Play in Portland’s Shadows

1. Where to Stay

Ace HotelPhoto: Courtesy of Lauren Coleman

Relive the flophouse scene from Drugstore Cowboy (parts of which were filmed here in 1988) at the Ace Hotel (from $95), a newcomer to downtown’s Pearl District. Rooms are tiny but stylish with scratchy Pendleton Woolen Mills knits, murals by local street artists (Brent Wick’s giant cat room is a favorite), and iPod docks and turntables.

See Portland’s version of a rock-and-roll hotel—a mantle held by the Chateau in L.A. and the Chelsea in New York—at Jupiter (rooms from $114), a sixties roadside motel gone fastidiously mod. After catching an indie-rock show at the attached Doug Fir Lounge, join the after-party spilling over into the driveway.

For more peace and quiet, try the less cool but just as comfy McMenanins Kennedy School (from $99) in working-class Northeast Portland. On the site of a former elementary school, the property now includes adult pleasures like a soaking pool, a brew-n-view (i.e., a movie theater that serves beer), and a brewery.

2. Where to Eat

Le PigeonPhoto: Courtesy of Jeremy Lanig/Ian Lynam Creative Direction

Sneak into Portland’s secret breakfast spot du jour, the vegetarian-friendly Beaterville Café (201 N. Killingsworth St.; 503 735-4652). Waitresses inked with tattoos hover over fifties chrome-trim tables, serving strong coffee and tasty, egg-based breakfasts, vegan alternatives, and biscuit sandwiches named after vintage cars.

Watch one of the country’s hottest young chefs in action at Le Pigeon, the food-magazine-anointed platform for 27-year-old Gabriel Rucker. The small, rustic space provides the setting for bold, daily-changing dishes like duck pancakes and apple sauce, swordfish with lobster mushrooms, and sweetbread with smoked veal tongue.

Put yourself in the capable hands of local darling Naomi Pomeroy, who hosts pre-set prix fix dinners ($45) and brunches ($30) at her new 24-seater, Beast. The Northeast Portland restaurant opened this September with a palette of charcoals and pinks, a black chalkboard scrawled with chef’s notes, and an open kitchen.

3. What to Do

Crystal BallroomPhoto: Courtesy of McMenamins

Portland’s best clubs pride themselves on remaining small, casual, and dark—almost too dark, since even locals have a hard time finding them. The murkiest of them all may be Towne Lounge, hidden in a converted Art Deco funeral home on the edge of Southwest Portland. It is the place to see burlesque drag acts, experimental and obscure bands like beat-heavy, electro-pop makers Reverse Dotty and the Candy Cane Shivs, and other boundary-blurring performance artists.

You probably didn’t cross the continent to sit in a dank, smoky strip club, but strangely enough, Portland boasts one of the warmest and female-friendliest flesh markets in the country. Mary’s Club, the city’s oldest, opened in 1954 and is peppered with just the right amounts of erotica and irony. Grab one of the Naugahyde booths and join the respectful co-ed audience as tattooed art chicks gyrate to the latest Belle & Sebastian EP.

You’d be hard-pressed to visit Portland without encountering a McMenamins watering hole. But unlike the other 54 uniformly decorated “microbrew” venues, the grandiose Crystal Ballroom is a fixture on the local music scene. It draws big-name indie acts like the New Pornographers and Peter, Bjorn and John, plus members of local collectives like the Decemberists and Pink Martini, who can often be spied checking out smaller acts at the annex space, Lola’s Room.

4. Insider’s Tip

Simpatica Dining HallPhoto: Courtesy of Amy Ouellette

Underground supper clubs have a cult following in these parts. Most are semi-secretive and nomadic, roaming from restaurants to farms to a chef’s backyard from week to week. But Portland being semi-socialist, they’re open to everyone (as long as you reserve ahead). Some favorites: Simpatica Dining Hall’s geographically themed weekend dinners ($45 without wine), and the East Side Dining Club’s monthly Sunday suppers held in new restaurants around town ($55; sample menu: “Pork, Pickles, and Preserves”).

5. An Oddball Day

Burnside Skate ParkPhoto: Courtesy of SkateOregon 2000-2006

Often overlooked in favor of other “emerging” neighborhoods like NW Alberta and Mississippi Streets, the not-yet-gentrified SE Industrial Zone hides thrift stores and discreetly marked restaurants and bars among its faceless office warehouses. Start under the Burnside Bridge at the illegally built (and later, city-sanctioned) Burnside Skate Park, where Gus Van Sant’s latest skate-punk psycho-thriller, Paranoid Park, was filmed. Less than a mile south, check out Small A Projects, a tiny contemporary gallery with surfacing artists like Zoe Crosher, whose Out the Window: LAX project features photographs taken from 31 different hotels around the Los Angeles airport. Next, head a quarter-mile north to score repossessed vintage furniture at City Liquidators. Finally emerge from the shadows by climbing up to Rocket’s rooftop for catfish pirogis, stuffed squash blossoms, and fabulous skyline views.

6. Related Links

For punchy, amateurish feature writing as well as music, arts, and restaurant listings, look to the Willamette Weekly.

Portland Food & Drink is the best source for online menus, news on restaurant openings, and snarky, user-penned feedback.

Keep Portland Weird is more than just a bumper sticker: It’s a Website dedicated to chronicling “your garage bands, your pub crawls, your pillow fights.”

Two of Portland’s most popular pursuits—biking and beer drinking—are obsessively blogged about at PDX Beer and Bike Portland.

Play in Portland’s Shadows