Portland, Oregon has many sides. Tom Austin favors its idiosyncratic indie scene, where fair-trade cafés and strip clubs draw the same clientele, ethics are in, and music fuels the urban engine.

By Tom Austin
April 03, 2009
João Canziani Melissa Thaw, skateboarder by night, in Portland's Burnside Skate Park, built by boarders.
João Canziani

A swallow flutters about the rafters of the Oregon Zoo band shell and out over a vast green meadow as Thomas M. Lauderdale—the pianist and artistic director of Pink Martini, everyone's favorite postmodern cocktail-lounge orchestra—strolls through a gathering of his tribe and distractedly chews on a slice of pizza. This being the People's Republic of Oregon, the 3,500 or so picnicking audience members include Birkenstock families with Live Green, Live Well stickers on their strollers, lesbian riot-grrrl collectives, cheerful Marxists, and the requisite too-camp-to-live fan pool of the orchestra's neoclassical-goes-international oeuvre: reinterpreted Carmen Miranda numbers; compositions performed in Arabic, Japanese, and 10 other languages; and "The Gardens of Sampson & Beasley," a lilting ode to a wistful Portland afternoon. In an offhand way, Pink Martini, which played Carnegie Hall this summer, concocts a glossy-postcard vision of the city as an eternal carnival of whimsy: the band's brilliantly evocative concerts, with the musicians dressed for cocktails, are about longing—Portland as it ought to be, not as it is.

Then again, Portland is a perverse and obstinate place, adept at resisting the imposition of sentimentality and outside values: this is the city, after all, where a brand-spanking-new Starbucks was firebombed in 2004, shortly before its opening. The citizenry believe in throwing it all out there—rampant political correctness, vice, whatever else might be handy—without sweating the distinctions. To "shamelessly promote" the band's third album, Hey Eugene!, Lauderdale, a self-styled musical archaeologist who serves as the unofficial mayor of bohemian Portland (and toys with the idea of running for the real mayor's office every few years), has his 12-year-old nephew come onstage in a Pink Martini bomber-style jacket inspired by one sold at the circa-1954 Mary's Club, a downtown institution and Portland's first topless bar. This is a pure Portland moment, a long way from the mythological terrain of Cole Porter's New York or even Louis Armstrong's New Orleans.

Alternative Portland is a peculiar utopia that believes in both unbridled sensuality and the notion that doing good actually makes people happy. This may be the most right-thinking community in the United States, brimming with green buildings, biodynamic wine, light-rail systems, homeless programs, fair-trade restaurants like the Proper Eats Market & Café ("organic, local, proper!"), bicycle-commuter lanes, solar-powered parking meters, and such resolutely moral establishments as the Red & Black Café, a collectively run coffeehouse lousy with laptop beatniks conforming in their devotion to the fight-the-power manifestos the management has posted on placards: We Want to be an Example of an Ethical, Nonhierarchial, Worker-Run Operation. The more heedless this country becomes, the more thoughtful Portland tries to be, and the city invariably makes visitors wish their own hometown could be a little nicer.

Even the layout of Portland, founded in 1851 as a shipping hub and logging town hugging the banks of the Willamette River, was intended by the city fathers to be intelligent and vaguely nonhierarchical. The best feature of the city is its classic American urbanism, pockets of bungalows and Victorian houses with howdy-neighbor front porches close to small historic movie theaters, shops, and taverns. In the early 1940's, a grandiose and half-deranged proposal by Robert Moses to carve up Portland with freeways led to a neighborhoods-above-all movement, and the movement prevailed. Today, each little enclave is a small, restful village that's handy to the big bad fray of downtown.

Burnside Street and the Willamette River form a cross that divides the city into quadrants: historically, much of the district known as Northeast was African-American, though that has been changing over the past 15 years in areas like North Mississippi and Northeast Alberta, as the ballyhooed creative class descends on the city; Southeast encompasses the let's-do-the-1968-time-warp Hawthorne neighborhood (head shops, socialists working the streets), Reed College, and the pure Leave It to Beaver charm of the Belmont district. In Northwest, the city becomes more urban and grittier—Chinatown, Old Town—then softens into the monied calm of Nob Hill even farther north and west. Southwest begins as the rough-and-ready nightclub zone around Mary's; then the tone changes with downtown office and government buildings and the cultural district with the Portland Art Museum, Portland State University, and the elm-lined South Park Blocks, a narrow swath of green that's home to the popular Wednesday farmer's market.

