Kask

1215 SE Alder st; grunerpdx.com/kask.htm

FOR: The Art School Crowd
YOU’RE HAVING: High Desert Swizzle (Del Maguey Vida mezcal, raspberry shrub, lime, Demerara sugar)

Given the subtle genius of Kask’s design, it’s unsurprising that owner Chris Israel spent six years as an art director at Vanity Fair. Every detail carries the mark of intention, from the collections of stained-glass bottles to the vintage cut-glass tumblers magnifying a prism of barrel-aged cachaça. Kask oozes a modernist, Old West clubhouse aura, festooned with metal knickknacks and twisted culinary doodads. Friendly, focused bartenders theatrically twirl bar spoons and torch citrus for cocktails straight from Portland’s new mixology school, heavy on ryes and masculine spirits. Discerning imbibers, crouched on low-set schoolhouse stools, nibble the only food in the house: charcuterie and cheese, listed on chalkboard slabs. The curvaceous bar, like the tabletops, is crafted from a fallen walnut tree and supported by a wall of caged stones, perpetuating the house adage: “Everything here is on the rocks.” —Benjamin Tepler

Rum Club

720 SE Sandy Blvd; rumclubpdx.com

FOR: Old-School Rum Lovers
YOU’RE HAVING: Rum Club Daiquiri (rum, lime, maraschino, Demerara syrup, Angostura bitters, absinthe)

With a low-slung wood-paneled ceiling, darkly tropical wallpaper, vintage glassware, and a menu of long-forgotten classic cocktails, the Rum Club is a wonderfully weird little mash-up of tiki bar, South Pacific dive, and craft cocktail haven. It’s a place where Ernest Hemingway and Hunter S. Thompson might share a drink, and where you could easily saddle up at the bar and watch the sun’s golden glow slide across the walls over the course of a long, rum-drenched evening. Born of a long friendship between owners Mike Shea and Kevin Ludwig, the Rum Club shares a building with Beaker & Flask (which Ludwig also owns), and it showcases the same disciplined approach to cocktail chemistry. Indeed, the house daiquiri would convert the most adamant of disbelievers, with even-handed dashes of maraschino, Demerara syrup, bitters, and absinthe added to the original formula (rum, lime, sugar). For surprisingly tasty sustenance, direct your attention to the oddly eclectic menu of party bites, from pickled eggs to empanadas, pastas, and sandwiches. Just like everything else at the Rum Club, it’s a little weird … but it works. —RR

Luc Lac Vietnamese Kitchen

835 SW Second Ave; luclackitchen.com
FOR: Late-Night Spice Seekers
YOU’RE HAVING: Smoke & Mirrors (Carbonated slow-drip Vietnamese coffee, mezcal, Fernet-Branca, smoked sea salt)

Last year, Portland’s Ho brothers made the jump from a cramped, pho-centric food court to a soaring, late-night Vietnamese diner tucked away on a sleepy downtown corner. From behind a U-shaped bar, the black-vested brothers shake up frothy cocktails and run steaming bowls of beef broth to their customers tucked away in tall red banquettes under hand-muraled walls. While intimidating upon first read, their liquid concoctions are a wacky and wonderful list of creamy Vietnamese flavors and classic liquors. Mung beans tumble into jackfruit, skewered watermelon balls soak in hoppy Kölsch, and fish sauce finds its way into a Jameson cocktail. Best of all, the sweet-and-boozy mélange keeps going until 4 a.m. on weekends, and pairs perfectly with springy rice noodles in anise-flavored broth or piles of deep-fried fish sauce wings. Here’s to new late-night traditions. —BT

The Sweet Hereafter

3326 SE Belmont St

FOR: Thirsty East-Siders and Their Vegan Friends
YOU’RE HAVING: The Hereafter (vodka, bourbon, lemon, iced tea)

Northeast Alberta Street’s Bye and Bye has a new, good-looking brother down south: the Sweet Hereafter. Owned by the same six-person co-op, this expansive bar’s dark walls hold familiar paintings of iconic Americana, with antique typewriters and vintage football helmets stuffed between the rows of dark liquor and illuminated by caged orbs. Push through and you’ll find a huge outdoor seating area, perfect for wolfing down tangy lemongrass tofu bahn mi and buffalo subs with miso-chive cheese from an all-vegan menu that even carnivores will learn to love. The drink list is inspired by the classics, with a great Sazerac and a few killer tropical cocktails, but the true find is the namesake beverage: a Long Island–esque potion served in a quart-size mason jar, with enough vodka and bourbon to tranquilize a charging rhinoceros. —BT

Barwares

4605 NE Fremont St; smallwarespdx.com/barwares

FOR: Simple Pleasures … With a Twist
YOU’RE HAVING: The Whiskey (rye whiskey, garam masala simple syrup)

Clear is the new clever. And in a bar scene fast approaching a tipping point wherein witty drink names and endless cocktail menus become tiresome, Barwares offers the proof. Chef/owner Johanna Ware (the brains behind attached restaurant Smallwares) and bar manager Conrad Vollmer’s refreshingly candid menu includes the Gin, the Rum, the Agave, the Vodka, the Sake, the Scotch, and the Whiskey. None of them misfires, and each holds an enticing Asian nuance, from Hakutsuru plum wine to cardamom-infused rum, Thai chile tincture, and garam masala simple syrup. Whether you opt for one of these or plunge into the selection of sake, beer, and wine—helpfully arranged in categories of “Funky,” “Fizzy,” “Fruity,” “Earthy,” and “Rich”—your beverage will be best enjoyed with Ware’s sublimely “inauthentic Asian” plates, eaten on the vintage couch in the glow of a classic Monty Python flick on the projector screen. —RR 

