Nightlife in Portland, Oregon

In the 1800s, it was a horse and buggy stop on a dirt road. Then it became a tavern called Max Alibi. In 1947, new owners took over, keeping the Alibi name and transforming the space into a Hawaiian-inspired hangout serving. Today the tropical drinks are still flowing, but the main attraction is that the Alibi serves up the city’s best karaoke party every night of the week. Watch as shy first-timers and old pros take the stage and belt out the hits, and feel the hundred-plus year history of pioneers, bar flies and wannabe singers who’ve imbibed here before you.

Walking into this downtown Portland institution is a bit like traveling back in time. Career waiters in crisp white shirts and black ties greet you with manners from another era. Everyone’s drinking martinis and slurping oysters. And it feels like you might find Humphrey Bogart tossing drinks back in a corner for good reason – he used to be a regular here. The bar’s history dates all the way back to 1892, but today it’s as popular as ever thanks to its signature old-school charm and stiff drinks. It’s also got one of the best happy hour menus in town: score classic cocktails like Sidecars, Whiskey Sours, and Spanish Coffees at a discount, and order oysters, cheeseburgers, Dungeness crab dip, and popcorn crawfish from the $7.95-or-less HH food menu.

Shelves with 1,500 bottles of booze accessed by rolling brass ladders line the walls of Portland’s most refined cocktail den. But there’s no reason to be intimidated – even if you don’t know the first thing about whiskey. Settle into one of the plush leather sofas or club chairs and cozy up to the fireplace. Order from the sure-to-please cocktail menu (yes, there are drinks made with gin, vodka, and rum too), or let MWL’s very knowledgeable and totally pretense-free bartenders guide you towards your new favorite custom cocktail. 

Portland has more than its fair share of endearingly grungy dive bars, but The Slammer may be its best-loved. The former cop bar in the southeast industrial neighborhood has changed very little as its surroundings have become more and more hipster-fied. Don’t come here expecting craft cocktails – you’re best off ordering a no-frills beer or a vodka tonic at most. There’s always a festive vibe due to a jolly crowd of regulars and a ceiling decked out in thousands of colorful Christmas lights blazing every night of the year.

Portland has earned its title as one of the country’s top beer cities – it seems like there’s a craft brewery on nearly every block, and indeed it has one of the highest rates of breweries per capita of any city in the world. But the best bar for sampling Oregon’s many craft beers in one place is the Loyal Legion in inner southeast. Choose from a whopping 99 beers on tap, all craft beers made within the state. Whether you fancy IPAs, lagers, sours, stouts, ciders, hard kombuchas, saisons, or hazy brews, you know you’ll find it here.

Is Portland the country’s strip club capital? The claim that the Rose City has the most strip clubs per capita of anywhere in the U.S. may or may not be accurate, but there’s no doubt that it has every brand of exotic entertainment. There are strip clubs known for tattooed women and heavy metal soundtracks (Lucky Devil Lounge), and others where muscled-and-oiled gay male dancers take the stage (Silverado and Stag). There are clubs with good food from steak (Acropolis Steakhouse) and vegan fare (Casa Diablo). But Mary’s still reigns supreme as the most classic Portland nudie destination. The downtown Portland mainstay opened in 1945 as a piano bar catering to merchant marines. Decades later, the beloved club still lures in locals and visitors alike with its scrappy Portland charm. It’s dark, intimate, and black velvet paintings fill the walls. Order a drink from the all-female bar staff, watch the ladies come on stage and select their own soundtracks from an old jukebox, and take in one of Portland’s most storied destinations. 

Spirit of ’77 is proof that sports bars need not be dark, stuffy dens of hyper-masculinity. Named for the year of the Portland Trail Blazers’ National Basketball League championship, the space is modern, bright and airy, with an enormous projection screen, four TVs, and games like foosball, pinball, and buzzer-beater basketball. The Lloyd District location is mere blocks from the Moda Center coliseum, home to the NBA’s Portland Trail Blazers, making it the ideal destination for pre- and post-game drinks and flirtations. 

