The Wandering Writer: A Tour Through San Francisco’s Potrero Hill With Caroline Paul And Wendy MacNaughton

One afternoon in 2012, Caroline and Wendy’s cat slipped out the door and never returned. Until he did, that is – five weeks later, fat and happy, unperturbed by or unaware of the grief he’d caused his owners during his absence.

“It was a devastating experience,” says Caroline. “I’d had Tibby for 13 years and when he came back, I was like: I don’t know this cat. He can survive in the urban jungle. He has another life and I don’t know anything about it.”

Some pet owners might have chalked up Tibby’s temporary disappearance to one of life’s feline mysteries but Caroline decided she had to know where her kitty had been all those weeks. They knew Tibby was returning to wherever that was because even after he came home he wasn’t eating, yet the extra weight he’d gained on his little vacation stayed stubbornly put.

They decided to try and track him, first through a tiny GPS unit clipped to his collar, then with accompanying notes they hoped neighbors would read and respond to. When efforts that relied on technology and the kindness of strangers failed, Caroline turned to more offbeat strategies: a pet detective who didn’t understand what she wanted since her cat already been found, a woman who claimed she could teach people to communicate telepathically with their animals.

I asked if they thought it was simply that Tibby was getting better food elsewhere in their San Francisco neighborhood of Potrero Hill. Maybe the reason he had strayed was purely gastronomical.

“He was getting something he couldn’t get at home,” Wendy replied ominously.


Potrero is Spanish for “pasture” and that’s all Potrero Hill used to be: a one-stop grazing shop for sheep, goats and cows brought over by missionaries in the 1800s. Though it’s long abandoned its pastoral roots, the area has changed drastically even since Caroline arrived in 1992.

“It was always super industrial over here but the neighborhood was considered pretty unsafe in ’92,” she says. “Now it’s gentrified a ton and it’s so close to the freeway that the tech people from Palo Alto come live here.”

“The other thing as far as gentrification goes is that there is this Potrero Hill and then there’s another Potrero Hill,” Wendy says. “Right over that hill are some of the only public housing projects that remain in San Francisco. So you have, more towards the downtown facing side, some of the wealthiest tech people living in homes over there and then public housing over there. This is primarily white and that’s primarily African American. It’s completely segregated.”
Caroline and Wendy tell me all this as we make our way towards their favorite view in a city known for them. It’s on Arkansas Street and Caroline jogs ahead of us so we can snap photos of her in prime position.

“Keep going!” Wendy says. “More! More! More!” Caroline keeps shuffling away from us until it looks like she’s at the very edge of a cliff.

“Don’t I look like I’m at the end of the world?” she shouts.

Hilly San Francisco has such a plethora of spectacular backdrops that even the local public library has an amazing one. It just underwent a 5 million dollar renovation, expanding its second floor to maximize city views taken in through giant glass windows. A skylight pulls in natural light even on the greyest days and visitors in need of free Wi-Fi and a picturesque place to catch their breaths should add it to their to do lists.

As we walk towards 18th Street, the neighborhood’s main drag, Wendy tells me in a low voice that we’re passing one of the “mafia restaurants.”

“It’s the French restaurant mafia,” she clarifies. “They’ve opened one of every ethnicity of restaurant but it’s all French. So a Mexican restaurant. But it’s French Mexican. And the Italian restaurant. But it’s French Italian. And every time some other restaurant opens, they don’t last very long and then the French mafia ends up taking that space.”

“Is there some subterfuge there?” Caroline eggs her on, barely suppressing a grin.

“I think it’s just the same family who owns all the restaurants in Potrero Hill,” Wendy concedes. “But they really do.”

The couple is taking me to their neighborhood’s independent bookstore. It’s a place, Caroline says, “that by hook or by crook is going to survive, no matter the rough and tumble publishing industry.”

Christopher Books has had the same owner since 1992 and is full of the kind of carefully curated selections you’d expect at your local booksellers, including a whimsically decorated kids section that makes me wish I could fit into their nap-inducing miniature rocking chairs.

The store is quiet, like most of the streets we’ve walked since I arrived. I shrug this off as a lazy Monday phenomenon and Wendy raises an eyebrow. “Every day is kind of like this,” she says.
“Nobody walks,” Caroline tells me. “The hills here make it much less of a walking city. Until we started fostering a dog, we didn’t walk a lot, either. It’s embarrassing.”

Maybe the streets aren’t that crowded because everyone has taken up residence at our popular next stop: Farley’s. In the ’90s, the café scorned those who requested nonfat milk. Later it became the kind of place that outlawed cellphones and laptops. But all that’s changed.
“They have nonfat milk and wireless,” Caroline says. “They even have food.”

