Angel Face (pictured above)
14 NE 28th Ave., 239-3804, angelfaceportland.com.
This twee bar serves lovely oysters and steak tartare along with improvised drinks, inside a luxury pillbox with hand-painted "wallpaper." Order a classic Negroni, or ask world-class bartender Kelley Swenson for an "earthy gin cocktail" or "something spicy with bourbon," and see what happens.
2733 NE Broadway, 662-8454, halepele.com.
Hale Pele takes tiki to its full potential with some of the best cocktails in town. The classic 151 Swizzle is like a combustible snow cone of overproof rum, while the signature Sailor's Grog perfectly combines multiple rums, falernum and ginger beer.
5424 NE 30th Ave., expatriatepdx.com.
Kyle Webster and Naomi Pomeroy's Expatriate is self-consciously bookish and exotic, with bartenders who double as vinyl spinners. But try the No. 8—a tonic of Pierre Ferrand 1840 cognac, Dickel rye, génépi, Italian vermouth and Regan's orange bitters—or the sweeter Dorleac with vodka, Aperol, lemon, honey, elderflower and Angostura bitters. You will feel privileged to live such a smart and fashionable life.
The Knock Back
2315 NE Alberta St., 284-4090, theknockback.com.
The Knock Back began as a bit of a muddled experience, with a fire pit, occasional music and a downright weird drinks menu. But now, with first-rate bartender Jesse Card, they've added the muddling for real. Card serves frozen Spanish coffees and whiskey cocktails mixed with quince, pumpkin or Madeira, forging the Knock Back's surprising transition to excellent cocktail bar.
4057 N Mississippi Ave., 284-6669, interurbanpdx.com.
Interurban is a bit like a mountain chalet owned by your terribly rich and discriminating friend, with discriminating drinks to match. The bar's standards combine classic mixtures with odd, idiosyncratic flourishes—the Fighting Cock bourbon and Cock 'n Bull ginger beer of the Sword Fight—while the menu is rounded out by refugees from Kappler's 1895 cocktail book, including a dry Dundorado featuring Ransom old tom gin, Calisaya and Italian vermouth.
720 SE Sandy Blvd., 265-8807, rumclubpdx.com.
The now-classic Rum Club welcomes first-daters, out-of-towners, patio smokers and especially cocktail aficionados who avoid the inflated prices and vest-and-bow-tie fussiness of westside mixology shrines. They specialize in many daiquiris and excel at fresh-fruit blended drinks, but don't overlook the mainstay Pedro Martinez, which mixes aged rum with maraschino, Torino vermouth and bitters.
Vintage Cocktail Lounge
7907 SE Stark St., 262-0696.
This Montavilla spot—staffed seemingly exclusively by bearded men—often makes cocktails with dulcet, subtle tones rarely tasted elsewhere among Portland lounges often bent on the fiery, herbal and medicinal. For example, a gently beige Ainsley made with rum, génépi and pineapple; a Nameless made with chamomile; or a Warm Hand, Cold Heart that thickens chocolate vodka and Kahlúa with stout.
The Richmond Bar
3203 SE Division St., 208-3075, therichmondbar.com.
The cocktails at this cozily tasteful bar skew to the sweetly medicinal, including a gin-absinthe Le Reveiller that easily lives up to its name, and an herbal Sassafras named after the dominant note in the Root spirit mixed with tequila, mezcal and Cynar—it's like sarsaparilla with some heat in the nose.
5008 SE Hawthorne Blvd, 232-6333, thesapphirehotel.com.
At the Sapphire Hotel—which touts its past as a den of iniquity but whose dim light now conceals mostly coy first-date blushes—creamy richness flushes cheeks in a snifter of the Sweet Surrender's rum and sharp coffee liquor. But their most popular drink by far remains the novelty Most Popular Drink, a mix of sweet and tart that's served with Pop Rocks.
2500 SE Clinton St., 808-9999, savoypdx.com.
Savory Tavern has an under-the-radar cocktail program with unusual focus: a list of Tom Waits-themed "Mule Variations," house-bottled cocktails, pickleback flights, apple brandy drinks and infusions that include an espresso fernet. It'd be a vision of comfort if not for the occasional black or cayenne pepper.
835 SW 2nd Ave., 222-0047, luclackitchen.com.
With its many bar snacks and skewers alongside the noodle bowls, Luc Lac is actually a much better cocktail bar than it is a Vietnamese restaurant. The Single Knight, mixing Four Roses bourbon with pho syrup, is an inspired invention by bartender and owner Adam Ho, as is the green-tea infusion in their Drambuie. But the most popular drink for happy-hour sippers is the Hello & Goodbye, essentially a rum soda made with carbonated coconut water.
