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Can a place be too perfect?

In recent years, Portland, Oregon, has acquired a reputation as a big city with a small-town quality of life: The air is fresh, the food is organic, the streets are paved with good intentions
Washington Park
Washington ParkJohn Clark / Budget Travel
/ Source: Arthur Frommer's Budget Travel

When I first heard Loretta Lynn sing, “Well, Portland, Oregon, and sloe gin fizz / If that ain’t love, then tell me what is,” I wanted to write her a letter. “Dear Loretta,” it would say. “Have you ever considered Havana, Cuba, and a bottle of rum? How about Madrid, Spain, and a lusty Rioja?” As far as I could tell, there was nothing particularly seductive about a city where plug-ins for electric cars were installed nine years ago, where the most prominent new building was made with recycled material, where you’d be hard pressed to find a street without a clearly marked bike lane.

There’s an admirable, almost intimidating conscientiousness to the way people in Portland live, which has little to do with sensual abandon. Not only does a spotless, fast, and cheap ($1.70) light rail run from the airport to the middle of the city, but there was also a guardian angel posted near the ticket machine to facilitate the process. Forty minutes later, I was on the tree-lined, cobblestoned streets downtown. A policeman on a mountain bike directed me to the Hotel Lucia, where the staff offered me a tart green apple and plied me with maps and restaurant recommendations. Wandering around, I noticed kiosks stocked with brochures. They were manned by sidewalk ambassadors, armed with pocket PCs, posted specifically to answer tourists’ questions. It was like Disneyland with more overt politics.

But every time I thought I had Portland figured out, something came along and turned my theory upside-down. It can be as arch as it is earnest, as sophisticated as it is folksy, as obsessive as it is easygoing—and although it may lead with its utopian aspirations, it has plenty of dystopian secrets. Portland, I was surprised to learn, has more strip bars per capita than any other U.S. city.

Maybe Loretta was on to something.

It started, as these things do, with smart planning. Twenty-five years ago, the regional government created an urban growth boundary, confining new development to established neighborhoods in order to minimize sprawl. The result is a city unfettered by strip malls and prefab developments; instead, Portland is a patchwork of neighborhoods, each a sort of self-contained, distinctive ecosystem.

The Willamette (rhymes with “Damn it”) River snakes through the city, separating the east side from the west; Burnside Street divides north and south. Most of Portland’s traditional attractions are on the west side, including its downtown. At lunch hour, Pioneer Square—an amphitheater smack in the city’s center—is filled with professionals eating delicious tacos and Ethiopian food sold from hand-painted carts. But unlike so many American cities, downtown Portland continues to live and breathe at night and on weekends. Every other evening in Pioneer Square, weather permitting, there’s a symphony or a youth choir or an Italian cultural festival—or at the very least, a street musician banging noisily on plastic buckets.

Most of downtown Portland is shiny and new, but there are vestiges of the 19th century, when it was a brawny logging town. In the lobby of the Governor Hotel, leather couches and armchairs cluster around a huge marble fireplace. The hotel restaurant, Jake’s Grill, is a classic steakhouse: mosaic floors, stiff martinis, and Frank Sinatra on the sound system. Wilf’s, in the city’s fin de siècle train station, transports guests to an even earlier era, a time when train stations were associated with passionate farewell kisses. It’s a piano bar with flocked wallpaper, chandeliers, and huge velvet banquettes. The night I was there, a woman in cat glasses, accompanied by a pianist and a conga player, crooned torch songs and bossa nova for an eclectic crowd—commuters killing time, couples in their 60s, hipsters titillated by living an anachronism (many of whom she greeted by name).

A good number of cast-iron buildings in downtown’s Old Town still bear their old signs, mostly for theaters and western outfitters, but inside are some of the city’s most interesting shops. Portland may have more vintage clothing stores per capita than any other American city—and one of the best, if the most expensive, is Torso. Michellie, the imperious chatelaine who runs the place, talks as if each piece is a beloved child. “Those darlings won’t be with us for long,” she purrs, waving a bangled arm toward a row of Dior and Valentino gowns. Around the corner at The Monkey and the Rat, there are antique walking sticks, Indonesian marionettes, gleaming mango-wood vases, and intricately carved Thai spirit houses. In one more instance of Portland’s good intentions, the owner tells me that he prices his Asian imports as reasonably as he can, since he gets such good deals on them abroad.

