What a Night of Drinking in Portland Looks Like

An unflappable mix of eccentric and enlightened, Portland, Oregon is currently amidst a mini-boom of drinking establishments. Dylan + Jeni capture its wonderful weirdness from afternoon cocktails to late night noodle bowls. This is Saturday Night in Portland. (Slideshow below.)

Kicking off the late afternoon with a Love in the Afternoon—rye whiskey pluot and lemon-basil-demerara soda—at Teardrop Lounge, one of Portland's most beloved and established craft cocktail bars.

Sean Hoard (left), the former bar manager at Teardrop Lounge and the co-founder of The Commissary, brandishing a Tequila Julep. And bar manager Tyler Stevens (right) whipping up a Best of Both Worlds, Pt. 2 [recipe below].

A close-up of The Best of Both Worlds—a big bowl of rum, Carpano Antica, The Commissary's raspberry gomme, lime, mint, Angostura and High Life. "Plus crazy straws and sometimes fire," says Hoard. [Recipe]

Saturday night stomach prep: A stop at North Portland's Barlow Tavern for a few beers and an order of chicken and waffles. According to Hoard, "Barlow Tavern is one of the few bars in town you can hit late one night and get brunch at the next morning."

The famed chicken and waffles, with two sides of broccoli for good measure.

Hoard and Donald Kennedy (right), the General Manager of the Ace Hotel, share a few beers at Saraveza. Not only is it one of the country's best beer bars, it also doubles as "the perfect neighborhood bar where you can "can watch football, eat Chex Mix and drink delicious beer."

Saraveza is also a "beer boutique," wherein you can choose from a huge selection of bottles for takeaway.

Once the sun goes down, things take a turn for the serious at Multnomah Whiskey Library, a giant booze emporium with more than 1,500 bottles. On the right, a bartender prepares a drink on one of the library's cocktail carts.

The impressive backbar at Multnomah and a full house of drinkers. The library offers memberships, which allow members to skip the (generally very long) wait to get in.

Doing how the Irish do.

The whiskey is working.

Crucial recharge at Sizzle Pie, one of Portland's best late-night spots. (It's open until 4 a.m. on Saturdays.)

Hoard hits the juke box at Sizzle Pie.

Everyone is clearly having a terrible time here.

Back to the booze at Pepe Le Moko, a new underground bar around the corner from the Ace Hotel—the handiwork of Clyde Common and its longtime bartender, Jeffrey Morgenthaler.

Morgenthaler's Blended Grasshopper [recipe] and bartenders Heather Sang and Daniel Parker Guidry at work.

Guidry mixing up a few strong drinks. "I don't know what he's making," says Hoard. "Something gross, I'm sure."

The last stop on the Saturday night train: Luc Lac. This is where you get a big, steaming bowl of pho to mitigate tomorrow morning's headache.

A perpetual layer of grime sits atop Portland’s increasingly shiny surface, which isn’t surprising considering the Pacific Northwest is the home of grunge, a movement whose aftershocks are still palpable in the city’s many dives and leftover saloons.

Equal parts underbelly, gentrifying hippie commune and “Silicon Forest,” the city has seen a boomlet of drinking establishments that embrace the idiosyncratic while attempting to reconcile the influx of money, East Coast expats and a general obsession for quote-unquote gastropub fare. Some of these places are watering holes under cover—restaurants, strip clubs and late night pho joints. Others are out in the open—breweries, whiskey bars and cocktail dens. The one thing they all have in common is happy hour.

Portland is a town that prefers to start early. At all hours of day, the city is all about hitting the bottle alongside plates of fried chicken at Tasty n Alder, bowls of Vietnamese vermicelli at Luc Lac and pans of wood-fired pizza at Sizzle Pie. At midnight, downtown crowds queue up between bar hops for a menagerie of food carts that line parking lot perimeters. A bite between drinking venues is requisite on any Portland itinerary—local or tourist—and subsequent drinks are never a far stumble.

Divided into quadrants, Portland’s neighborhood directions (Northeast, Northwest, Southeast, Southwest) have become the calling card for specific aspects of the city’s culture—and by extension, their drinking scenes. In the posh Northwest there’s Teardrop Lounge, one of the city’s cocktail scene keystones where Miller High Life-infused punches are served with equal meditation as Amaro Cobblers and Martinezes.

In the park-lined, civic-building dotted Southwest, Multnomah Whiskey Library ushers guests with reservations into its plush, leather-coated interior where a service cart tinkers quietly down the aisles with tasting flights instead of book stacks. Close by, the subterranean cocktail bar, Pepe Le Moko, anchors one corner of the Ace Hotel’s complex, lit each evening with a neon pink “cocktails” sign. Beneath, drinkers will find a menu that—at first glance—might seem nostalgic with its ice cream-suffused Grasshoppers and $13 Long Island Iced Teas, but the bar is far more serious, and the service more deft, than this whimsy might suggest.

In stark contrast to the glossier side of the river, the Northeast is a bucolic grid of homes, yards, elementary schools and affordable real estate, with neighborhood bars embedded within the quiet blocks. Barlow Tavern—the rare modern-day tavern—known for its fried chicken and waffles, welcomes neighbors with $1.50 tallboy beers on Tuesdays and $4 craft beers on Wednesdays (it’s always happy hour somewhere in Portland), while Saraveza, a beer emporium with a sweet vintage lacquer, doubles as a bottle shop. (Both Barlow and Saraveza are technically in “the North.”) For those in search of champagne, there’s the old Portland wine hangout Pix (now Pix / Bar Vivant), where a long list of sherry and Champagne at low markups prove that, really, everything is cheaper in Portland.

Further south, a pervasive hipster-cum-yuppie vibe has settled in with new condos popping up between old strongholds like Pok Pok and Clinton Street Pub. Ava Gene’s and the Woodsman Tavern have carried the neighborhood’s colonization with great wine programs, clean cocktail menus and sophisticated, but simple food. But even with the recent density increase, the quadrant’s dive bars abide. At Devil’s Point, Sunday nights are for Stripparoke (exactly what it sounds like), and at Reel M Inn, a bartender takes beer orders while simultaneously frying chicken behind the dive’s dust-coated bar, while, not far away, a stream of regulars wander down to Dot’s Café, a velvet painting-adorned vegetarian restaurant-dive that is open until 2:30 a.m.

Portland, it seems, has earned Shangri-La status with its unflappable mix of eccentric and enlightened, so infectious that even blasé, seen-it-all Brooklyners speak enthusiastically about the city as the West Coast’s “it” destination. Between Stripparoke, midnight noodle bowls, cheap craft beer and well-crafted cocktails, Portland is undoubtedly, one of America’s best places to escape for a cold one.