The Wandering Writer: A Tour through Inner Northeast Portland with Cheryl Strayed

Cheryl Strayed wants to show me the “dog bus” – but first we have to find it.

We walk along her quiet residential streets in Northeast Portland trying to track down the intriguing vehicle, my imagination running wild. Are we about to free a group of shackled dogs from animal control? Does Portland send its furry friends to school with their owners?

Eventually we locate our target on NE Halsey and 26th Street. The converted school bus is painted bright blue and splattered with paw prints and pup faces. The license plate says WAG. Strayed explains that Meg, a local woman, runs the quirky pet sitting service. It’s the kind of whimsical spectacle that you’d expect in a city that uses the slogan Keep Portland Weird – and it’s just enough off the beaten path that it feels like a bona fide glimpse into this tight-knit community where Strayed has landed.

She arrived here off the beaten path, too. Few folks today can claim that they literally walked their way to a new life, but Strayed is one of them. While hiking the Pacific Crest Trail at age 26, the subject of her bestselling-soon-to-be-Reese-Witherspoon-starring-book Wild, Strayed traversed the state of Oregon before winding up in Portland. It was 1995 and her finances were shockingly grim. Her life savings hovered around twenty cents.

“A friend of mine had a room for rent in her house and she said I could pay rent once I got a job,” Strayed says. “I didn’t know that I’d end up staying. I just knew that I needed to regroup and make some money.”

Her first modest moneymaking scheme was a yard sale where she offered up the few possessions she’d kept in storage, no more than could “fit in the back of a pickup truck:” thrift store purses, books and clothes, mostly. She mentioned to a friendly woman who bought a dress that she needed a job.

“She was a dancer,” Strayed says. “A modern dancer, not a stripper.”

It’s an understandable clarification. Portland residents often proclaim with varying degrees of pride or shame that the city has the most strip clubs per capita in the U.S., though some deep Googling leads me to believe the statistic is likely local legend.

Strayed’s new dancer friend also waited tables at the French restaurant L’Auberge, where Strayed soon started working, too. A Portland institution, it’s now closed, like many of Strayed’s old haunts from the 90s, including Satyricon, the rock club where Nirvana’s Kurt Cobain met wild child Courtney Love during a Dharma Bums concert.

This is back when a grimier Portland was ruled by street movements like the zine and punk rock scenes.

“All that stuff is gone,” Strayed says. “It’s been replaced with lovely things but things that are a little shinier and a little more polished.”

She’s fond of some of the improvements – she loves Stumptown Coffee and the food cart scene – but feels something has been lost as the city has gentrified. She admits she’s nostalgic for old Portland but also frustrated by an apparent psychological shift here.

“Maybe the biggest difference from when I first moved here is that nobody in Portland back then thought they were super cool because they lived here. There was Portland pride but it was coming from a more authentic internal place. Whereas now, everywhere I go, when I say I’m from Portland, people are like: Oooooh. I’ve heard it’s so great.”

While Portland is great, it has its problems, like anywhere. Strayed’s husband, Brian Lindstrom, currently has a documentary film out about an innocent forty-two year old man with schizophrenia who was beaten to death on the street in the now posh Pearl District. He died in police custody and there was a cover up surrounding his death.

“That’s Portland, too,” she says. “People forget that this city is complicated like every other city.”

Still, it’s clear Strayed’s heart is here. She’s traveled all over the world and Portland remains her favorite city, warm-hearted and community-focused. The inner northeast, along with the inner southeast, have always been her stomping grounds.

“I’m an east side person,” she proclaims with an authority that makes me need to know exactly what this self-designation means.

“East side isn’t as wealthy,” she explains. “You know that Everclear song, where he says: I’ll buy you a big house in the West Hills? Those are the West Hills of Portland. It’s swankier there. The east side has more working class vim, more of the people I think of as my tribe: writers, artists, filmmakers. It’s more funky.”

She’s generalizing, she acknowledges, like we all do, but it’s too late. I’ve already definitively proclaimed in my own head that, I too, am an east side person.

One of her favorite spots in the neighborhood appears filled with her tribe on this sunny Monday morning. Costello’s Travel Café on Broadway is a place with great pie and great coffee, where you’re offered a flag from some far-flung nation after ordering to signal not your allegiance but your waitress.

