The Best Guide to All Things Weird in Portland Oregon

Last Updated:   1/11/2017

The dream of the 90’s is alive in Portland, so if that inner hipster in you hasn’t found its place to call home, or you’re missing a good dose of WEIRD, perhaps it’s time to relocate to greener (or rainier) pastures. By the way, if you don’t recognize the first sentence or any of the pictures above, you really don’t know Portland THAT well. (Tip:  it’s from the show Portlandia, and for those of you who ask me constantly, YES some of the scenes in Portlandia are very true to life!)  I’ve read that Austin, Texas and most recently Pittsburgh, Pennsylvania are contending for the title of best hipster city, but let’s be real:  Portland is the OG. Portland was hipster before people knew what hipster was.  Now they’re gladly willing to pass on the title to keep people from moving to Oregon.

Here’s a little backstory. I lived there for 3 years of my life, and visit quite often because my family is based in Oregon, but if I’m being honest, I had to leave because the influx of rainy, but more so GRAY days, left me with a real case of seasonal affective disorder. Hey, Portlanders deserve legal weed for that kind of suffering! That said, I had no idea how weird Portland was until I left. Wait, you mean not all cities have funky cock and ball doughnuts (ala Voodoo) stacks of bicycles in the middle of nowhere, a Darth Vadar bagpipe blowing and unicycle riding icon, a professional cuddler that was featured on America’s Got Talent, a cat cafe, an annual naked bicycling ride, a music venue with a “floating” dancefloor , a hotel that leaves condoms on the nightstand and a nude beach with a UFO?  Hmm, no wonder I felt so at home in Venice Beach. (the other weirdest place I’ve ever lived in my life)

The Crystal Ballroom 


Credit:  @CrystalBallroom on Instagram

We’ll begin with one of the most unique and historic music venues I’ve ever encountered in my life. If you haven’t had a chance to dance 80’s or rock your brains out at the Crystal Ballroom you really haven’t lived. Why? Because the main ballroom features a mechanical “floating” or sprung dance floor that I like to refer to as the bouncy floor.  Trying to describe it to someone who has never experienced it is difficult, so I’ll just say this: GO THERE!

The majestic century old ballroom is entrenched with Portland flair and one can almost hear the echoes of past concert goers screams. There’s even an urban legend which states that Jimi Hendrix was once fired on the stage for his supposed lack of skill, so if that doesn’t give you motivation to succeed I don’t know what will! After you dance your pants off, you’ll surely be thirsty enough to toss back a beer.  Lucky for you, the Crystal Ballroom is a McMenamins property, and if you just head right upstairs you can wet your whistle at the most iconic bar in the Portland region. If you get tired of that scene but really like McMenanmins beer, make sure you hit the next spot on my list.

Historic Edgefield


Edgefield is another hot spot that combines a multitude of fun activities but certainly has a few weird and offbeat claims to fame. I’m not even sure if you’re a true Oregonian if you haven’t taken in a show at Edgefield during the summer sipping on a ruby from McMenamins.  Edgefield functions as a brewery, hotel, and venue, and includes a golf course, plenty of art, a soaking pool, a movie theater, and even more! Rumor has it the ghosts there love when you come to visit, which makes the fact that there are no tv’s or phones in the room that much creepier.

Jupiter Hotel


MoscaPhoto - Event & Corporate Photographer © http://www.moscaphoto.com

Credit:  MoscaPhoto – Event & Corporate Photographer © http://www.moscaphoto.com

To continue your weird Portland parade, why not take a pit stop at the Jupiter Hotel and stay there for the night?  This funky and extremely retro pop-artsy type hotel is definitely attuned to those who live outside the box. There are condoms on the nightstand for your pleasure, and in some rooms, you can even take chalk and draw all over the walls.  Let the kid in you run wild and make up for all the times someone stifled your genius wall masterpiece.

Purrington Cat Lounge


Credit:  @Purrington Cat Lounge on Instagram

Folks, you don’t have to go to Japan to experience a cat cafe. Purrington’s Cat Cafe is the first cat cafe in portland bringing people and cats together!  The cats are hand picked by the shelter partner Cat Adoption team to ensure they are appropriate for the environment. On one side of the cafe is the cat lounge, and on the other is the cafe, so that you can easily go between both, but also view the cats through the window. Quite possibly the best part of all of this?  On some days they hold Purr Yoga. I bet you can’t guess what that is! (hint: it’s yoga with your cats silly bird)

Weird Portland Adult Soapbox Derby


Portland’s PDX adult soap box derby is a 100+ volunteer fueled grassroots community event usually held the 3rd Saturday in August at Mt. Tabor. You really don’t know how weird Portland can be until you’ve seen creative juices collide at an event like this with up to 5,000 people.  By the way, you’d be doing a huge disservice to yourself by not checking out the history of how this derby came to fruition.

