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What Portland lacks in size it makes up for in culture, from the number of exceptional restaurants to the laid-back cocktail scene to its incredible support of the city’s homegrown artists. And since it’s only a two-and-a-half-hour flight from L.A., it’s virtually doable as an overnight. Although, trust us: You’ll want more than that once you taste your first doughnut. 

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woodlark hotel
Courtesy of Woodlark

Where to Stay

Start your weekend trip downtown on the west bank of the Willamette River. The recently opened Woodlark is an Instagrammer’s dream, with rooms flooded with light and kitted out with blue leather, black lacquer and brass details. Don’t miss the custom-designed wallpaper, which features flora found in Portland’s Forest Park. The hotel restaurant Bullard features James Beard–nominated chef Doug Adams’s riffs on the Southern staple of “meat and three,” while java from local purveyor Good Coffee is flowing in the lobby. 

Across the street, Dossier is a favorite hotel for art and design lovers. Local painters, illustrators and printmakers contributed to the decor, an ode to the area’s lush woods and mountains. Hit up hotel restaurant Rosa Rosa right around 5:30 p.m. for a daily gratis beer and ’buch (that’s kombucha, natch). 

portland food
The Deluxe Edition 5 at Tusk by AJ Meeker

Where to Eat

Portland may be minuscule compared to L.A., but the depth and quality of the food scene is impressive. Here’s a quick rundown of our favorites by meal:

If you’re lucky enough to be here on a Saturday morning, there is no excuse not to hit up the Portland Farmers Market at Port State University. Have an incomparable fluffy biscuit and jam from Pine State Biscuits and wash it down with a vanilla hazelnut plant-based milk from aMYLK. Hungry for something heartier? Brave the line for breakfast small plates at Tasty n Alder.

If it’s sunny, have lunch outdoors at the Division location of Bollywood Theater. Order one of the thali meals (we adored the fragrant paneer makhani) that come with flaky paratha bread. Alternately, head to Coquine, located near the base of Mount Tabor. The “Perfect Lunch for Two” features a spread of dishes, a half bottle of wine, plus the restaurant’s famous chocolate chip cookies.

Probably Portland’s most famous restaurant is Ava Gene’s, a Italian spot with swoon-worthy pasta dishes such as house-made orecchiette with pork sausage, broccoli and chili. While it’s currently closed for renovations until the end of May, the team is running a fantastic red-sauce pop-up called Ava Geno’s. And be sure to hit Tusk, a Middle Eastern small-plates restaurant that sources much of its menu from the Pacific Northwest. Go with a group to sample as much as possible, including the hummus.

Lastly, you can’t discuss Portland cuisine without devoting some time to desserts, including what many consider the best ice cream and doughnuts in the country. For the former, head to Salt & Straw or Fifty Licks. For the latter, skip the touristy Voodoo Doughnut and grab a dozen at Blue Star Donuts or Pip’s Original Doughnuts. And snag a handful of Woodblock Chocolate bars as souvenirs (we’re partial to the salty ones).

Pendleton portland
Pendleton/Facebook

Where to Shop

Portland loves its local vendors. The best boutique, hands down, for locally produced goods is Tender Loving Empire, an indie record label and an artfully curated boutique selling the city’s best hometown brands. Some of our favorites include Motha’ Butta’s infused coconut butters, Sweet Honey Farmacy’s clay masks and the shop’s exclusive line of Oregon-inspired Penrose Candles.

Lovers of home goods and textiles should leave extra room in their suitcase for blankets and towels from Pendleton, the Oregon-based retailer known for its National Parks blankets ideal for picnics and Netflix binge sessions alike.

And no trip to the city is complete without paying your respects to one of the country’s greatest bookstores: Powell’s Books. The original location is in the buzzy Pearl District—walking distance from downtown—and occupies a full city block with more than 3,500 different sections.

oui wine bar portland
Oui Wine Bar/ Facebook

Where to Play

Located within the city limits is one of the nation’s largest urban forest reserves. The 5,200-acre Forest Park is open daily from 5 a.m. to 10 p.m.; check the calendar to attend a free, expert-led discovery hike. Or take it easy with a walking tour of the nearby Portland Japanese Garden, which has been dubbed the most authentic Japanese garden in the world outside of Japan.

On the other end of the spectrum, the city’s bar scene is just as quirky and delicious as you’d expect. The East Burnside neighborhood has a particularly fun stretch of spots, including the joyful cocktail lounge Hey Love and the delightfully campy bar and music venue Doug Fir Lounge. Oenophiles flock to Southeast Wine Collective, where on-site wine bar Oui! offers 60 wines by the glass, from the region and around the world.

Portland is also home to an exceptional crop of live-music venues. Dip your toe in the water by checking out one of the famed dance parties at Holocene. Dance Yourself Clean, held every second Friday, is a celebration of all things indie pop, playing music like Sylvan Esso and Charli XCX. 

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