Weird (But Cool) Portland Places


Welcome to Portland – where being weird is normal and being normal is unheard of. The truth is, Portland is the single weirdest city on Earth, and Portlandians take that seriously.

Every other car in the City of Roses has a bumper sticker saying “Keep Portland Weird.” So today, in honor of Portland’s weirdness, we’re going to talk about the freakiest places you can venture to in the City of Roses.

To avoid spoiling too much about any one attraction and to highlight a multitude of weird but cool options for you and your Portland crew, I’ll keep the descriptions short. Oh, and be sure to check out these vacation rentals in Portland, OR, to find the perfect home base for you and yours.

The Freakybuttrue Peculiarium

This is one museum that is not kid-friendly. At the Freakybuttrue Peculiarium, horror abounds and each exhibit is more twisted than the last. Take in the spider-featured artwork, the anxiety-inducing screen displays, and finally some tasty treats from the Peculiarium’s ice cream parlor. It’s weird, it’s cool, you should go. 

Cuddle Up to Me

Okay, so maybe the Peculiarium wasn’t the way to start your Portland adventure. That was a little too intense – my bad. Let’s chat about something that’s just as weird but a whole lot more wholesome.

Cuddle Up to Me is a business that lets you snuggle with a “professional cuddler” for anywhere from one to five hours. Whether you’re a little spoon, a big spoon, or some other kind of snuggler, Cuddle Up to Me is here to provide some soothing physical contact. Partners can even come in together to learn new cuddle techniques!

Funhouse Lounge

The Funhouse Lounge is the perfect kind of extremely weird: the kind that comes with alcohol and karaoke. The lounge acts as a bar, a comedy venue, and a performance space, and the whole thing is circus themed.

Do you suffer from coulrophobia, a.k.a. clown fear? You will. All you have to do to develop coulrophobia is spend ~5 seconds in the Funhouse Lounge’s Clown Room. I’ll repeat that. Clown Room. As in, a room solely dedicated to clowns.

And these are some “It” level clowns, not like the one your mom hired for your 8th birthday party. Enter the Clown Room at your own risk.

Pittock Mansion

Originally constructed in 1914, Pittock Mansion is the closest thing you can get to a “normal” tourist site on this list. This century-old mansion sits on 46 acres of lush grounds. Located in the middle of Washington Park, Pittock Mansion is an excellent stopping point for anyone with an interest in history, architecture, or bird watching. The mansion was opened to the public in 1965 after being purchased by the city, so feel free to take your time exploring nearly 50 separate rooms within the building.

The Witch’s Castle

Aside from being constructed in ye olden times, The Witch’s Castle is basically the polar opposite of Pittock Mansion. This roofless and long-abandoned building is steeped in rumors of mystery and murder. This is the perfect place for photographers to get some impressive nature shots, and The Witch’s Castle is a cool place to hang out in general. It’s pretty unlikely you’ll get murdered at The Witch’s Castle, but do be careful to avoid bears and other hazards during the ¾ mile hike to the structure.

Voodoo Doughnuts

Every little girl dreams about her wedding day. The fancy outfit, the adoring spouse, the festive decorations, the doughnut shop owner presiding over every perfect second. Wait, what?

Yes, that’s right–you can now get married in a doughnut shop. Believe it or not, while Voodoo’s primary selling point is its famously delicious and creative pastries, the store also sells a variety of wedding packages.

Each package comes replete with doughnuts and refreshments, of course. Simpler yet, just grab yourself whichever unique pastry catches your eye first and just enjoy some hassle-free sugar.

Mill Ends Park

The last entry on our list is also our shortest, and with good reason. Mill Ends Park is quite literally the smallest park in the world. At a whopping 452 square inches, the park earned its tiny spot in the Guinness Book of World Records.

As you might imagine about a park only a couple feet in size, there’s not exactly a lot to do. In truth, the only reason to visit this park is so you can go home and tell your friends you went to the smallest park in the world. But hey, bragging rights still count for something, right?

Have you been to Portland? 



About Author

Kelly Lewis is the founder of Go! Girl Guides, the Women's Travel Fest and Damesly. She's an optimist, an adventurer, an author and works to help women travel the world.

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