We grab three pine nut and goat cheese salads, me experiencing reverse sticker shock that they’re only $6 each, and grab seats outside near a tiny patch of park that has been inserted where once a few parking spots stood. The greenery is here because of SPUR, an urban planning initiative.

“They started Parking Day,” Wendy says. “On a certain day every year people take over parking spaces and set up parks. They grab a role of Astroturf and a beach blanket for their friends and some PBR. It’s really fun.” The space in front of Farley’s came out of the city offering businesses the opportunity to designate certain spaces permanently as parks.

We’re hoping to grab sweets at Baked, a dessert mecca opened in 2008, but sadly it’s closed on Mondays. I’m even more distressed by our bad luck when Caroline tells me about the homemade brownies stuffed with caramel and milk chocolate ROLOs.

“Caroline used to eat one a day,” Wendy says. Caroline, who has the lean physique of the former firefighter she is, nods sheepishly in agreement.

Caroline and Wendy have lived here for years (although she’s somewhat new to Potrero Hill, Wendy is a fifth generation San Franciscan) and know the neighborhood through and through. But it was only after Tibby disappeared that they started getting to know their actual neighbors.
“I’ve been here 20 years and I didn’t know people on either side of me,” Caroline says. “It’s common on the hill.” There’s no stoop sitting here and people just drive straight into their garages. But when Tibby went missing, the pair showered the neighborhood with flyers and went around asking: have you seen my cat?

“And of course everyone wants to talk to you about a missing cat,” Caroline says.

I ask if those relationships have been sustained and as if on cue a UPS driver leans out of his vehicle and addresses Wendy and Caroline by name, asking how their day is and mentioning a package he just dropped off with Wendy’s assistant. Caroline says the whole experience of tracking down Tibby made her aware of just how neighborly she was before. And she loves the little stories they’ve gathered along the way from other residents.

“I know this old guy who lived up the hill and he always worked in his garage so you’d see him if you parked your car on the street. And he’d say hi and I’d say hi. Turns out he’s been working on the hill his whole life. When I remodeled the house, he said: you’re the one doing the work on your place. How’s it going? And I said: I’m kind of worried about the foundation because it’s a 1926 house. And he said: oh no, you shouldn’t be worried. Your house was picked up in the 1950s from the other side of the neighborhood to make way for the freeway and plopped here so actually it’s a foundation from the ’50s.”

It’ the kind of information you only gather from chatting with your neighbors, if you’re the kind of people, as Wendy and Caroline are, who care about being part of a community – a community who eventually did help them find out where their wily cat had been hanging out for five weeks.

But that’s a whole other story…

About the Wandering Writers

Caroline Paul ( is the author of East Wind, Rain (HarperCollins, 2006) and Fighting Fire (St. Martin’s, 1999), and most recently, the book Lost Cat, A True Story of Love, Desperation & GPS Technology. Wendy MacNaughton’s ( illustrations have appeared in The New York Times, Wall Street Journal, and Print Magazine. She illustrated the book Lost Cat, A True Story of Love, Desperation & GPS Technology.

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.

The Wandering Writer: A Tour Through Brooklyn Heights, New York With Elisabeth Eaves

Elisabeth Eaves lives on Pineapple Street. Along with neighbors Cranberry and Orange, it’s one of only three fruit streets in Brooklyn. Eaves, a writer who has published on topics ranging from travel to politics to stripping, knows the accompanying local lore to explain its origin.

“Back when a lot of people were just moving to this neighborhood, it was dominated by old Dutch families,” she says. “The gentlemen of the neighborhood would affix their names to the streets. And there was a woman, a botanist and a horticulturalist, and she was annoyed that the men would just stick their names up on the street corners. She would take them down in the night and put up the names of plants. This went back and forth as kind of a cat and mouse battle for a while. And when the street names were finally grandfathered in by the city, she won, because she was the last person to stick up her names.”

This anonymous horticulturalist would no doubt be pleased that, more than a century later, Ms. Eaves and I are meeting for lunch at Iris Café. As if in deference to that earlier era, you’re not allowed to use computers or iPads at this restaurant that opened in 2009. Surrounded instead by folks engaged in the old-fashioned perusal of books and newspapers, we feast on delicious avocado sandwiches and talk about how Eaves, who was nomadic for years, finally settled in New York. She’s been here for four years and owns a small studio apartment. I ask if she’s found the geographic commitment difficult.

“It’s not as hard as I would have expected,” she says. “It’s partly because I love this city. As a traveler, I think many of us have a need for hyper-stimulation. I love big cities. Big, serious cities.” She doesn’t always find New York thrilling, the way she did when she first arrived. “But I still have days, and moments, where I’m like: wow.”

