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Winter is when Portland’s coziest bars and lounges truly come into their own—full of warm lights, energized people, and seasonal spirits. As we hurtle toward the holidays, it’s the perfect time to meet up with those you care about to enjoy a classy cocktail together. Even better: The rise of high-quality mocktails means the fun doesn’t have to stop even come Dry January. So join us on a winter cocktail safari, as we hunt down what’s being stirred, shaken and served to celebrate the season.
Driftwood Room at Hotel deLuxe
The Hotel deLuxe’s Driftwood Room is an homage to Old Hollywood glamour, a shadowy lounge that feels both timelessly elegant and like somewhere your grandmother would have gone out for a fine evening. The Driftwood Room features two highlights, the champagne-based Elizabeth Taylor, and its absinthe fountain service. Brut champagne is served with créme de violette as a dark floral-candied wink in homage to the dame’s nearly purple blue eyes. The Goose Hollow hotel lounge’s French absinthe fountain is a luxurious taste of a once-forbidden delicacy that now harks back to a century-plus of rebelliously refined decadence. The works come with sugar and a selection of eight different absinthes poured at two drops per second, adding a sense of anticipation to the fun.
729 SW 15th Ave., 503-820–2076, hoteldeluxe.com/dining/driftwood-room
Fortune
The Sentinel Hotel’s vegan restaurant and jazz lounge Fortune features a range of cocktails with fresh ingredients fit for all liquor profiles. As with the food menu, Fortune’s drink program uses fresh plant-based ingredients to give cocktails an extra sharp crispness. Whether you’re looking for something that pairs well with dinner and an evening of jazz—or something that stands out on its own—it seems like Fortune will be in your favor.
614 SW 11th Ave., fortune.bar
Conspirators’ Coffee Lounge
Plenty of people will probably do Halloween-on-Christmas at Raven’s Manor, but if you want to be transported from the holiday doldrums into a quieter immersive experience, you can still sneak into the company’s hidden speakeasy tucked within the walls of Black Cat Frozen Custard. Conspirators’ Coffee Lounge is only accessible via password given at the custard counter. From there, guests slip into what feels like the sprawling study of an Old World mansion. There’s a main floor with comfy seating, and a cozy second-story alcove, to transport you away from street noise and modern troubles.
133 SW 2nd Ave., #100, instagram.com/conspiratorscoffeelounge
Dirty Pretty
The trendy cocktail lounge Dirty Pretty draws in a younger crowd, but the East Burnside bar’s menu is so inventive that everyone should experience it. The star draw is its Taco Bell-inspired food and drinks, but the other offerings are also more than Instagram confections. The menu can shift seasonally, but expect gorgeous colors, a photogenic garnish or flourish, and some dangerously sippable recipes.
638 E Burnside St., 503-841-5253, dirtyprettypdx.com
Hey Love
Hey Love is wrapped in tropical vine plants year round, but in December the Jupiter Next’s lobby lounge cranks up the Christmas spirit with its Sleigh Love programming. This place packs enough holiday decorations from floor to ceiling to give Peacock Lane a run for its money. Big fans of Santa and winter light displays will want to set some time aside for a photo op, but Hey Love’s cocktails and slushies will offer tropical reprieve from seasonal affective disorder.
920 E Burnside St., 503-206-6223, heylovepdx.com
82 Acres
Abbey Road Farm’s bar and restaurant is an easy stroll down the street from Clinton Street Theater. Two standout items on the winter cocktail menu are the Nordic Nectar and the Last Word. The former uses lemon and honey to balance out the taste of Krogstad Aquavit—the Scandinavian spirit’s herbaceous taste is traditionally associated with cold weather and the holidays. The latter blends Beefeater gin and trendy green chartreuse (rarer nowadays due to the monks who make it no longer bowing to market demand), Luxardo Maraschino Liqueur, lime and brandied cherry made from produce grown at Abbey Road Farm.
2032 SE Clinton St., 503-200-5787, 82acrespdx.com
Afterlife
The shadowy Hawthorne cocktail lounge Afterlife has attracted a community of dance enthusiasts, local DJs, and movie buffs who need to digest what they saw at the Bagdad Theater after the McMenamins concession stand wraps for the night. If you’re looking to go nonalcoholic for the evening, this place won’t disappoint—try the refreshing Mind & Body blend of pineapple and oat milk to ease down gently into the cold dark night without feeling let down.
3632 SE Hawthorne Blvd., afterlifepdx.bar
My-O-My
It might seem counterintuitive to order slushies in winter, but My-O-My’s menu of tropical crushed-ice cocktails can actually help cool customers down if body heat and the Sumner neighborhood bar’s fireplaces happen to work too well together. There are also plenty of winter beverage options available, such as the Gung-Ho cocktail featuring Wild Turkey rye, Ancho Reyes chile liqueur, cinnamon syrup, cardamom and lemon.
8627 NE Sandy Blvd., 971-865-5994, myomypdx.com
Aurora
Maybe you’re at Portland International Airport picking someone up, or maybe your ride is late. Either way, you’re not on the same side of the security check as the Hollywood Theatre’s microcinema and you don’t want to take laps at Cascade Station. Loyal Legion’s semi-secret speakeasy Aurora is awash in LED rainbow hues with colorfully tinted windows to liven up views of the tarmac. It won’t take long for you to find it, but once you do, it’s the closest thing to a rave the FAA will allow. And if you really do want to make a special trip to have a cocktail at the airport this winter, hey, we won’t judge.
7000 NE Airport Way, instagram.com/drinkataurora
Public Leisure House
The St. Johns cocktail lounge and low-key event space Public Leisure House offers a gathering place as casual as the neighborhood’s many breweries and beer halls. PLH’s winter cocktail menu veers between sunny escapism and holiday cheer, but one of the more sparkling standouts is the Old Fashioned Brûlée, a mix of cinnamon simple syrup with Rittenhouse rye and a brûléed orange slice sweet and dark as a mid-February night.
8002 N Lombard St., 503-289-7606, leisurepublichouse.com
Havalina
Don’t confuse the St. Johns craft cocktail purveyor Havalina with its Cully neighborhood homonym and Indigenous food spot Javelina. Both are worth a visit, but Ezra Holbrook’s lounge has livened up its corner of North Lombard’s northern strip with live music and food cart space, along with a competitively affordable, seasonally shifting cocktail menu. Apple cider will be big again this year, as previewed with the apple Manhattan earlier this fall.
8927 N Lombard St., 971-217-7727, havalinapdx.com
Oregon Winter is Willamette Week’s annual winter activity magazine. It is free and can be found all over Portland beginning Friday, November 21, 2025. Find your free copy at one of the locations noted here, before they all get picked up.