614 SW 11th Ave., 384-2347, jackknifepdx.com.
Jackknife's Bonnie Parker cocktail is one of the best in town—a balanced, comfortingly sweet, copper-cupped blend of bourbon, pecan and maple honey that might actually make you gasp audibly on the first sip. But a nice piece of whimsy at the hotel nightclub—and excellent happy-hour haunt—is their "classic hotel cocktails" menu, including an Astor featuring Hennessy VS, maraschino, lemon, egg white and absinthe rinse.
1331 SW Broadway, 222-7673, ravenandrosepdx.com.
Located above the Raven & Rose restaurant in the historic Ladd Carriage House, the Rookery's massive fireplace, cavernous attic ceilings and sheer upholstery exude class. While the beer selection is nothing to sneeze at, this bar is more appropriate for a fantastic Sim's Old Fashioned using Eagle Rare 12-year bourbon. (The Sim in question is Simeon Reed, the namesake of Reed College.) Or order from the Old Mr. Boston De Luxe Official Bartender's Guide, one of 185 bartending guides on hand.
Multnomah Whiskey Library
1124 SW Alder St., 954-1381, mwlpdx.com.
Climb past the long line on the stairs leading to Multnomah Whiskey Library and you'll find a little secretary's desk. You can wait, or you can give your name and number, and maybe they will call. Maybe they won't. If you get inside, there's dimpled leather furniture, a fireplace flanked by stacks of split wood and two menus—one for spirits they're "concentrating on," the other listing bottles on the shelves—with drinks going for $8 or $54, depending on what you like.
Pepe Le Moko
407 SW 10th Ave., 546-8537, pepelemokopdx.com.
Big-shot bartender Jeffrey Morgenthaler's sotto voce bar revives much-maligned classics—dirty, guilty pleasures—in an NYC-style basement speakeasy. There's a $13 Long Island iced tea, an impeccably well-mixed Amaretto sour, and an espresso martini dressed up with a zingy dash of lemon oil. The Grasshopper is like an alcoholic Junior Mint, a boozy milkshake of creme de menthe, creme de cacao, ice cream, fernet and sea salt.
1610 NW 23rd Ave., 360-1281, stjackpdx.com.
St. Jack is the rare excellent cocktail spot to focus on gin cocktails. Get the flagship—a cardamom-spiced, gin-blossomed Barrel-Aged Bijou—or any of its gin cocktails, and you might end your night feeling dirty, drunk and superior all at the same time.
2282 NW Hoyt St., 221-0098, mcmenamins.com.
Consider it an experiment; despite establishing some of the best brandy and whiskey in Portland—and certainly the only outfit with both the resources and patience to age brandy nine to 13 years—McMenamins bars remain beer-focused affairs. Well, not anymore. Ram's Head is now a dedicated cocktail spot, focusing on the brothers' own spirits but also bringing in craft ingredients from other local distillers. Consider: A cocktail bar dedicated to terroir.
1015 NW Everett St., 445-8109, teardroplounge.com.
Teardrop Lounge offers a roster of meticulously crafted libations, served by mixologists who will turn your highball or martini glass into an art canvas on a teardrop-shaped bar. The Elk's Own cocktail is nearly identical to the award-winning Elk's Fizz crafted by Peter Sindar in 1901: a frothy blend of rye whiskey, port, egg white and lemon that goes down like an earthy meringue. The Borrowed Time is a house original blending tequila, bitters, blood orange, amaro, marshmallow root tincture and Chartreuse elixir; the smoky, sweet flavor recalls a cigar laced with orange zest.
801 NW 23rd Ave., 477-9505, pdxfireside.com.
Booze alchemist Chauncey Roach—formerly at Ración—has augmented co-owner Sue Erickson's estimable signature Backyard Grillin' mezcal-amaro cocktail with brilliant warm-day companion Heat Index, a pan-oceanic tropical fusion of multiple rums with arak and mint shiso. Erickson has added a crazily fig-forward Scarlet Fig mashed up with aquavit that first brutally shocks and then comforts, like a pickup artist who's read all the books.
Vault Martini Bar
226 NW 12th Ave., 224-4909, vault-martini.com.
As a cocktail bar, Vault is almost creaky at 10 years old in a Portland liquor scene that's entirely reinvented itself in the last six or seven. The basement lounge makes meticulous cocktails of the resolutely post-Prohibition style: far more bourbons than ryes and far more infused vodkas than either. Think bubbly mixers, coffee drinks and flavored vodkatinis of every stripe imaginable, plus rum mixed with guava.