North/NE Portland
The Box Social
3971 North Williams
Owners Eric and Shannon McQuilkin have created a drinking oasis that has a speakeasy vibe but without the pretension. You won’t find arrogant bartenders sporting handlebar mustaches and vests here. The vibe is cozy and welcoming, with floor-to-ceiling windows looking onto the street and a large mural of the Portland skyline adorning the back wall. Drinks are carefully crafted, using artisanal ingredients. The extensive menu includes classic cocktails such as Manhattans and Boulevardiers as well as proprietary drinks such as the hot pepper tequila- and sage-infused Dirty Little Thief and The Story Teller, a nuanced libation featuring spiced sangria, pomegranate and brandy.
SE Portland
Vintage Cocktail Lounge
7907 SE Stark
As the name suggests, Vintage Cocktail Lounge is just that. A dimly lit establishment that prides itself on creating old-school cocktails. Owner Justin Atkins takes traditional recipes and recreates them with a modern-day twist. Opt for the Sazerac or a Hemingway-inspired Death in the Afternoon (absinthe and brut) or any of the many bourbons on display. Many of the spirits lining the bar wall are rare or hard-to-find and Atkins and his staff happily inform patrons of the source and history of said liquors. The space is small, with an intimate bar in the back and wooden tables in front.
Downtown/SW Portland
Departure
525 SW Morrison
Downtown Portland has a wealth of drinking establishments, many of them offering pricey but watered down cocktails. Located at the top of The Nines hotel, Departure is a departure (pun intended) from that mold. Yes, the drinks are pricey here but they aren’t weak. The bartenders know their spirits and alter drinks to your taste. Popular libations include the biting Siracha-infused Three-headed Elephant and the Tuk-Tuk, a concoction of rum, ginger beer and basil. The nautical-themed lounge can get rowdy on weekend nights. Opt for a weekday when you can easily score a choice spot at one of the outdoor tables, overlooking downtown and Mt. Hood in the distance.
NW Portland
Teardrop Cocktail Lounge
1015 NW Everett
Ah, NW Portland. Where the frat boys go to play. Thankfully, not every bar along this stretch of town caters to a boisterous crowd. Teardrop Cocktail Lounge is one of the hottest bars to open in the Pearl district in recent years. Owner Daniel Shoemaker pays homage to classic cocktails, giving credit to the inventor, and puts his own stamp on cocktail history with deliciously inventive house drinks, using homemade tonic water and tinctures. Eighties rockers Katrina and the Waves would do well with the cacacha and St. Germain-infused Walking on Sunshine and political rabble rowsers would agree that there’s nothing more perfect than the fragrant Lillet-forward, A More Perfect Union. The atmosphere is a bit more chi chi with bartenders in vests and steel and metal framing the semi-circle bar but the vibe is still welcoming.
