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Three Perfect Days: Portland

America’s hipster capital is home to world-class dining, dozens of microbreweries, a quirky arts scene and some of the most beautiful parks and natural landscapes in the country. Other than that, it’s pretty nice here.

Author Justin Goldman

A few of the 11 bridges that cross the Willamette River in downtown Portland / Daniel Cronin

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DAY TWO | You shake yourself awake, relaxing for a few minutes in the boxing robe you find in the closet, before stumbling outside and around the corner, past a sculpture made of intertwined kids’ bicycles, to Tasty n Alder. You take a seat at the impressively stocked bar and order a couple of proven restoratives: a Kentucky Peach—basically a bellini with a splash of bourbon—and a Hangtown Fry, an oyster and bacon frittata served with a huge buttermilk biscuit.

Substantially recovered, you stroll over to the Portland Saturday Market, a sprawl of artists’ stalls, food carts and craft vendors stretching along the Willamette River waterfront and under the Burnside Bridge. You skirt a large crowd circled around a semi-competent juggler and snake through booths selling handmade jewelry, Oregon-themed clothing and images of Mount Hood rendered in every possible medium. It’s a bit too crowded to really stretch your legs here, though, so you wander along the South Park Blocks, a stretch of greenery where you find lush oak and maple trees, roses (naturally), statues of Teddy Roosevelt and Abraham Lincoln, and a wedding party snapping photos.

You stop to stare up at the Portlandia statue, a trident-bearing woman that, at 36 feet tall, is the second largest hammered-copper statue in America (after some French lady in New York). You’re surprised to find the sun starting to feel a little too hot, so you head a couple blocks west for respite at the Portland Art Museum, where you while away an hour or so among the killer whale masks and intricately beaded bags in the Native American art gallery. The feather-bedecked Raven to Sun Transformation Costume makes you want to go on a vision quest.

After wolfing down a couple of carnitas tacos at another fine food cart, La Jarochita, it’s check-in time at your second hotel, the Sentinel. The 100-year-old building—a National Historical Landmark and a setting for Van Sant’s My Own Private Idaho—reopened this spring after a $6 million renovation, and its design offers a blend of past (the green leather armchairs and rugged wood tables in the lobby recall Oregon’s legacy as a timber capital) and future (robot sculptures on the facade). A nice touch is the typewriter in the lobby, where guests can tap out comments. You start to type “IPDX,” but there’s no heart symbol on the machine, so you head upstairs and sack out on your enormous bed for an afternoon nap.

You wake feeling refreshed and hop a bus across the Morrison Bridge to sample the wares at Enso Urban Winery. You take a seat in the facility’s airy, industrial tasting room and order a flight of red wines. The Pacific Northwest has established itself as one of the best wine-growing regions in America, and the bold reds at Enso help explain why. “Oregon’s on the same parallel as Burgundy,” says bartender Henry Jinings. “The growing conditions are ideal.”

Whistle whetted, you take a cab to Southeast Division Street, Portland’s flourishing restaurant row. Your destination is Pok Pok, one of America’s most revered Thai restaurants. The hostess tells you there’s an hour wait for a table, so you put your name on the list and cross the street to its sister bar, Whiskey Soda Lounge, where you sit in the tented patio and order chili-flecked Ike’s Vietnamese Fish Sauce Wings (a highlight from the Pok Pok menu). Just as you finish washing them down with a tamarind whiskey sour, a waitress informs you that your table is ready.

Pok Pok’s James Beard Award–winning chef, Andy Ricker, derives his menu from the cuisine of northern Thailand (no Pad Thai here). You sample a spicy, sour, wonderfully fresh papaya Pok Pok salad; the hoi thawt, a light crepe stuffed with eggs and fresh mussels; and kaeng hang leh, an outrageously rich pork curry with Burmese spices. Nothing tastes like anything else on the table, or anything else you’ve eaten anywhere. Forget sampling—you plow through it all like it’s the last meal you’ll ever eat.

After dinner, the simple act of standing up poses a challenge, but you somehow manage to hail a cab and head to an eastside institution, the LaurelThirst Public House, one of the best places around to catch local folk and country acts. Tonight they’re hosting a Grateful Dead cover band, who’ve attracted an audience that consists of flailing college kids and old hippies, among them a white-bearded man in a tie-dyed shirt bearing a large wooden walking stick who looks like a Haight-Ashbury version of Gandalf.

You’re close to toast by the time you get back downtown, but you’ve got a reservation at the exclusive Multnomah Whiskey Library, where you sit in a leather-padded booth and take in the high-ceilinged brick barroom. On one side hang portraits of famed whiskey makers, including George Washington, and on the other is the extensive “library”—the bar has old-fashioned ladders to reach the upper shelves—of whiskeys. You consider one of the cocktails, which are mixed tableside, but opt instead for an Old Rip Van Winkle 10 Year bourbon, neat. Your server gives an approving nod, and you close your evening sipping one of the best spirits on the planet.

7 Responses to “Three Perfect Days: Portland”

  1. Cara Tobias Says:
    July 1st, 2014 at 6:52 pm

    And there is SO much more to do in the Portland area in a week! Regarding fashion , “Project Runway ” winners and select vintage that compelled a white house visitor to fly in to buy her gown for the inaugural.And then there is NIKE world campus on the way to one of the best loved coasts in the world. Thanks for the LOVE!

  2. Sue lang Says:
    July 16th, 2014 at 7:21 am

    Thank you

  3. Cornelius Cornhagen Says:
    July 29th, 2014 at 12:21 pm

    The second-person narrative is kind of creepy. Are they ordering me to do this stuff? Are they presciently forecasting my future? Is the author having an out-of-body experience?

  4. Mary Says:
    August 23rd, 2014 at 6:51 pm

    Good advice if you’re a rich alcoholic inclined to get a tattoo. Pretty small demographic for this article.

  5. Julee Jackson Says:
    September 1st, 2014 at 10:30 am

    I was born and raised in Portland and vicinity. I now live in Florida. Returning to Portland for a few days vacation and LOVED this article. Will check out most of places this article refers to. Thanks, downloading it now. Having trouble finding a way to download the iPhone app though.

  6. Nonya Says:
    November 6th, 2014 at 7:56 pm

    Where are these world class restaurants you speak about? I can’t find good food anywhere when in the area. It rains non stop, people stare at you if you wear clothing other than fleece and the down town has zero nightlife. One of the worst cities ever been to. No culture, no food, no entertainment and not a whole lot of sunshine. PASS!

  7. Karen Nelson Says:
    October 31st, 2015 at 2:18 am

    Soggy Portland is cold & depressing. It also has snowy winters. But some people like that. I guess all the rain keeps it green. Bring your Birkinstocks, woolen socks, down vest, and extra Vitamin D!

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