Since the advent of a certain IFC show starring a member of Sleater-Kinney, Portland has been mythologised as a town built on nothing but whimsy and underemployment. But like any city, the reality is more complicated and a lot more enjoyable.
Portland’s the kind of city where you can learn to bike-commute without fear, where bookstores rule and indie publishing thrives. It’s also the home of the Decemberists, Cheryl Strayed, Chuck Klosterman, Stephen Malkmus, the other two members of Sleater-Kinney, and, when it comes right down to it, some pretty fascinating city politics.
Its casually gorgeous riverfront bike trail and its transit-friendly navigability, there’s much to love about Portland. And Portland will love you back, if you let it.
If your only goal in taking a trip to Portland is to get your picture taken in front the ‘Keep Portland Weird’ mural, be my guest. You won’t need my help finding it, and it won’t give you a real sense of the place, beyond the parts of it most easily reduced to caricature.
But if you’re interested in getting to know what endears Portland to the people who live there, here’s where to start. Just remember to keep your preconceived notions and your ‘Put a bird on it’ jokes to yourself.
A culture of resistance
Portland is a beautiful city bisected by the Willamette River. It is home to iconic public art such as the Portlandia statue. Few commutes are prettier than the ride over the Broadway Bridge on a clear day, when Mount Hood is out, or biking down the Eastbank Esplanade at sunset. But many of the photos I have from my time in Portland were taken at protests.
This is partly circumstantial covering protests was part of my job when I lived there but it’s also just Portland. Portland is a city that can always be relied upon to show up in the face of injustice (or perceived injustice) with civic-minded, contrarian panache and an undying streak of creativity.
Portlanders have protested everything from a Shell Oil icebreaker ship bound for the Arctic in to vaccines.
Perhaps most famously, Portland mounted one of several protests nationwide the day after the 2016 presidential election. Property damage incurred by a splinter group of anarchists made headlines. What was less publicised was the peaceful rally beforehand, and that in the same week, one of the protest’s organising groups raised $32,000 to repair the damage they hadn’t caused.
Two months later, the city’s Women’s March drew 100,000 attendees, according to estimates reported to The Oregonian. Not bad for a city whose population numbers less than 650,000, and not surprising for Portland.
Portland’s culture of resistance is indicative of a rare level of civic engagement you don’t find everywhere. For better or for worse, it’s part of the city’s DNA, a messy, ongoing element to life in Portland that can’t be reduced to a quirky joke on a T-shirt.


Proper attire
Except when it is!
While you’re in Portland, you’ll probably spot at least one incredibly cool-looking person wearing a shirt that reads ‘Wild Feminist’. This is the work of Portland women-owned, feminist-informed clothing line Wildfang. 
This is a company that recently came up with an inventive response to the uproar over Melania Trump heading out to immigrant detention centres for children clad in a jacket that read ‘I really don’t care. Do u?’ Wildfang retooled a military-inspired jacket so the back of it reads ‘I really care. Don’t u?’ 
Wildfang is arguably one of Portland’s most visible clothing companies, for its political stances as much as for its clothing (which is wonderful. They make a short-sleeved button-down in wacky prints) But it’s just one of many local clothing companies that make Portland a well-dressed city.
And while we’re on the subject of shopping, Skip downtown’s ‘Saturday Market’, which manages to be simultaneously underwhelming and kind of a madhouse. If you want locally designed clothing, you can get it from Portland lines such as Bridge & Burn and Poler, and if handicrafts are your thing, try Tender Loving Empire, Land Gallery and Crafty Wonderland.
If you’ve got a predilection for vintage, go digging for thrifted treasures at Magpie, which will impress even your coolest vintage connoisseur friend, and where I found a red cocktail dress from the ‘60s’ with an actual chiffon cape the last time I was in town.


Physical media lives
Powell’s City of Books is legendary for a reason, and it’s one of Portland’s touristy stops you absolutely must not skip. The small-press section is great for scoping out books from local indie publishers. The kids section is a massive treat for children and anyone who was once a child, the true crime section has rubberneckers covered, and the best-seller wall is always a fun glimpse into what the city’s reading and thinking about. 
And that’s not the only good news Portland has for physical media-loving luddites. Portland is home to a wide array of excellent, cheap movie theatres that almost all sell pizza. Living Room, down the street from Powell’s, has extremely comfy armchair-style seats and a full-service menu. And the Hollywood Theatre, the only theatre in Oregon equipped to show movies in 70mm, is kind of an institution. It’s where I’ve gone to see everything from Agnes Varda’s Faces Places to David Lynch’s Wild at Heart, with a guest appearance from Barry Gifford, whose novel the film is based on.
And if your film nostalgia extends to video stores, still-standing Movie Madness is also worth a visit. The platonic ideal of a friendly neighbourhood video store, this is where you can find an out-of-print edition of Silence of the Lambs, or pay a visit to a tiny collection of Hollywood treasures, including one of the prosthetic ears used in Blue Velvet.
That’s the thing about Portland, though: Portlanders know how to show up to a protest, but they also know how to have fun, and the more time you spend in the city the more you’ll see how closely linked these things really are. Portland’s politically minded scaffolding is what holds up the cute exterior, but fun, after all, can be its own form of resistance.
Once you understand that, it’s a lot harder to laugh at it. – The Seattle Times/TNS


Related Story