Although this city of 538,000 has a knack for inspiring visitors to rise to its level of resolute consciousness, it is also home to swingers' clubs; the tattooed-up-the-wazoo punk stars of the Suicide Girls' alt-porn film studio; several entirely aboveground gay bathhouses; and what must be more all-nude strip joints per capita than any other city in the country. The latter tend to be beat-up neighborhood dumps rather than silicone glitz palaces; oddly enough, reasonable-looking young couples in the crowd are not an uncommon sight. Strip bars are as ordinary as the city's ubiquitous microbrew pubs, which are full of evolved frat boys in SNOB (Supporter of Native Oregon Beer) T-shirts. Mary's, which went all-nude years ago to compete, is the most beloved operation, adorned with vintage glossies of exotic dancers and a beautiful WPA-style mural of heroic, profoundly muscled dockworkers. Courtney Love started out here, and when the 90-year-old owner Roy Keller died last summer—his daughter Vicki runs the place now—the Oregonian ran a story that lionized him as an all-around great guy and visionary of the industry: "...a man who hired gays, African-Americans, transvestites, and snake handlers...." At times, even the voice of mainstream Portland can get a little too dreamy.

Lauderdale lives and works in a converted commercial building close to Mary's. Pink Martini's offices and rehearsal studios are on the ground floor, and their parties—attended by the likes of former Interview publisher Paige Powell, a Portland native who is devoted to causes like the Wildlife Rehab Center of the North Coast—tend to spill out into the street and mix with the after-hours set lurking around Voodoo Doughnut, last call for Red Bull doughnuts and "voodoo" weddings: $25 Intentional Commitment affairs as well as entirely legal ceremonies with doughnuts and coffee. After midnight, Voodoo Doughnut is always full of local musicians, and music, often driven by neopsychedelia conceits and smart lyrics, is the engine that drives this city: Portland has long since surpassed grunge-era Seattle as an indie cultural capital. One young alt-rock snot dismisses Portland as a "retirement home for indie rockers," though the local all-stars include members of Modest Mouse, Death Cab for Cutie, the Shins, the Decemberists, Spoon, and the Thermals. (Gino Vannelli, glam god of the 1980's, also lives in town for some reason.) Portland has even entered the Great American Songbook: in "I Will Buy You a New Life," Art Alexakis of Everclear promises to give his beloved a home in the West Hills, the Portland equivalent of Beverly Hills.

Rich or poor, they all come to Portland for the quality of life. In the past few years, Portland has become a metaphor for enlightened humanism and progressive government, a little pocket of Sweden in the States. Richard Florida's The Rise of the Creative Class: And How It's Transforming Work, Leisure, Community, and Everyday Life has become a bible of development for forward-thinking city planners and politicians, and every city is trying to lure the eminently employable post-yuppie Information Technology nomads who can revitalize a moribund downtown almost overnight. Portland is a city of youth and intelligence, full of microbrew-chugging tech nerds from the campuses of such higher-learning institutions as Intel, Nike, and Adidas. The new people in town are fleeing mainstream America, especially the deracinated, let's-grab-a-bite-at-the-multiplex life of the soul-crushing suburbs.

Portland could be this country's largest European-style city. It has more green space than any other comparably sized American metropolis: in the hills to the west is the 130-acre Washington Park—home to the Oregon Zoo, the International Rose Test Garden, and the exquisitely serene Japanese Garden—plus the 70 miles of trails in Forest Park, the most extensive urban wilderness in America. Portland also remains a capital of environmentally responsible design, as reflected by Holst Architecture's revolutionary Ecotrust Building and Boora's Adidas Village. The city is in the forefront of the national movement toward locally grown organic produce: sustainable-food champions Plate & Pitchfork stage elaborate outdoor dinners at local farms, and such stalwarts as Park Kitchen, Paley's Place, and Higgins Restaurant & Bar have all won or been nominated for James Beard awards. Greg Higgins can whip up a masterful seared Oregon albacore tuna with red wine ragout and knows every corner of the farmers' market, where he combs through free samples of sweet, heart-shaped Rainier cherries. Nearby are fragrant loaves of Pearl Bakery bread and lamb-on-pita sandwiches from the Tastebud Farms mobile grill. Portland is a daily lesson in how simple, everyday food should taste.

