Located at the heart of the city in the vibrant Old Town Chinatown neighborhood, Portland’s Entertainment District is a go-to spot for late-night frivolity, whether it’s live DJs, tasty cocktails or rowdy dance floors. To maximize fun, visit on Friday and Saturday nights after 10 p.m. when the blocks between W. Burnside St., N.W. Everett St., N.W. Second Ave. and N.W. Fourth Ave. are closed to cars, transforming the area into a pedestrian-friendly party zone.
Set within walking distance of a number of popular nighttime destinations, the Society Hotel, a newly revived 19th century sailor’s boarding house, provides a perfect weekend basecamp. Fuel up for your evening adventures at Alexis, an authentic Greek restaurant that serves heart-warming fare on classic blue and white checked tablecloths. (If you’re lucky, you’ll catch some traditional belly dancing.)
To pair your bites with local brews, grab a slice at Old Town Pizza and Brewing and sample the potent Shanghai’d IPA. Located in the historic Merchant Building, the space is rumored to be haunted.
Looking for a laid-back vibe? Check out the affable gay bar The Fox and Hounds. If you’re ready to groove, head to Fortune, a hip lounge with an emphasis on good food, great drinks and top-notch DJs, or check out Tube for a grittier vibe and more great beats in a unique space.
For the full-blown dance club experience, CC Slaughters and Dirty Nightclub are always bustling on weekends and often feature energetic live DJs. If you prefer a more down-and-dirty, rock-and-roll vibe, swing by Dixie Tavern, where servers are known to dance on the bar and brave revelers are sometimes invited to join in.
Dancing-averse night owls have plenty of options too: Check out the “all request” dueling pianos at the Barrel Room or catch a cabaret performance courtesy of the legendary Darcelle XV and friends, who have been delighting audiences with nightly drag shows since 1967. If you prefer to provide your own entertainment, the Boiler Room is a hot spot for late-night karaoke. Be warned: The waiting list to sing can get lengthy, but the crowd is always lively and supportive.
When the inevitable late-night munchies strike, you’ll find several options near the Entertainment District. At Asian-influenced Portland City Grill, kung pao calamari and chili-ginger pork ribs are served until 1 a.m. on weekends. Queue up for your obligatory Voodoo Doughnut conveniently open 24 hours, or try a lower-profile fried treat from Donut Byte Labs (open until 1 a.m. Friday and Saturday).