Despite the fact that “Keep Portland Weird” has only been the city’s unofficial motto for less than two decades (introduced in 2003 as a local business support initiative), Portland has adopted the adage and takes pride in being called quirky.

But what makes Portland weird, you may ask?

If you’ve ever been to Portland, you’ll know that the city is full of eccentricities. It’s a city that allows weddings in a donut shop and hosts festivals wherein bikers are only in their birthday suits.

Strange aspects of Portland define the city in general. In fact, Being referred to as a “weird city” is not an insult to us residents; rather, it is a compliment.

We have the smallest park in the world, the most strip clubs per capita in the United States, and deliciously strange new types of doughnuts, to name a few things (we will explain all of these later).

However, this is only the tip of the iceberg. Want to learn more about what makes Portland weird? We’ve rounded it all up for you!

1. The city takes cycling to new heights

Portland hosts a plethora of strange bicycle-themed events all year long. The Zoobomb is a long-standing (every Sunday) Portland custom that involves little bikes and a steep hill – but what makes it strange, exactly?

The zoobombers gather at a large hill near the Oregon Zoo and ride tiny children’s bicycles down it. The zoobomb signature is tiny bikes, and the smaller the wheels, the more glorious the rider. 

The ride is usually repeated three times throughout the night, with much socializing and drinking in between rides, before they call it a night.

The World Naked Bike Ride is another event worth mentioning. It takes place in over 75 cities and over 20 countries, but Portland draws the biggest crowd. 

Although it may seem silly, hundreds of people gather naked for the ride every June to raise awareness of how vulnerable cyclists are on the roads.

If you don’t want to ride in the open, you can join the Worst Day of the Year bike ride. We’re guessing you already know what it entails based on the name!

Since it was allegedly timed for the worst weather day of the year, the ride has been referred to as a statement to get over the awful and depressing feeling that the weather may bring. This usually happens in the month of February.

2. The city hosts a number of strange festivals

As if an odd bike ride wasn’t enough, Portland hosts strange events and festivals throughout the year as well.

Every May, thousands of people flock to McMinnville, an hour southwest of Portland, to attend the city’s famous UFO Festival. Weird but intriguing, right? 

Well, the festival began in 1999 as a way to commemorate the famous Trent sighting in 1950 and has since grown into an epic celebration of all things extraterrestrial. 

Now, this annual alien jubilee includes two days of special events such as live music, expert speaker panels, a pet alien costume contest, and other activities.

Meanwhile, the Faux Film Festival is a comedy festival dedicated to parodying and celebrating the film industry. It’s the world’s only festival dedicated to spoofs, satires, documentaries, music video parodies, fake trailers, fake commercials, and so on. 

Although it’s not really a festival, Portlanders come together every August to host the Adult Soap Box Derby at Mt. Tabor Park. Here, a few teams of kids-at-heart adults drive homemade soap box derby cars down a steep hill. 

Miniature Batmobiles, A-Team vans, and the ever-popular Flintstones cars have all been featured as vehicles. People gather along the track to watch the daring speedsters while enjoying picnics with their own beer and wine.

3. The connection with “The Simpsons” cartoon

Fans of The Simpsons may already be aware of this, but Portland has a close relationship with the animated series. Its creator, Matt Groening, is a Portland native.

Matt Groening was just another kid in Portland, living on Evergreen Terrace, long before he became the creator of the longest-running US primetime television series in history. Yes, the fictional Springfield, where the Simpsons live in the show.

Not only that, but many of the city’s street names are the surnames of some of the cartoon’s characters. This is not a coincidence – Groening simply thought it would be amusing to name the Simpsons characters after streets in his hometown.

Ned Flanders, the Simpsons’ devout neighbor, was named after Northeast Flanders Street in Northeast Portland. Schoolyard bully Kearney Zzyzwicz’s namesake is none other than Northwest Kearney Street. 

Even the name Montgomery Burns is a combination of two Portland landmarks: Burnside Street and Montgomery Park.

To name more personas, Reverend Lovejoy was named after NW Lovejoy Street, and Sideshow Bob’s surname is Terwilliger, after a Portland street in SW Portland and the Terwilliger Curves. 

4. There’s a 21-foot-tall chocolate waterfall

Portland, Oregon is well-known for its proximity to stunning waterfalls, and it appears that the city can’t get enough of them. And of course, we can’t talk enough about our new favorite waterfall, and it comes with a sweet surprise and is a tall one.

The Candy Basket has its very own chocolate waterfall. It’s a 21-foot-tall waterfall cascade of Guittard chocolate that looks and smells incredible.

However, you shouldn’t try to slurp the chocolate from the fountain! Let’s just say that the 2,700 pounds of liquid chocolate that have been flowing through the fountain for several years is made to cascade smoothly rather than to taste good.

Fortunately, you are at the entrance to a chocolate-filled shop. The outlet store’s large cases are stocked with hand-dipped chocolates of every variety (even chocolate-dipped potato chips are available here).

Take a tour of the factory just in case you run out of chocolate to purchase. The Factory Outlet Store for The Candy Basket is situated at 1924 NE 181st Ave. in Portland, Oregon – open daily!

5. Stripperoke is a thing

It’s no secret that Portland, Oregon, is the strippiest city in America. It actually has the most strip clubs per capita in the United States, earning the name of the strip club capital in the country. 

Speaking of which, the Devil’s Point strip club allows you to sing karaoke to which strippers will dance. Stripperoke, as they called it – a combination of a strip club and karaoke.