The Old Gold

2105 N Killingsworth st; theoldgoldpdx.com

FOR: Friends of North Portland
YOU’RE HAVING: El Diablo (tequila, crème de cassis, Brew Dr. Lemon Ginger Cayenne Kombucha, lime juice, cayenne)

This much is certain: North Portland is thrilled about the Old Gold. The moment you step onto its freshly cemented patio and cross that oh-so-familiar threshold of the rolled-up garage door, you can feel a distinct sense of euphoria saturating the room. Because the Old Gold is just the bar this patch of Overlook needed—a cozy local watering hole where you just might run into a neighbor or strike up a conversation with a perfect stranger. But beyond its freewheeling, wide-open atmosphere, the bustling bar also boasts some uniquely admirable assets, among them a hand-hewn, wooden, White Stag–esque “Drink in Oregon” sign, a memorable elk burger and tofu banh mi, and, best of all, a spacious booth outfitted with a “Champagne Button.” (Push it, and your server will appear with Champagne. Really.) The cocktail menu makes a good-natured stab at mixing in kombucha, which doesn’t always shine. But six local taps and a chalkboard scrawled with an impressive, always changing selection of whiskeys offers surefire redemption. —RR

Riffle NW

333 NW 13th Ave; rifflenw.com

FOR: Serious Cocktail Geeks
YOU’RE HAVING: Riffle Collins (gin, lemon, lime, celery, absinthe, salt)

An evening spent at the bar at Riffle NW is akin to a grad-school class in drinking. Behind a perfectly bespoke bar, beverage director David Shenaut and his dapper cohorts have created a cocktail science lab, doling out professorial wisdom on bitters, aeration, and dilution; hand-carving ice cubes with Japanese woodworking saws; and carefully calibrating cocktails to dispense, perfectly carbonated, from a shiny row of taps. You might think it’s all a little overwrought—until you take your first sip. Every drink holds a sly wink of surprise, whether it’s the addictive celery essence of the Riffle Collins or the savory allspice dancing on a foundation of sweet cachaça in a drink dubbed the Leya. And because the cocktails are carefully arranged in food-friendly sequence, from aperitifs to light spirits to brown liquors, a beer cocktail, and finally, digestifs, pairing each with a bite from Riffle’s bar menu of creative, super-fresh seafood is a no-brainer. —RR

The Woodsman Tavern

4537 SE Division St; woodsmantavern.com

FOR: Bourbon-Loving Perfectionists
YOU’RE HAVING: Hunting Vest (Campari steeped in charred cedar, rye, vermouth)

Standing behind the bronze bar at the Woodsman Tavern is Evan Zimmerman, one of Portland’s best bartenders—and this particular restaurant’s high-proof beating heart. In his natty suspenders, Zimmerman is unflinchingly affable, encyclopedic in his knowledge of cocktails, and judicious with his pours. His motto—“elegant and understated”—runs deep through the Woodsman’s rotating cocktail list, from a tart, foaming “Blackthorn Sour” (sloe gin, apricot brandy, lemon juice, pineapple gomme syrup) to the “Judge, Jury and Executioner” (Old Weller bourbon, Amaro, cucumber, macerated Sichuan flowers), with its cool cucumber nose and spicy final kick. In an evening at this sturdy bar, questions are encouraged and feedback is welcomed. If you’re not in a cocktail mood, try a pint from one of the 16 curated taps, and don’t leave without a “pickleback”—Irish whiskey chased by a briny shot of pickle juice. —BT

Dig a Pony

736 SE Grand Ave; digaponypdx.tumblr.com

FOR: Portland Scenesters
YOU’RE HAVING: Sam Isaacs (bourbon, mint, blackberries, lime)

Dance-party madness spills onto SE Morrison Street from this one-year-old, DJ-fueled destination where great-looking people come to play and everyone else comes to watch. A tremendous horseshoe bar anchors the room, while sprawling white tile, Oriental rugs, and a 110-year-old piano set the stage for impromptu weekend raves. Svelte, speedy bartenders shake up a storm for an impressive 280-degree performance, and local DJs pump ’90s vinyl into the well-heeled crowd. Dig a Pony turns out a surprisingly crafty food menu, with a top-quality Painted Hills burger smeared with sweet onion jam, and a bowl of sautéed mushrooms and soft-poached egg mopped up with shoestring fries. The overall vibe? A time-tangling mix of modern sophistication and boomtown honkytonk. In a word: confidence. —BT

The Box Social

3971 N Williams Ave; bxsocial.com

FOR: Lovers
YOU’RE HAVING: The Thoroughbred (Torani Amer, brandy, maraschino, lemon, pomegranate shrub)

Portland may have found its quintessential date spot in the Box Social. Unsurprisingly, it comes courtesy of Shannon McQuilkin, co-owner of the city’s other quintessential date spot, the Sapphire Hotel. The Box Social aims for a level of sophistication matched to the modern Portland crowd, with floor-to-ceiling embroidered drapes; a long, tufted-leather banquette; a dark, candlelit mahogany bar; and a huge hand-painted mural of Portland’s twinkling cityscape. Sure, it might feel a bit Sex and the City for Portland’s hipster set, but this 1,000-square-foot box creates a little world that you can’t help but get lost in. An extensive menu of original, classic, and bubbly cocktails holds some deliciously potent creations—along with plenty of drinking vinegars, beer, and wine—while well-priced nibbles range from parmesan popcorn to a pitch-perfect butter lettuce salad and decadent fig compote panini. If this place doesn’t set the mood, we don’t know what will. —RR