On the elm-shaded streets southwest of Pioneer Square, known as the South Park Blocks, young couples, high on the joys of nesting, drift through the organic blackberries and fresh-roasted hazelnuts at the Portland Farmers Market. Families buy wholesome picnic lunches, then settle on the lawn, serenaded by a musician or four; and every week there’s a cooking demonstration by chefs from some of the city’s best restaurants. Portlanders take the politics of food very seriously. They want to know the provenance of their tomatoes and coffee and goat cheese. Consequently, food here tends to have a lot of modifiers. “Organic” is a given unless you’re at McDonald’s; “handcrafted” comes in a very close second; products are also “sustainably grown” or “fairly traded,” particularly if they’re from the developing world. This reigning ethos means that not only does the owner of local chain Hot Lips Pizza buy his organic vegetables from local farmers, but he can also explain in great detail about the method used to grow the wheat in his crust.

The uncompromising ethos about food production struck me as particularly Portland, as did the bearded volunteer at the entrance to the Classical Chinese Garden that afternoon. He suggested I remove my shoes upon entering—not for reasons of protocol, but because the stone paths, patterned like slashing raindrops, give a great foot massage. If I lived in Portland, I’d return again and again just to sit in the teahouse, an airy, two-story wooden pavilion with keyhole windows and latticed shutters, and a fountain trickling in the background. By now, I had come to expect esoterica from any menu, and I wasn’t disappointed. It informed me that the needles for silver needle tea had to be plucked within 48 hours of sprouting; and that the leaves for jade flower tea are roasted in a wok, then sewn into a flower that resembles a sea anemone. Jade flowers are so labor-intensive, tea farmers can make only 15 of them in one day. I ordered some strange and delicious snacks, too: roasted watermelon seeds sprinkled with cinnamon and anise; turnip cakes, the consistency of polenta and served with scallions and Chinese pesto; and a boiled egg that had been steeped in soy, star anise, and smoked black tea.

Asian culture makes frequent appearances around Portland, among them a long-running exhibition of early Chinese art at the Portland Art Museum, down the street from the Farmers Market. The museum also hosts diverse traveling exhibits, from 17th-century Dutch paintings to a show of photographs and lantern slides from a 1920s expedition to Tibet. Over the past five years or so, Portland has become a breeding ground for young artistic talent, and by October, the museum will have renovated a former Masonic temple to house modern and contemporary art. Some of the most playful—and controversial—work is being done by groups such as Charm Bracelet, notorious for dissing the art world by stuffing a huge vinyl elephant with discarded artists’ statements and gallery press releases. Before the 2004 presidential election, Red76 created 25,000 copies of voter information in the form of placemats, which were distributed at diners and truck stops nationwide. Ogle and Gallery 500 showcase emerging artists such as Chandra Bocci, whose recent installation (at Haze Gallery, since closed) featured plastic toy soldiers fighting with tiny pink-and-white pillows, and Matt Proctor and Eric Franklin, who constructed wooden tiki huts and igloos lit by neon tubes (after crawling through them, viewers submitted to an optical exam, and then were sent home with high-end eyeglasses).

The Pearl District is to Portland what SoHo was to New York 15 years ago, before it crossed decisively into mall territory. Formerly a neighborhood of sheet-metal warehouses and trucking distribution centers, it’s where the blue-chip galleries have staked their claim. There are also high-end boutiques selling French linens, children’s clothing fit for an English manor, canine tutus, and so on. The Pearl has a few relics of its former self. At Fuller’s Coffee Shop, regulars in feed caps sit around the horseshoe-shaped counter slurping acidic coffee. The menu is a throwback to the days when lo-cal meant a hamburger patty and a scoop of cottage cheese. Piazza Italia remains a sweet, family-owned place that serves outstanding pasta. Overall, however, restaurants in the Pearl have higher production values than elsewhere in Portland. They’re more lipsticked and perfumed, more likely to serve cocktails than beer. On weekends, Paragon feels a little like a dance club with no dance floor. The young, single crowd snacks on calamari with apricot jalapeño sauce. To appreciate the fantastic Northwest-fusion food, such as potato-wrapped wild salmon in chive coulis with marinated pear tomatoes and pea tendrils, you’re better off going on a quiet weeknight.