Like Charleston, Portland is one of the most polite and civilized American cities imaginable. The audiences at the Chamber Music Northwest festival know when and when not to applaud, and even at rock concerts fans actually listen to the music: during a performance by the withered rockers the Bottle Rockets, at the Crystal Ballroom, the rapt crowd resembled Easter Island megaliths with a penchant for beer. America has become a lonesome country, full of isolation and distrust, but strangers actually talk to one another in Portland, and more. One summer afternoon on Northwest 23rd Street, the local equivalent of Rodeo Drive, a homeless woman suddenly began pulling at her face and screaming about dry skin: rather than turn away, two Prada warriors who were passing by rushed over and gave her some moisturizer.

At certain moments, it's very easy to forget that Portland began in darkness. Throughout the late 1800's, during the reign of the notorious kingpin Joseph "Bunco" Kelly, unwary customers in Chinatown gambling dens would be drugged and then carted through "Shanghai tunnels" (tourists can now visit a section of one of these legendary tunnels below Hobo's Restaurant & Lounge) to ships tied up at the Willamette River, then sold to sea captains as indentured sailors. During Prohibition, an era when the Ku Klux Klan put its own mayoral candidate in office, the city moved into smuggling Canadian whisky, then into brothels. Until the late fifties—when Bobby Kennedy and the Senate Rackets Committee dragged assorted politicians and gangsters to Washington, D.C., for televised hearings—it was a dirty little town, a national code word for sin and fun. Tempest Storm was running her own strip show at the Capitol Theater, Justice William O. Douglas and a local B-girl named Little Rusty were taking in an unknown Sammy Davis Jr. at the Clover Room, and Bugsy Siegel contemplated opening a casino in the northwest part of town on Sauvie Island, now home to a nude beach and organic farms. These days, save for a few sputtering neon signs trumpeting the charms of chop suey and cocktails, the mood of even Chinatown is gone, though there's a whisper of the old Portland after dark at places like the Alibi. Downtown property is too valuable to serve as mere atmosphere: the fancy Governor Hotel was derelict when native son Gus Van Sant shot parts of My Own Private Idaho there in the early 1990's. Now, the lobby is connected to—what else?—a Starbucks.

The Pearl District, west of Chinatown, was a seedy, highly cinematic neighborhood not that long ago, the setting for much of Van Sant's Drugstore Cowboy, his 1989 elegy to lost squalor. But now it's the pride and joy of official Portland: in 2001, to spur development, the government installed a Czech-made streetcar system linking downtown to the fringes of the Pearl. The North Pearl has become an even more alienating and scary version of New York's SoHo, with the streetcars silently gliding past Liveinthepearl.com realtor signs in a Soylent Green kind of way. Powell's City of Books, widely regarded as America's best independent bookstore, anchors the more seasoned stretches of the Pearl, close to the Bettie Ford Lounge, the new Ace Hotel, gay bars, assorted flophouses, and the hale and hearty Jake's Famous Crawfish Restaurant. In the café at Powell's, Mike Richardson of Dark Horse Comics, which published Frank Miller's Sin City, is chatting about Tonya Harding and selling comics to the followers of Bhagwan Rajneesh, whose rogue-ashram wreaked havoc 22 years ago in Antelope, Oregon.

