Portland has a reputation that precedes it. Oregon’s most populated city is associated in the national imagination with both hipsters and hippies, crowded as much with tattoos as Birkenstocks.

But while much of Portland lives up to the stereotype, the city is also incredibly diverse in its urban offerings, a trait best exemplified through its nightlife.

An evening in Portland offers everything from swanky, dimly lit cocktail lounges to dingy dives to raucous music clubs. Connecting all of them is Portland’s oft-lampooned but seriously followed modus operandi: Individuality reigns supreme.

Multnomah Whiskey Library

Apartment living defines De Pijp. The residential buildings, which date to the 1900s, are filled with long, narrow units that have windows only in the front and back. Aside from some renovated buildings, most do not have elevators.

According to Joanknecht, renovated units go for 7,000 euros (US$7,970) per square meter, putting the price range at €280,000 to €560,000.

Doug Fir Lounge

With 14 years on the Portland scene, this popular log-cabin-esque music venue in the centrally located East Burnside neighborhood, adjacent to the Jupiter Hotel, knows exactly what works. By its own description, Doug Fir’s interior design is “Twin Peaks meets the Jetsons,” which, in a very Portland way, works spectacularly. The focus rests squarely on the music; most anywhere you are in the place, you can see the stage. The lounge’s designers commission a unique poster to be made by a local artist for each show. Recently the place underwent a mini-revamp, with a new food menu focused on local ingredients and vegan fare, more advanced cocktails, and the addition of a custom photo booth.

Mississippi Studios

If there is anything one can expect from a former Baptist church turned recording studio turned concert venue, it is variety. This late-night legend, located on the always-hopping Mississippi Avenue, puts on some of the best and most intimate shows in town, from garage rock to indie folk to reggae (tickets from $5 to $20). The joint next door, Bar Bar, is also part of the attraction, with people often going between the two spots. At Bar Bar, there is great patio space and a hidden garden. It also boasts some of the best burgers in the city.

The Solo Club

For a more subdued experience, snag a table and sip one of the expertly designed cocktails at this bilevel, European-style drinking den in northwest Portland. It is known for its amaro-based libations, such as the fernet and cola, or cava served with your choice of amaro. The carefully crafted food menu, with seared diver scallops and lamb meatballs, is also wonderful, as are the pastries and coffee. Its popular patio is a goodspot for enjoying “coolers”—combos of beer, soda, and bubbly wine.


Nestled in the Alberta Arts District is this slightly surreal cocktail lounge. Consider the Hollygrove: Pierre Ferrand 1840 cognac, yellow chartreuse, lemon, foreign palm sugar, fresh orgeat, and blue Curaçao. Or try the Alibi: Pueblo Viejo Blanco tequila, fresh lime, hibiscus, local honey, ginger, and prickly pear cactus. Bartenders here are also known to customize drinks based on tastes. Not to be missed, though, are the Asian-inspired “drinking snacks,” out of the mind of Naomi Pomeroy, the 2014 James Beard winner for Best Chef Northwest. We’re talking about Laotian Tacos, with toasted coconut, tuna belly, nectarine, lime, chili, dried shrimp, candied peanuts, and fish sauce; Burmese Coconut Noodles with chicken; and more.

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