The quirks of Portland’s character are much more evident once you cross over to the east side. The first Thursday of every month, galleries in the Pearl stay open into the evening, and a few lay out platters of grapes and Camembert. On the street corners, accordionists play Edith Piaf songs. Meanwhile, galleries in Northeast Alberta, a neighborhood across the river, stay open late on the last Thursday of every month, and some encourage you to bring your own wine. A troubadour with iron-colored hair rasps Bob Dylan tunes on the stoop of a shuttered store, and folks from the neighborhood drag out card tables to sell homemade brownies and slices of blackberry pie. When I was there, an 8-year-old named Brian set up his own arcade game: For a penny a try, passersby could attempt to flick a plastic frog into a plastic bucket that was probably a few inches too high.

The art at Last Thursday didn’t really seem like the main point (although there were some lovely paintings at Talisman Gallery). More than half the fun came from dancing to live bluegrass in the parking lot, perusing the shamanic jewelry and artistically arranged junk being hawked by sidewalk vendors, and wandering into the shops on the main drag, also open late. Besides the funky boutique Tumbleweed, where owner Kara Larson sells flowery, home-on-the-range dresses she makes herself, there’s a real Mexican carnicería, Don Pancho’s, offering not just sides of beef, but also plastic roses and elaborate polyester wedding dresses. When the galleries and shops finally lock their doors, everyone fans out to a handful of restaurants and bars. Tin Shed is, indeed, a corrugated tin building with marigold walls and light fixtures constructed of side-by-side dinner forks. It’s quintessentially Portland—effortlessly charming and more sophisticated than it lets on, with wild mushroom ravioli and jalapeño mac and cheese.

Portland is blessed with a number of restaurants like this—unassuming, reasonably priced establishments that take food seriously without being uptight. Bread and Ink serves modern interpretations of comfort food in what was once a grocery store. It has the linoleum floors and green leather chairs of a 1950s coffee shop but the white tablecloths and brisk, professional service of a bistro. Another favorite, Pambiche, does gutsy Cuban food—pepper pot stew, garlic shrimp, and taro-root fritters—in a coral-colored building.

Even though Oregon makes some of the best wines around these days, beer is accorded equal reverence and described with the same nuance. The city has 34 microbreweries in the metropolitan area. The Lucky Labrador Brew Pub, in an old sheet-metal warehouse, brews a fantastic house ale. The back porch, where customers and their mostly big, mostly friendly dogs hang out at picnic tables, has the folksy feeling of a backyard BBQ.

The closest Portland gets to velvet-rope exclusivity is an event-cum-restaurant called Family Supper. It began as a dinner party at the home of Naomi and Michael Hebberoy, a couple that used to run a catering company called Ripe; it evolved into an invitation-only affair; and finally, Family Supper opened its doors to those lucky enough to get a reservation. Unmarked and unlisted, Family Supper is still more like a dinner party than a restaurant. The 40 guests are asked to arrive at 7:30 p.m. They spend the first half hour milling about the herb garden drinking wine or chatting with the chef in the open kitchen. At eight, everyone gathers in assigned seats at two butcher-block tables, and heaping platters of seasonally inspired Italian food are passed around. I had to fight my instinct to ask for a third helping of a rich sweet corn risotto with fresh truffles. For dessert we had blackberry cobbler topped with a cloud of barely sweet whipped cream.

Much less covert is the Pepto-Bismol-pink saltbox house where Lovely Hula Hands has staked its claim. The food veers from Southeast Asia to Cuba—Thai flatiron steak with sticky rice served in a take-out carton, Cuban pumpkin rice with tomato-coconut curry—while the décor is inspired by a grandma’s parlor, with leafy vintage wallpaper, Japanese prints, and an old mantle serving as a bar.

Down the hill and across from the railroad yard, drunken sailors and Polish immigrants used to gather for heated poker games in the White Eagle. Today, it’s a cozy parlor bar, with mosaic floors, an oak bar, and Oriental rugs, and it hosts country, blues, and rock shows. Upstairs are 11 small hotel rooms, perhaps the best deal in Portland at $30 to $50 a night, if you don’t plan on sleeping until after the music stops (between 11 p.m. and 2 a.m., depending on the night of the week). The White Eagle is run by a Portland-based company called McMenamins, whose business model is to buy historic buildings and transform them into bars and hotels while retaining as much of their character as possible. This being Portland, McMenamins is also known for brewing great beer.