Like everyone else in Portland, Richardson is sunny as all get-out, pointing outside the café windows to a Brave New Urbanism scene that could have been choreographed by an exceptionally hip Chamber of Commerce: the requisite Wavy Gravy wannabes twirling around as if it were still the summer of love in Haight-Ashbury; an apparently homeless young professional gone astray, lying with his purple hair splayed out on the sidewalk, nodding politely at gaping tourists while he reads Morgan Spurlock's Don't Eat This Book: Fast Food and the Supersizing of America; an earnest businessman on a high-tech tricycle pedaling past hardwired nut jobs, meth heads, and one schlub in ordinary street clothes whose face is completely tattooed in a checkerboard pattern. This human comedy resembles a curious laboratory experiment—it would have gotten B. F. Skinner going in all kinds of different directions—but perhaps happiness can be as effectively engineered as a streetcar system, since everyone in town, as Richardson points out, "just can't stop smiling."

Portland grants the gift of hope: the Holy Grail of freedom, the joy to be found in chance and opportunity are the promises this country was founded on, and more American cities could stand to loosen up and let the possibilities of life unfold. Across the street from Powell's is a stack of 20 or so customized children's bicycles chained to a pole: on Sunday nights, the Zoo Bombers—just one of the local bicycle tribes (two others feature convoys of nude riders and daredevil jousters)—meet at Rocco's Pizza, then ride down the hill from the zoo on busy thoroughfares, dodging cops and cars along the way. Portland changes people: within a few days, I found myself dancing in mosh pits at punk clubs, and one loopy evening, I just narrowly missed the chance to become a middle-aged Zoo Bomber.

Any American Eden is a fragile proposition and Portland is consciously trying not to repeat the urban-planning mistakes made by its traffic-ridden neighbor Seattle. But the money is pouring in at every level, and tract-house developers are continually making assaults on the Urban Growth Boundary, which rings Portland and was designed to contain suburban sprawl. One of the best things about this city is how quickly visitors can get out of town: true bucolic landscapes—right down to the inevitable pickups bearing Confederate flags—commence just past the city limits, and within an hour or two, it's possible to be surfing at Cannon Beach or skiing—even in summer—on Mount Hood, the magnificent dormant volcano that looms over the town.

For aspiring artists and kids just out of college, Portland is still a refuge for the DIY (Do-It-Yourself) indie dream that New York, San Francisco, and Seattle afforded 20 years ago: inexpensive rental apartments, cheap bars, and the chance to jump-start your ambitions with a post-punk band, performance-art collective, experimental film, or a line of clothes that can be sold in local boutiques like Magpie. Failing that, they can hang out at the Black Rose Collective Bookstore & Community Resource Center in the North Mississippi section of town, a fantastic power-to-the-people commune-thrift operation (everything in the shop is free) with an anarchist bent: "Not one yuppie vehicle should be safe...."

The poor and just plain feckless can saunter through all the free gallery openings, concerts, and street fairs, brace themselves for four-inch distended earlobes at the "painfully friendly" Robot Piercing, catch the raucous MarchFourth Marching Band in their flapper costumes and stilt-walking ensembles at Doug Fir Lounge, grab a beer and veggie dog at Acme, or go to the Press Club for some punk history—Dave Allen from Gang of Four, the seminal British punk band, worked at Intel for a time and spins here occasionally. The idle can marvel at the sheer grace of skateboarders at the Burnside Skateboard Park, built entirely by boarders, or shop at the funky boutiques along Northeast Alberta Street. (One morning, the most stylish girl on the street turned out to be a hobo who hops freight trains around the country.) The fashion-forward—pierced and fierce pretenders to the throne of Kurt Cobain heroin immortality, the neo-mods, the gloom- and-doom girls working an emo-lite look somewhere between Emily the Strange and Wednesday Addams—can simply join the Quadrophenia-revisited crowd at Pioneer Courthouse Square, which also happens to be a prime milling area for tourists. Among the kids, the scene is as arcane and calibrated as life among the style tribes of Tokyo; it's enough just to be cool in Portland, and that energy percolates throughout the city.

