By Jeeves! Checking out at Multnomah Whiskey Library
By Jeeves! Checking out at Multnomah Whiskey Library

Multnomah Whiskey Library: THE DISCRIMINATING TIPPLER

Come for: The Scofflaw, a classic take on a Prohibition-era cocktail (rye whiskey, dry vermouth, fresh lemon, and grenadine) 
Come back for: A surprisingly deep selection of tequilas, which nearly rivals MWL’s whiskey selection in breadth

If Portland’s quirk mated with a 1920s speakeasy and a conspiracy theorist’s “smoke-filled room”—that fabled place where brandy-drinkers launched dark horses for president —the progeny might look a lot like the Multnomah Whiskey Library. At the top of a flight of stairs, just beyond an unmarked door, a host asks for your name—yes, your full name—and your phone number. (They’ll call you when your table’s ready.) Somehow, such rituals feel refreshingly stuffy. Yes, there are hours-long waits, portraits of frowning white men lining the walls, and library “memberships” available for $500 a pop. But there is also cool, dark comfort, an academic devotion to liquor, and an unhurried, intimate atmosphere, complete with a massive fireplace and lawn jockeys. “Head Librarian” Tommy Klus’s drinks are superb and mixed tableside: the house rye manhattan (easy to make, hard to make great) is a standout. Skip the food and delve into the Library’s 1,500-strong bottle roster. You might just find there’s a power broker hidden in your Portland soul after all. 1124 SW Alder St

Sea-worthy: Scan eats and drinks at Radar.
Sea-worthy: Scan eats and drinks at Radar.

Radar: FOUND AT SEA

Come for: Chocolaty-good Night Owl, brimming with Elijah Craig bourbon, cocoa-nib Ramazzotti, and toasted pecan bitters
Come back for: Some face time with co-owner Lily Tollefsen, whose charm has earned her our vote for the Mayor of Mississippi (she’s now the president of the Mississippi Avenue Business Association)

Radar’s glowing, raw-brick space, dominated by an open kitchen tucked behind a swooping bar counter, easily reels in neighbors, strolling couples, and restaurant industry vets off the street. The maritime-tinged spot, run by husband-and-wife team Jonathan Berube and Lily Tollefsen, keeps its catch by serving as a relaxed-but-classy hideaway on a street that’s become increasingly rambunctious. Berube runs the kitchen, mingling strong Scandinavian influences with Northwest twists and Northeast seafood (they fly in smoked bluefish weekly for pâté) while Tollefsen mans the bar, which boasts top-notch drinks she dreamed up with a childhood friend, national cocktail superstar Alex Day (Death and Company in New York and LA’s Honeycut). The European Union—a heady blend of Hayman’s Old Tom gin, Busnel calvados, sweet vermouth, Strega, and bitters—is as complex as its namesake’s politics, and that Night Owl is one of our fave bourbon drinks in town. Insider tip: Broder Nord is running a 45-minute wait for brunch? Head up the hill to Radar’s warm, line-free environs. 3951 N Mississippi Ave

The Spare Room: THE DIVE AT THE END OF THE UNIVERSE

Come for: Cheap drinks, friendly service, and Portlandia-caliber oddness
Come back for: Monday karaoke/bingo night, where host Danny Chavez may accompany your warbles on the saxophone

On any given night, the clientele at this cavernous former bowling alley feels like a jagged cross-section of American culture: stubbly men grumbling over fumbles on Monday Night Football rub shoulders with young, hip people (not hipsters—those don’t exist here) belting out karaoke songs in the middle of the wide dance floor. Off-the-clock coworkers mingle with people killing time between loads at the laundromat next door. Indie folk rockers twang through live sets some nights; soul bands spark dance parties on others. Old and young bond over plates of overcooked noodles and tepid sauce on spaghetti nights. The bartenders flirt with everyone. (Don’t ask them what micros they have on tap; they don’t have any, and you’ll feel silly.) The Spare Room’s sectional “design” really feels like multiple bars: part pool-hall, part karaoke temple, part-hole-in-the-wall—making it the end of the line for both melancholic loners and big, boisterous groups in search of a fun spot to colonize for an evening. In a city not lacking in dive bars, the Spare Room stands head and slumped shoulders above them all: a supremely time-warped fishbowl refracting the weirdness still lurking at Portland’s core. 4830 NE 42nd Ave

THE NEW SOUTHEAST STUMBLE
Oso Market & BarTrifecta, Voicebox 2Dig a Pony 

Come for: Excellent wines by the glass, classic cocktails, and a side of wood-fired eats 
Come back for: Group karaoke madness and hipsters-meet-burbs dance parties

A few years back, the only thing keeping locals at the east end of the Morrison Bridge was traffic jams; now the area has exploded with chockablock eclectic tippling options. Start with an early-evening glass of peppery Côtes du Rhône and chorizo and blue cheese–stuffed dates at spare-yet-friendly wine bar and bottle shop Oso. Next, head a block east to Ken Forkish’s stylish wood-fired bakery/bar, Trifecta Tavern, to sip a port-syrup and applejack–spiked Jersey Devil carefully concocted by one of the wide bar’s fastidious mixers. At private karaoke wonderland Voicebox’s new east-side location next door, you can slurp sake cocktails in its spacious bar and spy on work groups and birthday revelers while you wait your turn ($4–7 per hour per person). A few aspirational rounds of Journey later, the gravitational pull of Portland’s unofficial rumpus room, Dig a Pony, will suck you in. Knock back a couple of Dirty Shirleys and join the massive bar’s shifting flotsam of revelers as they break into another Jackson Five–induced DJ dance party. Too New Portland for you? The dream of the ’90s is still alive two blocks away at affable dive Morrison Hotel, where the G&Ts are strong, the curry cauliflower bites are fried, and Alice in Chains is on the jukebox in perpetuity. SE Morrison Street & SE Grand Avenue 

Tilt: THE BLUE-COLLAR PEARL

Come for: Vikings on the Willamette, a frosty onslaught of crisp aquavit, Lillet, and sweet fig compote, fragrant with slapped sage
Come back for: Criminally good “Tilted” fries, smothered in chunky, scratch-made pork sausage gravy and, Dear lord, sprinkled with bacon

Swan Island’s beloved burgers and (Oregon) beers spot, which constructed its second location in the Pearl’s old General Electric distribution plant last December, is as American as apple pie. Or, rather, a sweetly tart “Pie Break” cocktail, which tops applejack, lemon, and a dollop of Portland’s own Don’s Spices #2 syrup with frothy egg whites. Upgraded Americana is a calling card at the new Tilt, which charms all comers with juicy, salty burgers oozing with American cheese and gut-busting toppings as well as flaky house biscuits. The space is devoutly industrial; a concrete and metal bunker where a giant, monochromatic American flag serves as décor and shop rags double as napkins. Order at the counter (behind the hulking drill press) and head to the gregarious bar side of the operation, where no-nonsense classics and house concoctions from bar whiz Nick Keane as well as nearly 100 whiskeys keep you lubricated until the genuinely great pub grub arrives. The echoing space, filled with generations-spanning clusters of coworkers, sports watchers, and mellow friends, is so roomy you may not spot the Ping-Pong table or the fireplace in back until your second drink. And you will get a second drink. And then maybe a slice of pie. They bake that in house, too, of course. 1355 NW Everett St