McMenamins’ other Portland hotel, the Kennedy School, is in a quiet, residential neighborhood to the east. It’s an old grammar school transformed into a themed hotel. Former classrooms are furnished with formidable oak headboards, Oriental rugs, and tassled lampshades, and some choice details have been preserved, such as the chalkboards and the lockers. Movies are shown nightly in the former gymnasium ($3), and there’s an on-site pub with live music a couple of nights a week.

Further south, in the Hawthorne neighborhood, is another vivid reminder that Portland isn’t as young as it looks. Opened in 1927 to showcase silent films and vaudeville acts, Bagdad Theater still features the original Arabian Nights murals of snake charmers and sultans, from a time when the semiotics of ethnicity were a less volatile subject. The auditorium also retains its old red velvety seats, but some have been removed in order to make way for small wooden tables, which allow patrons to dine on pizza, microbrews, and local wine ($6.25 a glass, tops), while they watch second-run movies.

Hawthorne is Portland at its crunchiest. Incense seems to waft from every pastel-colored bungalow, and the old VWs in the driveways are plastered with free tibet stickers. In Other Words is a nonprofit bookstore that specializes in books by, for, and about women. Global Exchange is an import shop with an uncompromising fair-trade policy and beautiful wares: Tibetan prayer wheels, Mexican and Peruvian retablos, Indian bedspreads, and glazed Vietnamese tea sets. Powell’s for Cooks and Gardeners is an offshoot of Powell’s Books, the country’s largest independent bookseller (and a Portland institution). The main store, Powell’s City of Books, occupies a 74,000-square-foot building downtown, but the Hawthorne shop stocks the most obscure cookbooks you could ever dream up. Among the categories: ayurvedic, gluten-free, Amish, and Junior League. Then there’s Rimsky-Korsakoffee House, which falls somewhere between a ’60s coffeehouse and a Viennese café. Latter-day flower children in flowing skirts gather at night for coffee and cake in a Victorian house with a sloping front porch, and a swooning pianist plays Chopin and Beethoven on a scuffed baby grand.

Despite its earnestness—or perhaps because its residents need something to rebel against—Portland has its share of indie rockers, and most seem to be hanging out at Doug Fir. It’s an ironic derivative of a Denny’s-style coffee shop tricked out like a 1970s rec room as interpreted by an of-the-moment designer: faux-fur carpeting, curving vinyl banquettes, and late-night service. It’s also an homage to the archetypal mountain lodge, with antler chandeliers and cocktail tables rendered from tree stumps. On the ground floor is a music club that books rock, hip-hop, and big-name DJs. The restaurant caters to the late-night cravings of the clubgoers, who in turn help fill the rooms of the adjacent Jupiter Hotel, a revamped ’60s motor court offering rooms that have a playful Ikea aesthetic. On the patio, there’s a big fire pit where guests can gather round and drink a few beers.

Most of the time, though, Portland is a resoundingly nice place where people are genuinely concerned about the welfare of other people, whether those people live next door or in Nepal. In an impossibly sweet residential area called Sellwood, where every house is graced with a rosebush and children scampered home from the community pool in groups, holding hands, I came upon an intersection where, on one corner, there was a table with a large Thermos of tea and a half-dozen mismatched cups hanging from pegs. help yourself said a hand-lettered sign. On another corner, inside  a bamboo lean-to, there was a modest bookshelf and a chalkboard where someone had written, happy birthday, rebecca! A small plaque explained that this was Share-It Square, an effort to build relationships in the neighborhood.

You can see why I wanted to write Loretta that letter. All this noble goodness can be a bit of a drag. What usually makes a city interesting is friction—people rubbing up against each other, not always with mutual respect.

On my last day, I signed up for a walking tour of downtown. The guide pointed out the perpetually bubbling water fountains that were installed in the 1910s. “It’s rainwater,” he said, encouraging us to take a taste. He directed our attention to one about half a foot off the ground, and told us it had been installed for dogs. It was almost too much to bear.

And then something wonderful happened. As the tour guide rhapsodized about the monitors in the bus shelters that update commuters on the buses’ ETA every 30 seconds and the parking meters that know to refuse your money on the days when payment isn’t necessary, a cluster of punk-lite kids in dog collars and Converse high-tops started heckling him. They also suggested, in no uncertain terms, that all of us—the losers standing there listening to the lecture on public transportation—pack it in and go back home. The other tourists shifted their weight uncomfortably; they didn’t want anyone to puncture their utopian vision of Portland. But I found myself comforted. I needed a reminder that Portland is a real place with real people who get angry and everything.

