Keeping it weird: 16 weirdest Portland attractions to see when you visit

Mar 9 2020, 3:14 pm

Do you really ever need a reason to book a vacation? We don’t think so.

The good news is that you don’t have to spend 12 hours travelling to the other side of the world to enjoy a different kind of getaway. That’s because an intriguing, weird, and wonderful destination is located not far from Vancouver:¬†Portland.

The shipping port city is dubbed a hipster hotspot due to local liberal attitudes and the sheer selection of things that you can’t find in any other US city ‚ÄĒ and that’s what makes it so fun to visit. It’s lively, eclectic, and the kind of place that most people want to see more than once.

So, with that in mind, we’ve teamed up with WestJet¬†to showcase some of the weirdest things see and do in Portland when you visit.



Portlanders appreciate good food, and the city is home to some of the best eats on the west coast. Since it’s always worth mentioning dessert before dinner, the local doughnut scene is especially noteworthy. Blue Star Donuts (thank you, American spelling) has seven locations in Portland, serving up sweet, seasonal, and vegan doughy treats. Do yourself a favour and try the passion fruit cocoa nib doughnut.

Specific late-night food cravings often hit us, and when they do, 24-hour diner¬†The Roxy is the place to go. Stop by at any time of the day or night to order breakfast, pancakes, nachos, fries, or anything else on the lengthy menu. Fun fact: “Keeping Portland Weird Since 1994” is the diner’s tagline.

For meat lovers,¬†The People’s Pig¬†is a popular choice where chefs cook up the most delicious, melt-in-your-mouth beef brisket in town (a Portland staple).



You’ll never be bored during a trip to Portland because the list of quirky attractions is endless. Consider yourself a cleaning aficionado? A visit to Stark’s Vaccum Museum¬†has got to be top of your list. Learn about the history of the vacuum and see the most loved models of all time.

To explore strange and creepy exhibits that celebrate sci-fi and urban legends, check out The Freakybuttrue Peculiarium and Museum¬†on Thurman Street. Keep those spooky vibes going by visiting The Witch’s Castle on the Lower Macleay Trail. The ruins are reportedly haunted, but you’ll have to hike the half-mile there to see for yourself.

Did you know that Portland has underground tunnels? Take a tour deep beneath the city to discover what they were once used for. Once back on the surface, drink in epic skyline views from the lookout at Renaissance-style ch√Ęteau Pittock Mansion.

Don’t forget a bizarre musical experience at¬†Quarterworld¬†pinball and arcade palace on the Eastside. You’ll even find a musician playing the Tesla Coil (an electrical transformer circuit) as an instrument.


Workshop Vintage/Instagram

Need new spring wardrobe essentials? It’s worth waiting until you arrive in Portland to go shopping because the entire state of Oregon is tax-free ‚ÄĒ with discount outlets on top of that.

In the city, there are thrift and artisanal stores galore where you’ll find charming, unique items. For vintage clothing and accessories, visit Red Fox Vintage or Workshop Vintage.¬†Boys Fort has locally-made treasures like bags, wallets, and grooming products for the guys. And although you might not want to fill your luggage with homewares, Woonwinkel¬†is a beautiful store for browsing where you can pick up a dainty home accessory or two.

For any and all book lovers interested in visiting Portland, be sure to check out the world’s largest independent bookstore, Powell’s Books, and pick up a read for the flight home.


Ground Kontrol Classic Arcade/Orange Photography

Nightlife in Portland is unlike anything in Vancouver, and there are some very interesting places to go for drinks.

For instance, themed bars are extremely popular¬†in the city. Funhouse Lounge¬†on the corner of¬†SE 11th and Division is a prime example. It’s a wild cabaret of sorts where you can grab a drink and take in entertainment ranging from comedy to burlesque, to storytelling. Oh, it was also voted one of “Portland’s Weirdest Bars.”

Meanwhile, Ground Kontrol¬†is a fun-time arcade where visitors can order drinks like the princess peach cocktail and play games until close (usually 2 am). Couch Street has the intimate¬†Big Legrowlski¬†(sound semi-familiar?) beer and cocktail bar where you can catch a live music show ‚ÄĒ and¬†take it easy.

Feeling inspired to visit Portland yet? We’ve only touched the surface of incredibly weird and fun things to do in this Oregon city; you’ll discover the rest when you get there.

WestJet offers connecting flights to Portland from Vancouver and flies non-stop to Portland from Calgary. Book your flights at now or through your travel agent.

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