Portland may have a reputation for putting birds on things and performative quirkiness, but, as with most things, that’s not quite the whole story. That’s a good thing, and it should be the guiding principle for your next visit to the city.
Since the advent of a certain IFC show starring a member of Sleater-Kinney, Portland has been mythologized 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.
Add in its laid-back pace of life, its slowly disappearing dive bars, its casually gorgeous riverfront bike trail and its transit-friendly navigability, and 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 while drinking a cold brew in a flannel after hitting up the weed store but before going to the vegan strip club, be my guest. You won’t need my help finding those things, and they 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.
A culture of resistance
Portland is a beautiful city bisected by the Willamette River. It’s 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 2015 (savvy demonstrators rappelled gracefully off the St. Johns Bridge) to vaccines (see: the city’s recent measles outbreak).
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 publicized was the peaceful rally beforehand, and that in the same week, one of the protest’s organizing 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.
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” across the chest. 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 centers for children clad in a jacket that read “I really don’t care. Do u?” Wildfang retooled a military-inspired jacket from their own line so the back of it reads “I really care. Don’t u?” With all proceeds from the $89 jacket going to the Refugee and Immigrant Center for Education and Legal Services (RAICES), a Texas-based organization that provides free or low-cost legal assistance to immigrant children and families, the first 100 coats sold out within an hour, and three days after the initial run was announced, Wildfang had raised about $250,000 for RAICES, a company representative told Teen Vogue.
Wildfang is arguably one of Portland’s most visible clothing companies, for its political stances as much as for its clothing. 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 (1122 S.W. Morrison St.) and Poler (413 S.W. 10th St.), and if handicrafts are your thing (or you really need a Nikki McClure print), try Tender Loving Empire, Land Gallery and Crafty Wonderland.
If you’ve got a predilection for vintage, go digging for thrifted treasures at Magpie (1960 S.E. Hawthorne) where I found a red cocktail dress from the ’60s with an actual chiffon cape the last time I was in town. It set me back all of $18.
Physical media lives
Powell’s City of Books (1005 W. Burnside St.) 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 and YA sections are 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. (Hate crowds? Visit Powell’s second, smaller store in the Hawthorne District.)
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 theaters that almost all sell pizza and beer (the Laurelhurst Theater, even has mimosas). 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 theater 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 neighborhood 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.
The great nearby
One of the best things about Portland is that you can actually go on a full-blown hike without leaving the city. Northwest Portland’s Forest Park is a sprawling, urban-adjacent gem. In Southeast Portland, smaller but no less impressive Mount Tabor is home to an extinct volcano, huge cedars, oddly grand outdoor reservoirs and, at the summit, a beautiful view of the city. If you’re in the mood for a bike ride, the Springwater Trail, along the Willamette in the Sellwood neighborhood, is the most picturesque stretch I’ve ever ridden – you’ll cruise down a flat, paved trail that passes a wildlife refuge and an amusement park.
Want to tack another destination onto your Portland trip? The coast is an easy drive, if you’re in the mood to Instagram Haystack Rock (as is customary). But if you make it that far, you should consider driving across the 4-mile Astoria-Megler Bridge between Astoria and southwest Washington. Across the river, in tiny Seaview, you’ll find my favorite vacation spot anywhere: the Sou’wester Lodge.
All twinkle lights, pine needles, sea air and vintage chrome, the Sou’wester has easy access to miles of trail along the beach, plus an assortment of accommodations, including restored travel trailers (Potato Bug is my favorite!), old-fashioned vacation cabins and a jaunty lodge.
Doughnuts and day-drinking
I know, I know: You feel obligated to go to Voodoo Doughnut, alleged fried-dough icon of Portland. But unless you want to wait in line for a dry-in-the-middle doughnut coated in gluey layers of Day-Glo frosting and novelty toppings like (stale) Froot Loops, don’t.
Get a real treat at Blue Star, which makes dense, chewy, flavor-saturated doughnuts. The result is sweet – doughnuts should be sweet – but not so sweet it’ll make your teeth hurt. The buttermilk old-fashioned is my favorite – a meal in itself that tastes like spun butter and sunshine and pairs perfectly with black coffee for a quick breakfast. And if you’re a nostalgic East Coast transplant, you might also appreciate Sesame Donuts, which was originally a Dunkin’ Donuts franchise, and makes the closest thing to a “regular coffee” you can find in the Pacific Northwest.
For fancier meals, Le Pigeon is where I took my French cooking-expert aunt when she visited for French-inspired Northwest fare. Little Bird Bistro is another good option for a Parisian meal that’s closer to the traditional thing. And I can say nothing but good things about the Ace Hotel’s restaurant, Clyde Common, where I have passed many a pleasant evening over honey-butter popcorn and cocktails with friends. For breakfast (or any meal, really) head to Lauretta Jean’s for coffee and pie that’ll satisfy your inner Dale Cooper.
In the afternoon, Portland’s summertime back patios become its oases. I recommend the ones at Night Light Lounge for chill neighborhood bar vibes or brunch (you can almost always get a table), Aalto Lounge and Rontoms for eavesdropping on extremely hip Tinder dates and A-plus people-watching, and the Space Room Lounge for when you really just want a dive and a picnic table.
But the piece de resistance of Portland’s outdoor drinking options can be found at Revolution Hall , a converted high school in Southeast Portland that now operates as a venue for music and comedy, and has the nicest rooftop bar I have ever been to, with a 360-degree view of the city, and an air of quiet blasphemy (you’re drinking at school!).
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.