The “idea” of Portland only entered the popular imagination in recent years, chiefly thanks to the comedy TV show Portlandia, as Jon Raymond wrote recently. But this city, known as a haven for vegans, iced latte lovers (yes, flat white fever hasn’t conquered America – yet), beards, fixed-gear bike worshippers and any other hipster stereotype you want to invoke, is more interesting and surprising than this suggests.

Whether you’re planning a trip to this Pacific Northwest city or you want to find out more about it through its literature, you’re in for a treat, thanks to a collective brainstorming we did with our readers. Here are the top picks. Is your favourite missing? Do add it in the comments.

1. Lean on Pete by Willy Vlautin (2010)

Willy Vlautin has published four novels, all of which were recommended as “superb” Portland reads by mikeollier, and all of which have been praised as portraits of bleak contemporary America. His third book, Lean on Pete, tells the story of a teenager who lives in a race track in the city. His latest, The Free (2014), was praised in a Guardian review:

“It is love, in all-American, over-salted, extra-large portions, that makes The Free original and compelling. [...] Freddie and particularly Pauline waddle triumphantly out of their heaps of shopping and stacks of bills as convincing, heroic people, and provide ample shoulders over which to peek at Vlautin’s blasted vision of the US.”

Not all of his works are strictly Portland, but “many of the stories centre around the Pacific Northwest and a broader theme of societal marginality in the new west,” added tproland. Vlautin wears a second hat as the frontman of alternative country band Richmond Fontaine, which mikeollier pointed out to us. Many of his lyrics also touch on the city and region. Case in point:

In quotes from the book:

I drifted and I drifted, ended up in Wyoming/I got so broke I sold my car.

Look, here’s a piece of advice. What you do is you think about the life you want, you think about it in your head. Make it a place where you want to be: a ranch, a beach house, a penthouse on the top of a skyscraper. It doesn’t matter what it is, but a place that you can hide in. When things get rough, go there. – from The Motel Life

2. Fugitives and Refugees: A Walk in Portland, Oregon by Chuck Palahniuk (2003)

Chuck Palahniuk is not for everyone – or for every stomach, should I say. But if you’re a fan of the Fight Club author and Portland native, you can’t miss his travel guide of sorts. Dan Glaister wrote on the Guardian:

Fugitives And Refugees is that most quaint of things, a travel book - but it’s not quite the book his publishers hoped for. Instead, it is a series of essays, postcards and ruminations on the underbelly of his home town, Portland. Yet beneath the profanities and the glitz of his new book [...] there is a calm, spiritual Palahniuk fighting to get out. This side also struggles out in conversation, sometimes in the most unexpected of ways.

Underground tunnels, strange customs, a self-cleaning house, sex clubs, local vocabulary, anecdotes and lots of strange facts like where Palahniuk’s tonsils currently rest await you. Recommended by rustybeancake and smudger1.

In quotes from the book:

Katherine’s theory is that everyone looking to make a new life migrates west, across America to the Pacific Ocean. Once there, the cheapest city they can live in is Portland. This gives us the most cracked of crackpots. The misfits among misfits. ‘We just accumulate more and more strange people’ she says. ‘All we are are the fugitives and refugees.’

3. Jumptown: The golden years of Portland jazz, 1942-1957 by Robert Dietsche (2005)

rdb1 pointed us to this nonfiction mix of politics, music and history, which explains the golden musical decade that followed the second world war, in which jazz thrived in the Oregonian city – “not all of it is that evocative but if you have an interest in jazz, Portland, and black removal (aka urban renewal) I recommend it”.

In quotes from the book:

Action central was Williams Avenue, an entertainment strip lined with hot spots where you could find jazz twenty-four hours a day. What is now the Rose Quarter used to have a lot of other names. Any cabby worth his fare would have known that Black Broadway, the other side, colored town, all meant the same thing: the Avenue, namely Williams Avenue. Fifty years ago you could stand in the middle of the Avenue (where the Blazers play basketball today) and look up Williams past the chilli parlors, past the barbecue joints, the beauty salons, all the way to Broadway, and see hundreds of people dressed up as if they were going to a fashion show. It could be four in the morning. It didn’t matter; this was one of those ‘streets that never sleep’.

4. Mala Noche by Walt Curtis (1977)

“No mention of Walt Curtis? Without his Mala Noche, you might never well ever have heard of Gus Van Sant,” said Marzek. This Portland story might be well-known for the filmmaker’s adaptation (another famous Portlander, incidentally), which pretty much kickstarted the director’s career, but Curtis’s autobiographical novel is as gripping a depiction of the city in the 70s. In it, Curtis, considered the city’s street poet and often associated to the Beat authors, explained his relationships with Latino teenagers in the city’s Little Mexico neighbourhood. alonk said:

Mala Noche, also one of Van Sant’s first films, captures well 1970s Portland, before Skid Row residents were evicted and the area was turned into “The Pearl” and homeless shelters and cheap hotels became stores selling expensive junk. As a native of Jerusalem and a resident of Portland for many years (with stays in London, Eugene, Davis and Berkeley) there is much to recommend the city, the mountains, trees, and many progressive minded people.