Eaves is, of course, one of many writers who’ve wound up in the area and she’s well aware of the borough’s literary legacy.

“As a writer, I am particularly conscious – not that I fetishize this stuff or think about it all the time – that there have been a lot of writers who lived in Brooklyn Heights,” she says. “It’s nice to know that things have been accomplished.”

Some of those things were accomplished at 142 Columbia Heights, Norman Mailer’s nautical-themed apartment. If we were lucky enough to get a glimpse of more than the exterior, a possibility when the place went on sale a few years ago, we’d see how the author installed crow’s nests, galley rooms and ladders, supposedly to overcome his fear of heights.

We do, however, spend some time taking in a foggy view of lower Manhattan by walking along the Brooklyn Heights Promenade, a popular 1/3-mile stretch along the Brooklyn-Queens Expressway. On nicer days, Eaves joins a cavalcade of joggers here who exercise to a traffic-laden soundtrack while winding towards or away from the iconic Brooklyn Bridge, the first steel-wire suspension bridge in the United States.

Not too far away we pass by another famous writer’s former homestead. Truman Capote’s brownstone, constructed at 70 Willow Place in the late 1800s, recently sold for $12 million. Maybe the buyer was a fan of “Breakfast at Tiffany’s,” which was written inside.

Thanks to long-gone reasonable real estate prices, Capote and Mailer no doubt had some version of the home offices that New York freelancers would kill for. But when you’re sharing a studio apartment, like Eaves and her husband do, it’s wise to find a laptop friendly café or two in the neighborhood. And Eaves has found just that in Vineapple Cafe on Pineapple Street, a joint run by a cadre of friendly, wrinkled-clothed college students.

The place has the laid-back feel of your college dormitory’s lounge, if that lounge served up Portland-based but New York favorite Stumptown coffee and Brooklyn’s Colson Patisserie baked goods, not to mention local wines and beers. When we enter, the roomy space is packed but quiet, some patrons happily sunk into plush couches, while a row of focused folks on laptops sit side by side at the bar like an unplanned ad for Apple products.

While we’re standing in line to order, a familiar face approaches. It’s Eaves’ husband, here to work for the afternoon. I ask Eaves if she likes having the flexibility of being a dual-freelancer couple or if she’d prefer a different arrangement.

“It would be easier financially if one of us had a steady gig but to me it’s normal now,” she says. “I’m kind of hooked on it. It would be really weird if either of us were suddenly like: no, I can’t go anywhere. Tomorrow we’re going to Vancouver for Christmas to see family. We can be very flexible. We can go as long as we want and bring work with us if we need to. And there have been a lot of work trips we’ve been able to put together and do together.”

Does she think she’s here for good?

“My fantasy is that I can keep the place we have now as a pied-à-terre,” she tells me. “If left totally to my own devices, there’s probably a good chance I’d just stay in New York.” But her husband is eager to move closer to family. The pair struck a bit of a deal when they first met: Eaves’ husband would move to Brooklyn for a stretch to be with her but he gets first dibs on the next city they relocate to.

Before we part ways, she takes me to one of the spots she might miss if she leaves New York. The sun has set by the time we enter Jack the Horse Tavern on Hicks and Cranberry Street. Eaves calls the big-windowed, brick-lined restaurant the best in Brooklyn Heights. If the happy hour cocktails are any indication, she’s onto something. We could continue our literary themed afternoon by ordering Hemingway daiquiris, but instead we both settle on gin infusions.

As we sip them, I ask Eaves about her varied career.

“My career path makes no logical sense,” she says. “You would never sit down at age 20 and say: I’m going to study international relations and then work as a stripper and then go backpacking and then have an office job.”

Despite her varied early years, Eaves knew she wanted to write but she didn’t know how to convert that desire into a career. It took a while to find her way into journalism, and along the way, she wrote about everything from moss sculptures to business. Now she’s tackling her first novel, like so many Brooklyn writers who preceded her – and like those who will, no doubt, flock here for future generations to come.

About the Wandering Writer:
Elisabeth Eaves is a writer and editor, born in Vancouver and living in New York City. Her first book, “Bare,” was about stripping, and her second book, “Wanderlust,” came out of a lifelong love of travel and trying to figure out why she felt so compelled to keep moving on. Her travel writing has also appeared in “Best American Travel Writing 2009,” “Best Women’s Travel Writing 2010,” and Lonely Planet’s “A Moveable Feast.” To read her stories, visit

[Photo Credits: Rachel Friedman]