Courtney Taylor-Taylor of the Dandy Warhols climbed out of the local grit ghetto to a house in the West Hills with songs like "Not if You Were the Last Junkie on Earth" and "Bohemian Like You," a satire of the Pacific Northwest poverty-equals- integrity aesthetic that wound up on a General Motors commercial. The symbol of his DIY-dream-come-true is the Odditorium, a former machine shop north of the Pearl that he transformed into a psychedelic playhouse for sort-of grown-ups, equipped with motorcycles, pool tables, murals of the Sahara desert, medieval-style doors, Victorian chairs, a louche little bar, and a recording space for the band. The Eagles of Portland are living it up at the Hotel California, and at a barbecue one evening—attended by the usual hangers-on and, naturally, a stripper ("I like Portland because it's so clean," she tells me)—the guests debate the grassroots-gone-mainstream KEEP PORTLAND WEIRD bumper sticker campaign. Portland's marketing onslaught began a few years ago, some time after the similarly lame but lasting effort mounted by Austin, Texas (KEEP AUSTIN WEIRD), and now the Portland stickers are turning up everywhere, even in the city's official media kits. To Taylor-Taylor, a "keep Portland weird" groundswell is "precisely the kind of thing that guarantees Portland won't stay weird."

Portland is still plenty weird—on the way back to my hotel on the evening of the barbecue, a cab driver affably talked about being the reincarnation of Amun-Ra, a destiny that inevitably inspired the Ammon-Ra Web site, but what is really remarkable is the openness, the willingness to trust in goodwill.

In Portland, anyone who walks into Alma Chocolate, specializing in organic, fair-trade chocolate molded into religious icons, might run into Chuck Palahniuk, the exceptionally fit forty-something author of the novel Fight Club. The exquisitely well mannered Palahniuk is also the author of the new Rant: An Oral Biography of Buster Casey and Fugitives and Refugees: A Walk in Portland, Oregon, the definitive guide to such singularities as the drag institution Darcelle XV, the Vacuum Cleaner Museum, the Van Calvin Mannequin Museum, and the 24 Hour Church of Elvis. Palahniuk moved to Portland in 1980, when it was still a blue-collar town, and the more recent history of his beloved dirty little city is an intensely personal affair: "When I think back and get nostalgic, it's hard to tell if I'm missing the grungy old days of Portland, or being twenty-two and immortal."

When to Go

Summer and early fall have the best weather, though Portland has relatively mild winters and only 36 inches of rain per year.

Getting There

Portland is served by most major carriers. The Airport MAX line (trimet.org/max), delivers travelers from the airport to the city.

Getting Around

No car is needed: Portland’s mass transit system takes you everywhere.

Where to Stay

Ace Hotel

A unique little place on the edge of the Pearl District, geared to the creative class.

The Benson

A landmark 1912 hotel with a fantastic old-world lobby.

Hotel deLuxe

A Provenance Hotels boutique property that channels Old Hollywood with vintage movieland photos on every floor.

Hotel Lucia

The sister property to the deLuxe, with David Hume Kennerly photographs.

Where to Eat

Higgins Restaurant & Bar

Jake’s Famous Crawfish Restaurant

Paley’s Place

Portland Farmers’ Market

Proper Eats Market & Café

Simpatica Dining Hall

A Portland favorite open only on weekends, with chef-owners Jason Owens and David Kreifels changing the locally sourced menus nightly.

Where to Go Out

Acme Food + Drink

Alibi Restaurant and Lounge

Portland’s only Tiki bar, with plenty of kitsch and charm.

Bettie Ford Lounge

Doug Fir

Jimmy Mak’s

Red & Black Café

Voodoo Doughnut & Wedding Chapel

Where to Shop

Alma Chocolate

140 NE 28th Ave.; 503/517-0262.

Columbia Sportswear Company

The flagship store, housed downtown in an 1888 basalt-columned building. 911 SW Broadway; 505/226-6800.


A smart boutique featuring Portland designers. 520 SW Ninth Ave.; 503/220-0920.

Powell’s City of Books

1005 W. Burnside St.; 503/228-4651.

Torso Vintages

First-rate vintage clothes with high-end prices. 36 SW Third Ave.; 503/294-1493.