In quotes from the book:

I don’t want to interfere with their lives. A gringo like me has an easy life. A privileged life. And just because I see someone attractive like Johnny it doesn’t mean I should be able to have him, to buy him or whatever, just because he’s hungry and on the street. Desperate, good-looking. That wasn’t my intention exactly, but it could be misunderstood that way.

5. The Girl Who Fell From the Sky by Heidi W Durrow (2010)

In this novel, a mixed-race girl from Chicago is forced to move to Portland after suffering a family tragedy, with her African-American grandmother as her guardian, and with a mostly black neighbourhood as her new home. Mirroring Durrow’s own experiences of displacement and race, it was reviewed in the New York Times: “It’s when it approaches the questions of identity and community subtly and indirectly that The Girl Who Fell From the Sky can actually fly,” wrote the reviewer. Recommended by bevpdx.

In quotes from the book:

A woman made of parts is a dangerous thing. You never know when she’ll throw away a piece you may need.

Math can explain the reason there’s one out of four chance that I’d have blue eyes. But it doesn’t explain why me.

6. Wildwood by Colin Meloy and Carson Ellis (2011)

Scott Duncan strongly recommended this children’s book by Colin Meloy, The Decemberists’s singer and songwriter, and artist Carson Ellis, his partner:

Fantastic books for older kids (my daughter is 12 and we read them aloud). Wildwood is a magical land across the river from Portland that seems stuck in the late 19th century, with some extra magic thrown in. On one level, Meloy is writing a gentle satire of beardy hipsters. But on most levels, Wildwood is a great adventure story featuring cool kids saving the world.

An American Narnia, according to the Guardian review by Patrick Ness.

In quotes from the book:

My dear Prue, we are the inheritors of a wonderful world, a beautiful world, full of life and mystery, goodness and pain. But likewise are we the children of an indifferent universe. We break our own hearts imposing our moral order on what is, by nature, a wide web of chaos. It is a hopeless task.

7. Shot in the Heart by Mikal Gilmore (1995)

Arnold Ward recommended this memoir written by Rolling Stone journalist Mikal Gilmore, describing it as a “harrowing tale of growing up in a dysfunctional Portland family, which included his notorious brother Gary Gilmore whose insistence on being executed by firing squad reignited the death penalty in America.” Indeed, Gary Gilmore was the murderer depicted in Normal Mailer’s The Executioner’s Song, who campaigned for his own death. But he wasn’t the only member of a stunningly dysfunctional family.

In quotes from the book:

That attitude of smugness held sway in Portland for several generations, keeping the place hidebound and insular. Consequently, Portland was largely unprepared for the influx of population.

8. Night Dogs by Kent Anderson (1996)

This list wouldn’t be complete with a police tale – and the novel Night Dogs, recommended by ymgmat18, is a “long, fiercely authentic and deeply disturbing novel about police officers serving as an “army of occupation” in America’s slums,” in Portland’s high-crime North Precinct, according to the Los Angeles Times.

In quotes from the book:

Nobody has any rights unless they’ve got a machine gun.

9. I Loved You More by Tom Spanbauer (2014)

Spanbauer is one of those essential Portland literary figures – the heart of the city’s literary world, according to many local authors. (Do check his conversation with Palahniuk on The Believer magazine.) This novel, his latest, features the city as the setting – together with New York City – of a love triangle that spans a decade and includes university relationships, literary conversations, confused male friendships and reflections on age. It was recommended by johnmcrae.

Extra notes and literary facts

• It’s worth mentioning the children’s fiction of Beverly Cleary (creator of characters such as Ramona Quimby) which, as countzero1 pointed out, is the entry for many readers into the city. Here’s a talk The Atlantic had with her four years ago (when she was 95!), a New York Times profile about her ageless appeal and an essay about her published on the Oregon Quarterly.
• As countzero1 pointed out (he was told it by a couple, when visiting in 1982), the infamous Vesuvio Café in San Francisco, which is right in front of the City Lights bookstore (both of Beat Generation fame), has a scrawl on the rim of the entrance, that reads: “We are itching to get away from Portland Oregon”. You can read more about it – and about the history of the place – here and here.
• For football/soccer nerds, Michael Orr’s history of the sport in Portland sounds like a great read – find out more on Brenton’s comment.
• And a final anecdote: Gary Snyder, Philip Whalen and Lew Welch were roommates at the city’s Reed College. “One of the most significant student pads in the history of American poetry, surely?” asked BillyMills – rightly so, in our opinion.