Joe’s Donut Shop


I don’t know about you, but all of this weird Portland talk is making me hungry!  What do you say we head across town to the suburb of Sandy and eat a delicious doughnut? Notice I didn’t mention Voodoo Doughnuts again, because to be frank, I believe Voodoo is a bit overrated, even thought it’s weird. (I hope I don’t get hipster hate mail for this)  Besides that, if you go to Joe’s for Doughnuts, you get to see the infamous Sandy spoon man which is what makes it weird in the first place!

Slappy Cakes


Or would you prefer to hit brunch, because we all know how much people in Portland like to brunch. Very well then, let’s hit Slappy Cakes, the only place where you can make your own pancakes and eat breakfast all day. PSA:  I’d like to take this moment to let restaurants know they SHOULD ALL be serving breakfast all day! Anyhow, Slappy Cakes is awesome because you can also have an adult beverage there, which let’s face it, makes the whole making your own pancake experience that much more pleasurable.

Le Bistro Montage


Should you desire food that’s a little more eccentric, be sure to check out le bistro Montage! You know, the place everyone hits after bar hours that serves spicy macoroni and cheese, frog legs and gator bites!  The best part of Montage, well besides the food, is that they take your leftovers and turn it into foil art like the picture above!

Weird Portland Naked Bike Ride


Alright, now that you’ve chowed down, next stop on our tour is the Portland naked bike ride! This event, which draws thousands of people, is the beating heart of Portland filled with stark naked pride. To be fair, this event does occur in a few other cities, but we’re going to pretend Portland’s is the best. Also, the website states that if you think you’re going to an orgy you should think twice. The nudity is merely a way to draw attention to cyclists and laugh in the face of oil dependence.  For more info, check out the FAQ!

Sauvies Island



Credit:  Erik Graham photography


I had to include this one on the list because as most Portlanders know, it’s one of only two nude beaches in the Portland area. However, it’s under consensus that most of the naked people there are generally people you REALLY DON’T want to see naked. But there is something that I discovered in my research some of you Portlanders may not even know. Have you heard of the Sauvies Island spaceship?  Okay, so maybe it’s not REALLY a spaceship so much as a boat that washed up on the beach in the 1960’s. Go find that bad boy!

Women’s Lube Wrestling


We’re nearing the end of the tour, but don’t fret, I’ve got tips for a weird event coming up at the end of the month in Portland! Rumor has it from my friend Audrey at Audreality there will be women’s lube wrestling held at the Analog Theater on February 27th! It’s only $12 and supports the women’s rugby team so get there! I will let you know whether this will become an annual event!

If you find all of this offbeat and weird Portland doesn’t satisfy you, then maybe you should go see the the Sinferno Cabaret at Dante’s, the Rocky Horror Picture Show, visit the underground world at Shanghai Tunnels for some ghost adventures, or travel a little down the road from Portland to the Mt Angel Abbey and Seminary to see the largest hairball in the world that Chuck Palahniuk (a Portland ICON) made famous in his book Fugitives and Refugees. Word has it, the place is really eerie!

Well, I hope you’ve had enough weird Portland for one day because I’m exhausted!

Are there any weird Portland activities you’d love to check out?! OR are there any Portland activities you’d probably never do!? 









27 thoughts on “The Best Guide to All Things Weird in Portland Oregon

  1. Elizabeth O.

    Haha! I love that this is all about the weird stuff. We don’t get a lot of guides about that in places that are fun to visit! Thanks for sharing all the things you can do! So much fun!

  2. Laurie

    I have a friend that lives in that area. If I get the chance to go visit I’ll remember to check out these places you suggested

  3. Jaime

    I haven’t been to Portland in a LONG time but I’ve always loved it. I love doing the odd and weird and… I might have to experience these! LOL

  4. Shaylee

    I’ve never been to Portland but would LOVE to go! All of these things so like so much fun! I’m not sure if I could ride a bike naked (mostly because it sounds uncomfortable) but everything else is right up my alley – especially cat yoga!

  5. Kiwi

    Wow I legit didnt know Portland was this weird with all of these activities. Jupiter Hotel with the condoms on the nightstand lol, Naked Bike Race lol, Woman Lube Wrestling…wow this is a very interesting placE!!

  6. Therie

    Yoga with cats doesn’t seem really weird to a cat lover like me! I’ve never heard of any of these events and activities in Portland before. This is really interesting!

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