What to Do

Concerts and Festivals

Portland is a great city for the arts year-round. Summer brings Summer Concerts at Oregon Zoo (oregonzoo.org), the Safeway Waterfront Blues Festival (waterfrontbluesfest.com), Chamber Music Northwest’s Summer Festival (cmnw.org), and the Portland Institute for Contemporary Art’s über-edgy TBA (Time-Based Art) Festival around the city (pica.org). Fall and winter’s offerings include the contemporary dance series White Bird (whitebird.org), and the Oregon Symphony (orsymphony.org) and Portland Opera (portlandopera.org) seasons. February’s big headliner is the renowned Portland Jazz Festival (dx.jazz.com).

Japanese Gardens

In a city of beautiful gardens, this is the prettiest.611 SW Kingston Ave., Washington Park; 503/223-1321; japanesegarden.com.

Live Wire

The monthly taping of this whimsical radio variety show at the Aladdin Theater is a Portland tradition. 3017 SE Milwaukie Ave.; livewireradio.org.

Portland Art Museum

1219 SW Park Ave.; 503/226-2811; portlandartmuseum.org.

Whether it's high-energy rock, angst-driven ballads, or smooth lounge,music from Portland is marked by its intelligence and authenticemotion. T+L corralled a panel of locals and wistful expatriates tocompile a playlist of ten key tracks from the past decade.

—Kathy Roberson

Dandy Warhols “Bohemian Like You” (2000)
Chain-smoking cool pokes fun at itself.

The Decemberists “Engine Driver” (2005)
Music to help you savor a rainy afternoon.

Pink Martini “Let’s Never Stop Falling in Love”
For your next tongue-in-chic cocktail party.

The Shins “The New Slang”
Beware: impossibly catchy, though you’ll never understand the words.

Stephen Malkmus “Baby C’mon” (2005)
Who knows what he’s talking about?It just rocks.

Quasi “Goblins and Trolls” (2001)
A novel twist on love.

Elliott Smith “Waltz #2 (XO)” (1998)
A new standard for ballroom-dance class.

Helio Sequence “Everyone Knows Everyone” (2004)
A strange collision of harmonica and electronica.

Menomena “Wet and Rusting” (2007)
Feels like driving out of town at sunrise.

The Thermals “A Pillar of Salt” (2006)
What if punks took over a Catholic-school graduation?

Hotel deLuxe

Old Hollywood-style glamour prevails at this elegant, slightly-off-the-beaten-path hotel; you’ll feel it from the moment you ascend the wide marble steps into the grand lobby, with its ornately carved moldings and coffered ceilings. At the dark, wood-paneled Driftwood Room (one of Portland’s iconic lounges), local deal-makers hobnob in cushy leather banquettes; sophisticated diners frequent the restaurant, Gracie’s, which serves globally influenced Pacific Northwest cuisine. The old-school plushness is reinforced in the 130 rooms, with their angular Art Deco-esque furnishings, crystal lampshades, and black-and-white stills from classic films adorning the walls (more modern nods to entertainment—flat-screen TV’s and iPod docks—are here, too). The extra $20 for a King Feature suite which includes an elongated sitting area as well as a bedroom is worth the splurge.

The Benson

This 14-story hotel with brick siding dates to 1913 in downtown Portland, featuring premium century-old elements like Italian marble, Austrian crystal chandeliers, and Russian walnut. Each room contains flowing drapes, a flat-screen TV, and complimentary bamboo robe; but only the Grand Suite has a baby grand piano, and only the Presidential Suite has hosted every President since William Howard Taft. The Benson has two on-site restaurants. The casual, banquette-lined Palm Court has a breakfast buffet, lunch, and dinner. El Gaucho, an on-site Argentinean steakhouse with shocking blue walls, is dinner only.

Ace Hotel

This hotel is pure Portland: creative, authentic, irreverent. Rooms in the revamped 1912 hotel are decorated with murals and fitted with vintage claw-foot tubs; bedside tables are fashioned from secondhand tomes (the famous Powell’s Books is just down the block). It’s no wonder bands on tour like to stay here: there are in-room turntables and vintage LP’s, and guitar strings for sale at the front desk. Staff dressed in Nom de Guerre–conceived ensembles (button-down shirts, crisp Dickies pants) are as cool as the surroundings.