Known as a vegan-friendly, coffee-obsessed, bike-riding haven, the Oregon city has only recently entered popular consciousness – mostly thanks to parodies of its hipsters. Jon Raymond explores the books that cast light on the best-kept secret of the Pacific Northwest

Only recently did the city of Portland, Oregon acquire the status of an Idea in the world. The Idea came about quickly, emerging from a pallid ether almost fully formed. A few years ago, it was: Portland, a place where it rains? And then, suddenly: Portland! A progressive Eden of tall bikes, home-roasted coffee, and art-damaged college grads. The Decemberists! Pork sandwiches! In a word: Portlandia. For those who’ve been here awhile the change can be disorienting. This always seemed like a place people came to disappear; now they come here to be discovered?

The strongest resident magic emanates through our great forest sorceress, Ursula K LeGuin

The books that embody the bygone city are predictably sparse, as the literature of Old Portland was produced piecemeal, without the benefit of cultural infrastructure of any kind. Among the extant texts are those of Stewart Holbrook, our great historian of the logging era, C E S Wood, an early anarchist, and the lately rediscovered Don Carpenter, a mid-century Portlander turned Bay Area beatnik, whose Hard Rain Falling depicts his youthful stomping grounds as a land of rough orphans, pool halls, and teen mayhem that could have easily landed in an early Gus Van Sant movie. His The Class of 49 is an elliptical, impressionistic group portrait of a graduating high school class in Portland – American Graffiti as penned by Sherwood Anderson – and his posthumously released Friday’s at Enrico’s summons a mid-60s community of aspiring writers struggling to find their voices in exile from California. Carpenter’s gritty, realist Portland is not all that far removed from Carver country (whose birthplace of Clatskanie, Oregon is only about an hour away), and finds update, arguably, in the works of Willy Vlautin, a bard of the North Portland horse track, and Mitchell Jackson, whose debut, The Residue Years, channels a jazzy, beatnik flow to show life on the African-American side of town (yes, Portlandia has many races).

Facebook Twitter Pinterest Hitting close to home ... Portlandia, the quintessential hipster parody. Photograph: Chris Hornbecker/IFC

But the old, hard-luck town always had a little magic to it, too, a beckoning, low-voltage promise. As a character in Raymond Carver’s story, Vitamins, mumbles at one point (obviously wishfully): “Maybe I should go to Portland. There must be something in Portland. Portland is on everybody’s mind these days. Portland is a drawing card. Portland this, Portland that. Portland’s as good a place as any. It’s all the same.” If Portland seemed to exist for a period as a kind of rumour of escape, a Plan B dream of refuge from the bright light of history, perhaps the novel that best captures that damaged enchantment is Geek Love, Katherine Dunn’s masterpiece from 1989. Conceived and written in Portland and partly taking place in Portland, the novel grandly imagines the adventures of a family of carnival freaks whose deformities are the result of eugenic experiments by the parents, Al and Crystal Binewski. Upon publication, the book achieved instant cult status among grunge-era romantics, and its totemic quality has only been strengthened by Dunn’s literary silence ever since. It’s possible that the same mossy, not-entirely-benign spirit that inspired Dunn’s tale of show business and self-mutilation speaks to Portlander Chuck Palahniuk and his acolytes as well.

But surely the strongest resident magic emanates through our great forest sorceress, Ursula K LeGuin. Recently in the news for her hair-raising speech at the National Book Awards defending literature against the bean-counters of Amazon, she has long been our Delphic Goddess in the woods – a feminist visionary whose prescient novels, stories, and poems have changed the shape of gender, class, time, and dragons in the collective imagination. In The Lathe of Heaven she summons the city itself, spinning a tale of a Portland man whose dreams shape reality, and the psychedelic consequences that result when that power is exploited by a nefarious doctor. What if one really could create one’s own reality, the book asks? What kind of hell would that be? What kind of insanity would it bring on?

Paired with Philip Dick’s Valis, another portrait of mystical mayhem in a West Coast countercultural milieu, The Lathe of Heaven deeply nails the psychic climate of the 70s bummer years, and the heartbreak that manifests when magical thinking goes truly awry. Perhaps it comes as no surprise to find that LeGuin is a California girl by birth. Just as Don Carpenter (and Richard Brautigan and Ken Kesey) dragged Oregon down into San Francisco, so she pulled Berkeley into Portland’s West Hills.

These days, Portland is a fairly well-established literary town, with a remarkably robust scene given its size. Current writers in residence include Cheryl Strayed, Karen Russell, Patrick DeWitt, Charles D’Ambrosio, Matthew Dickman, and many, many more. We’ve got Tin House Books, publishing excellent fiction to a worldwide audience, along with a bevy of other small presses; the mothership of all independent bookstores, Powell’s; and Literary Arts, our own combination of 826 Valencia, PEN foundation and 92Y [cultural institutions in San Francisco, across the USA, and New York, respectively] – and it is on the cusp of relaunching the city’s annual book festival, Wordstock. Its enough to make one wonder if the next artisanal DIY trend to emerge from Portlandia – after pickles, after knitting, after apple cider – might well be the old-fashioned art of writing on paper and binding it into books.