Shon Boulden, the club’s co-owner, stated that the concept began in 2005 when they were simply having a regular Sunday night with three to four girls working. They became bored and decided to go karaoke.

It was originally known as “Karaoke Sabbath,” but words were crammed together and it became known as “stripperoke.”

Devil’s Point is arranged like a live music venue, as opposed to many strip clubs, which have a dance stage in the center for performances. Every Sunday, the club is packed with patrons who sing while the ladies strip to it. 

Well, it might either be the worst or the best night of your life. Regardless, a night at Devil’s Point is sure to be interesting and a little strange.

6. And if that’s not weird enough, the city has a vegan strip club

Portland is undoubtedly a vegan-friendly city. Numerous restaurants – including Off the Griddle, Epif, and Blossoming Lotus – offer vegan-friendly menus.

And, because there is literally something for everyone in the city, strip club hoppers who are also vegans have a place to go – the Casa Diablo.

The establishment is, well… sketchy, lacking even the façade of a “gentlemen’s club,” but the bartenders are topless, and the dancers completely strip off and are told to sit on patrons’ laps.

Just to give you some background, Casa Diablo was once a vegan family restaurant by the name of Pirates Tavern. However, workers in northwest Portland found it unappealing because they preferred some action with their salad. 

That’s why the owner, Johnny Diablo, took notice and relaunched the restaurant as Casa Diablo Vegan Strip Club.

In the strangest way imaginable, non-human animals are treated with more respect in Casa Diablo than the strippers (yikes, we know). 

The establishment has even received criticism and even legal action from people who claim it trades the exploitation of animals for the exploitation of women. As their sign reads – “Please do not wear fur, feathers, silk, wool, or leather on the stage. Thank you – the animals.“

7. There are museums dedicated to unusual things

If we are talking about weird museums that can be found in Portland (which there are), The Freakybuttrue Peculiarium and Museum is definitely at the top of the list.

This Peculiarium in Portland is definitely weird and worth at least 30 minutes of entertainment (if you’re looking for weird things to do). After all, it is home to a spooky assortment of oddities, including rooms covered in blood and a bath filled with what appear to be human organs. 

They also have exhibits featuring urban legends and totally immersive experiences, such as what it’s like to be buried alive.

After you’ve finished your tour of the Peculiarium, stop by their gift shop. Customers are greeted by a massive Bigfoot statue, and the shelves are crammed with strange pop artifacts, cheap gag toys, and creepy specimens.

For those who do not have a strong stomach, the Stark Vacuum Museum is the one for you. Yes, there is a museum in Portland dedicated to the mundane and boring life task of vacuuming. 

Their wall on the main floor is decorated with dozens of classic vacuums, as well as a timeline from 1876 to 1970 that highlights some of the vacuum industry’s most fascinating moments.

Stark has 300 vacuums in its collection, all of which were donated or sent by people who didn’t want to throw away their old machines. That’s why visiting this museum is certainly a quick stop, plus it’s free, so this weirdness is definitely worth checking out.

8. The city has haunted tunnels beneath it

Tourists flock to downtown Portland’s shops and restaurants, completely unaware of what lies beneath their feet. 

A series of 150-year-old tunnels beneath the ground connects the basements of Portland’s oldest buildings to the Willamette River and Portland’s Chinatown. What’s so scary about that?

These tunnels have a dark and mysterious history. Rumors say that people were dragged off their barstools and sold into slavery after being kidnapped and drugged underground. 

Travelers today report feeling goosebumps deep within the tunnels as if someone is watching them from the shadows. While others recall feeling unwelcome. 

If you’re into that sort of thing, you can sign up for a tunnel tour. Just be prepared for total darkness and stay with your group at all times!

9. You can get married in a donut shop

The Voodoo Doughnut is perhaps Portland’s most well-known local business. It is, after all, the place that started the Portland donut trend, and its bright pink history offers its own brand of Portland weirdness.

However, did you know that you can get married at their shop in addition to getting crazy and out-there donut styles? The store has a marriage license, so it is completely legal!

For those interested couples, their wedding packages start at $300 and include doughnut replicas of the newlyweds as well as a celebratory sprinkle shower. 

Don’t forget to include odd-looking doughnuts on your menu, like their cream-filled voodoo doll with a pretzel sticking out of it. That would be fun!

10. It’s home to the world’s smallest park

Having the world’s smallest park is “so Portland.” Mills End Park, the Guinness World Record holder, is only two feet across.

This park, located in the median strip of SE Naito Parkway in downtown Portland, has been the smallest park in the world since it was awarded the designation in 1971. And it officially became a park on St. Patrick’s Day in 1976.

For a quick backstory, Dick Fagen was the man behind the park’s creation in 1946. He was curious about the unused hole in the median from his office, which overlooked the Naito Parkway (at the time, Front Street). 

Dick took ownership of the hole and began planting flowers in it. He also began a column called “Mill Ends,” in which he discussed park events.

Many people have since made improvements to the park. There’s a small swimming pool, a butterfly diving board, numerous statues, and even a miniature Ferris wheel. 

Despite its size, it is treated like any other park, with events and concerts held throughout the year, including St. Patrick’s Day celebrations.

Now that you’ve learned a few of the things that make (or rather keep) Portland weird, we get a sense that you couldn’t agree more with our city’s unofficial motto, “Keep Portland Weird.”

This is just the tip of the iceberg, by the way. There are still tons of other fun activities to do in Portland that can give you a weird vibe. That weirdness has become the essence of the city, so don’t hesitate to visit and experience it firsthand. 

Keep it weird, Portland!