vs. Austin though….

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.

Weird things to do in Portland, Oregon

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.

Weird things to do and see in Portland

Have you been to Portland before? What fun things have you done in Portland yourself?

Stay Weird Portland!


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.

keep portland weird

keep portland weird

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About Mimi McFadden

Mimi is the founder behind The Atlas Heart blog and has traveled through 4 continents since her first trip abroad at 18, including a two year stint living in Oceania. From jumping out of a plane in New Zealand, to eating snakes in Vietnam, learning how to cook in Italy, and scuba diving the Great Barrier Reef, she is always looking to live with an open mind and an Atlas Heart. She's currently based in the Pacific Northwest.