It only made me love it more.

Where to spend more on a special dinner
On the back of the menu at Higgins is a manifesto explaining that the ingredients are local, seasonal, organic, and sustainable, and that in maintaining these standards, the restaurant preserves rural communities and decreases water and air pollution. Foodwise, this might translate into handcrafted pastrami, or pheasant and venison terrine with sour cherry mustard. In a lantern-lit room, Noble Rot serves unusual small plates—pork and squab terrine, eggplant and lamb cannelloni with a yogurt sauce—but wine is the real passion here. The vaguely unappetizing name refers to a grape fungus that produces a sweeter, richer flavor in wines. There are up to 50 wines by the glass and five flights (samplers of three wines in two-ounce pours).


  • Governor Hotel 614 SW 11th Ave., 800/554-3456,, from $129
  • Hotel Lucia 400 SW Broadway, 877/225-1717,, from $139
  • Jupiter Hotel 800 E. Burnside St., 877/800-0004,, from $79 ($50 Get a Room rate after midnight)
  • Kennedy School 5736 NE 33rd Ave., 888/249-3983,, $84–$94
  • White Eagle 836 N. Russell St., 503/282-6810,, $30–$50


  • Bread and Ink Café 3610 SE Hawthorne Blvd., 503/239-4756, jerk chicken sandwich $8.75
  • Family Supper 2240 N. Interstate, 503/493-9500, three-course dinner $25
  • Fuller’s Coffee Shop 136 NW Ninth Ave., 503/222-5608, pancakes and eggs $3.50
  • Higgins 1239 SW Broadway, 503/222-9070, pastrami sandwich $10
  • Hot Lips Pizza 1909 SW Sixth Ave., 503/595-2342, large cheese pizza $13.25
  • Jake’s Grill 611 SW 10th Ave., 503/220-1850, cheeseburger $8
  • Lovely Hula Hands 938 N. Cook St., 503/445-9910, Thai flatiron steak $12
  • Noble Rot 2724 SE Ankeny St., 503/233-1999, Pacific cod with bacon and sautéed greens $13
  • Pambiche 2811 NE Glisan St., 503/233-0511, Creole chicken $12.50
  • Paragon 1309 NW Hoyt St., 503/833-5060, wild-mushroom-stuffed chicken $17
  • Piazza Italia 1129 NW Johnson St., 503/478-0619, linguine squarciarella $13
  • Tin Shed 1438 NE Alberta St., 503/288-6966, jalapeño macaroni and cheese $6


  • Don Pancho’s Market and Carnicería 2000 NE Alberta St., 503/282-1892
  • Global Exchange 3508 SE Hawthorne Blvd., 503/234-4049
  • In Other Words 3734 SE Hawthorne Blvd., 503/232-6003
  • The Monkey and the Rat 131 NW Second Ave., 503/224-3849
  • Powell’s Books for Cooks and Gardeners 3747 SE Hawthorne Blvd., 503/235-3802
  • Powell’s City of Books 1005 W. Burnside St., 503/228-4651
  • Torso 36 SW Third Ave., 503/294-1493
  • Tumbleweed 1804 NE Alberta St., 503/335-3100


  • Bagdad Theater 3702 SE Hawthorne Blvd., 503/236-9234
  • Doug Fir 830 E. Burnside St., 503/231-9663
  • Lucky Labrador Brew Pub 915 SE Hawthorne Blvd., 503/236-3555
  • Rimsky-Korsakoffee House 707 SE 12th Ave., 503/232-2640
  • White Eagle Saloon 836 N. Russell St., 503/282-6810
  • Wilf’s Union Station, NW Sixth Ave. and Irving St., 503/223-0070


  • Classical Chinese Garden NW Third Ave. at Everett St., 503/228-8131,, $7
  • Gallery 500 420 SW Washington St., Ste. 500, 503/223-3951,
  • Ogle 310 NW Broadway, 503/227-4333,
  • Portland Art Museum 1219 SW Park Ave., 503/226-2811,, $10
  • Portland Farmers Market South Park Blocks at Portland State University between SW Montgomery St. and SW Harrison St., 8:30 a.m.–2 p.m.
  • Talisman Gallery 1476 NE Alberta St., 503/284-8800,