While Portland summers are idyllic and sunny, and our autumns are heralded by explosions of crimson and gold across the city, our winters can get downright grim. We don’t often freeze solid like a Midwestern city, but when the sun sets in the early afternoon and the days are filled with gloomy clouds and a constant icy drip, winters can be punishing. But that’s why we have bars, especially those warm, welcoming spots with firepits and hot toddies and hearty meals to drive out the chill and the brutal malaise. Some places offer year-round comfort, while others bring festive joy with holiday pop-ups and themes. Here are some picks for our favorite cozy, wintry bars.
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Hale Pele
It might seem counterintuitive to include Oregon’s most famous (and likely best) tiki bar on a list of winter hideaways. After all, isn’t tiki—with all of its rum and juices and fruity syrups—inherently summery? But deep in the winter months, when you rarely see the sun and the nonstop gloom and rain threaten to drive you into hibernation or fleeing the Pacific Northwest, Hale Pele provides a momentary escape from the dreariness. Entirely shut off from the outside world, it’s always summer here, especially when the mai tais and flaming scorpion bowls are flowing and the crab rangoons hit the table. It manages to do all this while still being a snug, intimate little space that feels welcoming and homey. 2733 NE Broadway, halepele.com
The Sapphire Hotel
Portland’s bar and restaurant world is almost unrecognizable from what it was 20 years ago, but one constant has been the cozy little tavern tucked at the top of Hawthorne Boulevard, just past divey spots like Angelo’s and Bar of the Gods that once made up the historic “Barmuda Triangle.” That’s not to say the Sapphire Hotel hasn’t evolved over the decades. Its drink menu has kept pace with the ever-evolving cocktail scene, while its food has remained charmingly retro while adding some modern touches, offering salmon cakes, mezze platters, and gochujang wings among many other dishes. It makes for a lovely date spot in any season, but it’s at its best in winter when you can bask in the warmth of the fireplace while sipping hot drinks and noshing on bar snacks. 5008
SE Hawthorne, thesapphirehotel.com
Multnomah Whisk(e)y Library
Is there anything more wintry than a roaring fireplace, tufted leather chairs, and smoky whisky? When it comes to bars, we can’t think of anything, and that’s exactly what the Multnomah Whisk(e)y Library has been delivering since 2013. Expert bartenders can help navigate the intimidatingly large selection of dark spirits, whether you’re looking for a favorite bourbon or a new scotch. The hottest seat in the house is the table over by the vintage brick fireplace, though be warned that it’s not always lit, even in winter. Still, the hearty menu of elevated tavern staples (think steak frites, pork chops, roasted mushrooms, and meat and cheese boards) and the thick tome of spirits are sure to chase away any hibernal chills. Note that if you’re not a member, you’ll need to purchase a Hall Pass for $25 to access the Library. 1124 SW Alder, mwlpdx.com
Hey Love
For most of the year, Hey Love provides tropical oasis vibes, colorful slushies and coconut-infused gimlets paired with Machetes’ eponymous guisado-filled giant quesadillas. But each winter the bar transforms into Sleigh Love, a twinkling winter wonderland with a yuletide menu. Christmas lights and baubles dangle from the hanging plants, and garlands and candy canes line the walls. The drink selection includes the likes of eggnog slushies, mulled wine, gingerbread old-fashioneds, Cinnamon Toast Crunch espresso martinis, and allspice margaritas. 920 E Burnside, heylovepdx.com
The Slammer Tavern
One of the city’s most beloved dives, the Slammer wears its Christmas lights year-round, but during the holiday season, there are so many extra that you can probably see it from space. Don’t go in expecting elaborate holiday fare or drink specials, though—it’s really not that kind of watering hole. Instead, order a warming shot of Fireball or a stout beer, share some Jell-O shots with friends and strangers, and take in the comfort that only a friendly neighborhood bar can provide, all under the glow of thousands of twinkling colored lights. Besides, what’s more in the spirit of the holidays than escaping the family chaos for a quick, quiet drink at the local dive? 500 SE 8th,
@theslammertavern
Ringlers Annex
For decades, McMenamins has expanded its public house empire across Portland and beyond; today, there’s a good chance your neighborhood has at least one McMenamins tavern, taphouse, or music venue. Many of these places make excellent winter hangs, but the subterranean Ringlers Annex on West Burnside is a favorite for escaping the long, dreary nights of winter. That’s especially true from Black Friday through December 30, when its tiny halls are decked with festive decor for The Nightcap Before Christmas. The team busts out the Santa mugs and other cheery themed glassware and fills them with toddies, nogs, and buttered rum to warm the spirits. Other McMenamins venues hosting The Nightcap Before Christmas include the Lost Lounge in East Vancouver, the Edgefield Distillery, and the Billy Scott Bar at the Grand Lodge in Forest Grove. 303 SW 12th, mcmenamins.com
Miracle Bar
When pioneering cocktail bar Deadshot closed last year, owner Adam Robinson was quick to assure the public that the annual Christmas-themed Miracle Bar, which pops up at bars all over the world, would find a new home in Portland after five years there. Starting November 30, it will be sliding down the chimney to the spacious bar and venue White Owl Social Club. Expect a lot of wrapping paper on the walls, kitschy glassware, and holiday-spiced drinks at the most indulgently Christmasy pop-up in town, starting November 20 and running through the end of the year. 1305 SE 8th, miraclepopup.com