Over steaming pots of tea, I ask Strayed if she’s become a more public figure in the neighborhood after the success of Wild. She has, she says, and finds the change mostly flattering and surreal (see: nice lady stops her on the street to say she enjoyed the book) with an occasional smattering of unnerving and frustrating (see: someone tweets about her being at the grocery store at the exact moment she is in the grocery store).

One of the places where she’s surely most recognizable is at nearby Broadway Books, Strayed’s local independent bookseller. She worked out a deal with the owners to direct any requests from her website for signed copies to the store. This way, she can stop by on a leisurely afternoon to mark up her goods.

“When we pop by, they might have a few copies waiting,” she says.

It turns out the bookstore has many more than a few copies waiting for Strayed, 196 copies of the paperback version of Wild, to be exact, officially on sale the next day. Strayed promises to return soon to tackle the signings. For now we have a slightly more delicious quest in our sights in the form of the bakery across the street.

If Strayed ever feels nostalgic for old Portland, the Helen Bernhard Bakery might be a sugary cure. Established in 1924, long before Portland was cool, she calls the place “a real bakery.” To strengthen her case, Strayed offers up this incontrovertible evidence: you can get a glazed twist here.

She picks out two elaborately decorated cupcakes for her kids, one adorned with the face of a mischievous looking panda and the other a suspiciously happy cat. The grandmotherly cashier delicately places them in separate boxes and cautions us to be careful on our way home to prevent squashing the animals. It’s good advice that proves futile. An hour later we’ll present a mangled-face panda to her towheaded daughter who won’t mind in the slightest that her artful snack has been on the losing end of a heavy jostling.

Before we head back to Strayed’s house, though, we’ve got two more stops. The first is the straightforwardly named Great Wine Buys. The store is having a special where customers can order cases from a small vineyard in Italy.

“You can buy wine in the grocery stores in Oregon,” Strayed says, “but I prefer a bit more of an individual interaction.”

Our last stop is surprising after the row of independent enterprises we’ve been patronizing: Strayed leads me to the Lloyd Center Mall. More specifically, she takes me to its indoor ice rink.

“I had not been to a mall in, seriously, fifteen years, but my kids wanted to go ice skating one day and I wanted to pass that tradition on to them because I’m from Minnesota. And, lo and behold, there’s a rink in the middle of the mall.”

As the family-friendly scene unfolds, I ask Strayed if she’s staying in Portland for the foreseeable future.

Her answer is an emphatic yes. “This is home. I love Portland. I feel so lucky that I have access to an incredibly vibrant urban center – which is really where I see my life – and also the wild places that are so close, within thirty minutes. The coast, too. It’s just an hour and a half away and there you are on this incredibly rugged beach.”

Strayed spent her first few years questioning if she should stay. She kept asking: why am I here versus anywhere else? Am I only staying because I’m in love?

Then she and her husband moved to Syracuse, New York, so Strayed could get her MFA. It was only after leaving that she realized how much she missed her Portland community. They returned a few years later and she’s never looked back.

“For me,” Strayed says, “It’s always been important to leave a place. I think that’s a really important piece of growing up. It’s a conscious act. You’re not letting some river just take you. You’re actually directing yourself.”

And Portland is where you’ll find the grownup Cheryl Strayed, though, if you happen to run into her, maybe refrain from tweeting about it, okay?

About this Wandering Writer
Cheryl Strayed is the author of #1 New York Times bestseller WILD, the New York Times bestseller TINY BEAUTIFUL THINGS, and the novel TORCH. WILD was chosen by Oprah Winfrey as her first selection for Oprah’s Book Club 2.0 and optioned for film by Reese Witherspoon’s production company, Pacific Standard. WILD was selected as the winner of the Barnes & Noble Discover Award, an Oregon Book Award, a Pacific Northwest Booksellers Award, and a Midwest Booksellers Choice Award. Strayed’s writing has appeared in THE BEST AMERICAN ESSAYS, the New York Times Magazine, the Washington Post Magazine, Vogue, Allure, The Missouri Review, The Sun, The Rumpus–where she has written the popular “Dear Sugar” column since 2010–and elsewhere. Her books have been translated into twenty-eight languages around the world. She holds an MFA in fiction writing from Syracuse University and a bachelor’s degree from the University of Minnesota. She lives in Portland, Oregon with her husband and their two children.