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72 Hours in Portland, OR

Portland has its fair share of quirk going on, but quirky done right is damn appealing.


The alternative-leaning, freethinking population of Portland is destined to define the city. “Portland hipster” turns up nearly 1 million results on Google, PortlandHipster.com offers sardonic articles like “Creative Things to Do with Your Beard,” and the state’s preeminent newspaper, The Oregonian, even published a thinkpiece on the science behind becoming a hipster. The word bookends most conversations about the city and has a way of simplifying the place without really unpacking its charm. What does “hipster” even mean? Do Portland’s residents show an abnormal propensity for farmers markets? Grow their facial hair in a uniform manner? Gravitate towards a certain type of bike? Ultimately, the answers to those questions don’t seem to differ between Portland and any other young, growing metropolis. Digging a little beyond the superficial, visitors will find a free-flowing, vibrantly green city with an equal emphasis on the urban and natural. There’s also a world of beer to taste and some of America’s best affordable food, in case staying sedentary is your thing. If you have 72 hours, here are the highlights.


Where to Stay

The minimalist, industrial Ace Hotel is in the heart of downtown and nestled inside the old Clyde Hotel, which has stood just off Burnside since 1912. Ace designers retained most of the building’s original character, but also managed to squeeze in Clyde Common, a bustling small plates, fresh fare restaurant, and the ubiquitous hometown coffee joint Stumptown. For a different vibe, head across the Willamette River and try the retro converted motor lodge digs of the Jupiter Hotel (and catch an intimate concert at the attached Doug Fir Lounge). If you prefer your stay to be quirky instead of modern, try McMenamin’s Crystal Hotel, where each room is inspired by a different song or performance from an artist that played the nearby Crystal Ballroom.


Where to Eat

“No place on earth, with the exception of Paris, has done so much to influence my professional life,” American cooking legend James Beard said in reference to Portland. Andy Ricker’s Pok Pok is the city’s crown jewel, serving up Thai street food that rivals Chang Mai in a cramped, no-frills space. The Northern Thai noodle dish khao soi is a highlight, as are the fish sauce chicken wings. Creative cocktails abound as well.

In terms of big picture, the city largely jettisons fine dining in favor of fresh, hyper-local casual options. The pork belly gyro and spit-roasted porchetta are standouts at carnivorous sandwich spot Lardo, while the off-menu, late-night-only burger at underground izakaya Biwa has bred fervor among locals. For breakfast, order up a gravy-smothered, bacon-topped Reggie sandwich at Pine State Biscuits or embrace your inner-NYC leanings with a house-made bagel at Kenny and Zuke’s. Portland’s coffee bears mentioning as well, with a bevy of top-notch third-wave options scattered throughout the city. Almost every resident seems to have their own opinion, but my personal favorite is Ristretto Roasters, with its friendly attitude and constantly updated selection. Heart and local legend Stumptown are also recommended.


What to Do

Oregon is #1 in the US in breweries per capita, so uncovering that part of the city could be considered necessary cultural research for a visitor. Deschutes is one of Oregon’s biggest craft beer makers and they do their experimental, small batch brewing in Portland. Visitors can get a fresh-out-of-the-tank pint of things like Peated Scotch Ale, Munich IPA, or Fresh Hop Mirror Pond Pale Ale. The wide-open, airy 10 Barrel brewpub is perfect for a sunny day and the award-winning Ninkasi Brewery deserves a taste too. A 10-minute drive from downtown Portland will take you to Washington Park, which includes a zoo, the renowned International Rose Test Garden and a host of museums, but also trails that feel like a legitimate nature escape. Portland houses a great number of music venues, but the finest might be downtown’s Crystal Ballroom. If you catch a show, be ready to dance on the century-old venue’s “floating floor” that pitches up and down with the crowd.


Venture Out

Portland stands alone just fine as a metropolis, but the city’s appeal is supercharged upon survey of the surrounding nature. A beautiful 2.5-hour drive through the Willamette National Forest and up the Cascades will get you to the McKenzie River Trail, a stunning single-track that soldiers past waterfalls, old growth forests and hot springs. Continue over the mountains to the outdoor utopia of Bend, which is a runner, golfer, and biker’s paradise. If you prefer (rocky) beach instead of mountains, head west and explore Tillamook, Newport, Cannon Beach or any other number of towns along the Oregon coast. Astoria, best known for its role as the setting of The Goonies, is less than two hours from Portland and perhaps the gem of the coast.

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