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1. Hale Pele
2733 NE Broadway, 503-662-8454, halepele.com. 4 pm–midnight daily.
Step into the dark and moody confines of one of America’s best tiki bars, right here in Portland. Adorned with glowing puffer fish, bamboo and tiki totems to conjure the feeling of being in a beachside hut, Hale Pele is the perfect escape from the winter gloom. You can indulge in boozy rum-laden classics like a mai tai or a Suffering Bastard while watching the bartenders concoct lively mixologist pyrotechnics to a soundtrack of exotic lounge music and the occasional simulated thunderstorm. Cocktails for two are offered, and the Volcano Bowl comes billowing fire and smoke for a true spectacle.
2. Sit Tite
6214 N Interstate Ave., sit-tite.com. 4 pm–midnight Sunday–Thursday, 4 pm–2 am Friday–Saturday.
Sit Tite is a low-key neighborhood bar that serves the kind of unpretentious food you find at the numerous Italian joints spread across New Jersey and Long Island. In a nod to our nostalgia- and meme-obsessed culture, Sit Tite comes with Sopranos references aplenty, from the name itself to the cocktail menu. We adored the Commendatori ($15), a nod to the retrending espresso martini that distinguished itself with Amaro Averna, salt and frothy cold brew, and the Smoke Out Confessional ($13), with its inventive take on a Hemingway daiquiri distinguished by mezcal and elderflower.
3. John’s Marketplace–Hall
3700 SW Hall Blvd., Beaverton, 503-747-2739, johnsmarketplace.com. 11 am–9 pm daily.
Formerly parched downtown Beaverton has been swimming in beer for the past few years. The area has outlets for two breweries as well as a handful of beer bars. Joining the perennial beerfest is John’s Marketplace, which opened its third location on the edge of Old Town. Most everyone is here for a pint paired with the well-charred, quarter-pound smash burgers, including beer nerds sporting branded swag and moms clad in Lululemon with children in tow. Join them under the beer banners in the taproom before perusing the bottle shop for something special to take home.
4. The Houston Blacklight
2100 SE Clinton St., 503-477-4738, thehoustonblacklight.com. 4–11 pm Monday–Thursday, 4 pm–midnight Friday, 10 am–midnight Saturday, 10 am–11 pm Sunday.
The Houston Blacklight works because it does something a lot of people forget to do when they open a bar in this city: It feels like a place made for Portland, not shuttled in from somewhere else. It’s not a faux dive, and it’s not swanky or elevated; it’s just a goofy fun thing with wildly juicy cocktails and some solid bar bites. Embrace the vibe by ordering a slushie: the turquoise Thot Experiment combined with whatever other flavor is available. Also watch for Many Things Cannot Fly to return to the menu. The blackberry gin concoction is served in a speckled-blue dinosaur egg with a toy dino riding the straw.
5. Division Winemaking Co. at the Wine Yard
2005 SE 8th Ave., 503-208-2061, thewineyardpdx.com. 2–6:30 pm daily.
A tasting here includes some of the finest examples of Oregon pinot noir and chardonnay alongside trendier styles like gamay, pet nat, and orange wine. The coolest part is that all of Division’s wines are made in the same building that houses its hip and sun-washed tasting room. It is also an urban winery, with others in walking distance, meaning you can get a true winery experience without trekking out to the Willamette Valley.