Oregon’s hippest city.
Portland Cool-Hunting
Credit: Cedric Angeles

With a hip arts scene, great restaurants and bars, and an eco-conscious soul, Portland, Oregon is an indie utopia. It’s that rare kind of city where you can find everything in one place, and what you can’t is just beyond its borders: the ocean and mountains. Come here to bask in its vibrant downtown, strike out into nature, or just get to know some of the local characters—chances are, you’ll be glad you did.

Alberta Arts District

This curious strip of avant-garde art galleries, funky boutiques, and affordable ethnic eateries has recently sprung up in an otherwise quiet section of northeast Portland.

Doug Fir

Part of the retro-hip Jupiter Hotel, this dark and quirkily furnished music club and lounge has been one of the key cultivators of Portland’s white-hot indie-music scene. A steady mix of rock and alternative bands is booked here, and quite a few of them (including Spoon and The Decemberists) have gone on to stardom. Log walls and ceilings, kitschy, futuristic lighting, and low-slung 50’s-era tables and lounge chairs impart a Jetsons-meets-Paul Bunyan aesthetic.

Simpatica Dining Hall

Located in an art-lined basement with communal tables in a building east of the Willamette River, this restaurant sprouted from a charcuterie and butcher shop called Viande Meats and Sausage and focuses on comfort food crafted from local, seasonal ingredients. There's a Friday and Saturday dinner, which changes daily and has four courses, which might include slow-cooked Wagyu beef brisket with spoonbread or seared scallop spiedini with Cara Cara oranges. Sunday brunch is a la carte, and the menu changes frequently, but waffles endure. They’re vessels for toppings both sweet (dried fruits and Chantilly cream) and savory (fried chicken).

Ace Hotel

This hotel is pure Portland: creative, authentic, irreverent. Rooms in the revamped 1912 hotel are decorated with murals and fitted with vintage claw-foot tubs; bedside tables are fashioned from secondhand tomes (the famous Powell’s Books is just down the block). It’s no wonder bands on tour like to stay here: there are in-room turntables and vintage LP’s, and guitar strings for sale at the front desk. Staff dressed in Nom de Guerre–conceived ensembles (button-down shirts, crisp Dickies pants) are as cool as the surroundings.

Voodoo Doughnut

This quirky, kitchy shop is known for crazy flavors and long lines. Known for their insatiable maple bacon bars and Cap N' Crunch donuts around the clock, they also offer vegan varieties.