A fog machine and soundtrack of rain and thunder set the scene at Hale Pele, which is often lauded as one of the country’s best tiki bars. Fresh juices, premium spirits, and house-made syrups elevate classic tiki drinks like Mai Tais that are often cloyingly sweet in the hands of lesser mixologists. Order one for yourself, or gather a few friends to sip a communal cocktail like the Volcano Bowl, served complete with fresh flowers and a column of flames. Visit the bar between 4 and 6 p.m. any day of the week for $6 tiki drinks and cheap eats.

If the words “wine bar” conjure up stuffy and serious spaces with overpriced bottles, this urban winery will make you rethink them. The immense space – a former auto body shop filled with light and dripping with verdant plants – functions as a working winery, taproom, restaurant and venue for weddings and other events. The wine is poured from kegs, not bottles, which makes the process more friendly to the environment as well as your wallet. Sip Coopers Hall’s own wines, or sample guest taps from wineries around the Pacific Northwest.

Throw a stone in Stumptown and you’re likely to hit a sleepy dive bar. High-energy night clubs with chest-thumping music beckoning you out to the dance floor are fewer and far between. But Holocene has been throwing the best dance parties in town for fifteen years and hasn’t slowed down. Check their calendar for an eclectic mix of events: they’ve got dance parties where they blast everything from retro 80s/90s tunes to indie pop, and SLAY, a regular hip hop night for LGBTQ+, people of color, and the open-minded party people who support them. 

Come to Expatriate for the globetrotting selection of stellar cocktails, sakes, wine, and beer…but stay for the snacks. That’s because superstar chef Naomi Pomeroy — of Top Chef Masters fame, as well as fine-dining Beast restaurant across the street – is behind the menu of deeply satisfying drinking snacks. Order local legend James Beard’s famous onion & butter sandwich for a mere $6. Or, take your taste buds on an Asian-inspired culinary tour with favorites like Burmese Coconut Noodles with ramen egg, Laotian tuna belly tacos, or the reimagined Expatriate Nachos, wonton chips topped with Thai chili cheese sauce and spicy lemongrass beef.

This French-inspired neighborhood bar and bistro strikes just the right chord for rendezvous of a romantic nature. With its tufted black leather banquets, gorgeous cobalt blue surfaces, and chic graphic wallpaper, it’s cozy without being claustrophobic, sexy without being overt. The eclectic bar program means your date will be happy no matter if they’re in the mood for Champagne, Belgian beer, local wine or beer. And if the night goes well, stay and order one of Le Moule’s sultry and shareable plates like oysters on the half shell or steamed mussels and fries.

Drive the busy stretch of Burnside just east of the river and you’ll spot the Doug Fir, a PDX music mainstay with a style they describe as a “Twin Peaks meets The Jetsons urban ski lodge.” It will feel like you’re in a log cabin, Zen garden, modernist home, or a 1950s diner depending on what room you’re in. But the main attraction is the live music in the 1970s-style rec room basement, where big-name bands and local favorites (which are sometimes one and the same) play every night of the week.

When the rain subsides in Portland, locals head to the rooftop at Revolution Hall to soak up some sun and take in the unbeatable 360-degree views. A former high school, the top of this live music venue is the perfect perch for looking out over the Southeast Industrial neighborhood, downtown Portland, and the beautiful West Hills while sipping cocktails or local beers and wines. Got kids? Minors are allowed on the roof deck nightly until 7 p.m. If not, watch the sun set and then head downstairs to catch one of Revolution Hall’s concerts, thought-provoking lectures, or film screenings in the beautifully restored auditorium. 

“Have a pint, change the world.” That’s the motto of this community-focused North Portland pub that works to support local nonprofits. Here’s how it works: after covering their operating expenses and contingency savings, the OPH gives all of its profits to a number of nonprofit partners in the area whose missions range from arts for underprivileged kids to animal welfare, the environment, education scholarships, and more. That means that part of every pint, cocktail, and burger you order there goes to the greater good in the community. Cheers to totally effortless (and delicious) philanthropy!