Three Perfect Days: Portland
Portland has MORE than its share of nicknames—Stumptown, Brewvana, Bridgetown, PDX, Rip City, the City of Roses—but odds are you haven’t heard many of them. Despite being home to iconic indie artists like Gus Van Sant and Elliott Smith, not to mention some of the best microbreweries in the world, to most people Portland is just a small Pacific Northwest city that gets a lot of rain.
Recently, though—due in part to “Portlandia,” the IFC comedy that lovingly lampoons hipster culture—Portland’s public profile has been on the rise. The city (motto: “Keep Portland Weird”) has become a magnet for creative types, drawn to its bookstores, record shops, music venues, public artworks and tattoo parlors. As Fred Armisen puts it on “Portlandia,” it’s “a city where young people go to retire.”
But you don’t have to be a clued-in 20-something to enjoy Portland. Thick with public parks and surrounded by pristine forests and mountains, it’s a dream locale for outdoors enthusiasts. The damp climate and proximity to first-rate farms also provide the thriving restaurant, winery and brewery scene with an abundance of fresh ingredients. Those seeking traditional cultural outlets, meanwhile, can avail themselves of Portland’s museums and art galleries, many of which have taken over industrial spaces across the city.
Today, the national media’s appreciation for the city has become so ardent that locals refer to the blitz of coverage as “stalking.” But Portlanders remain exceedingly friendly—you shouldn’t be surprised if one offers you a ride into town from the airport and regales you with recommendations the whole way. People are especially cheery in the summer, when the clouds part, brewpub patios hum, and cycling becomes the only acceptable form of transportation, be it to an art fair or an organic grocery.
DAY ONE | You wake up at the Ace Hotel, a boutique property in Portland’s revitalized West End neighborhood, and immediately rue your lack of skinny jeans. The Ace is quintessential Portland: Leonard Cohen lyrics painted on the walls, a photo booth in the lobby, a record player in your room. It sometimes feels a bit too cool for school—but you’d probably adopt this attitude too if Gus Van Sant had filmed Drugstore Cowboy in your house.
You’re feeling coffee and doughnuts this morning, in part because Portland does those two things better than anywhere else. On your way out the door, you grab a latte from Stumptown Coffee Roasters, then take a short walk down Burnside, the street that separates Portland’s north and south sides. Here you find Voodoo Doughnut, a legendary line-around-the-block fried-dough joint, where you pound down a bacon maple bar and the store’s eponymous confection, a chocolate-covered voodoo doll with raspberry jelly innards and a pretzel stick protruding from its chest.
Somewhat overfed, you take a vigorous two-mile stroll over to Washington Park, in the West Hills, where you are instantly soothed by the sculpted flora of the Portland Japanese Garden. Transfixed, you half walk, half float past the koi pond and the stone garden and onto the back porch of the pavilion, where a resplendent view of Mount Fuji—er, Mount Hood—causes you to catch your breath.
From here, it’s a few flights of stone stairs down to the International Rose Test Garden. Founded in 1924, this is the oldest continually operating public rose garden in America, and quite possibly the prettiest. You wander through a maze of multicolored hedgerows, admiring the apparently endless variety of Portland’s signature flower—Betty Boops, Scarborough Fairs, Blueberry Hills. You’d stop to smell them, but with more than 10,000 roses in the garden, that would take all summer.
You’ve worked up an appetite by the time you get back downtown. Fortunately, the city center is Foodcartlandia, its corners overrun with vendors offering everything from schnitzel to paleo fare. You step up to Nong’s Khao Man Gai and order the signature dish, a Thai street creation comprising rice and poached chicken topped with a hot sauce that torches your taste buds. They die happy.
After lunch, you make a pilgrimage to Powell’s City of Books. The world’s largest independent bookstore, Powell’s takes up an entire city block and is so cavernous that the information desks provide maps. You head to the fourth-floor rare book room, where used book buyer Kirsten Berg shows you a copy of D-Day narrative The Longest Day that includes an inscription from the author to Eleanor Roosevelt. “I love the things people stick in books,” she says. The volume’s price tag ($2,000) is prohibitive, so you pick up a copy of local author Katherine Dunn’s fantastically weird novel Geek Love and make for the cash register.
Your mini shopping spree isn’t over yet: You’re going to need some vinyl to spin on that hotel turntable. As it happens, there are two excellent record shops within three blocks of you: Everyday Music, where you pick up a copy of the late, great Elliott Smith’s self-titled album, and Jackpot Records, where you get the new record from local indie band Blind Pilot. Arturo Diaz, the store’s relaxed clerk, explains why Portland is a mecca for record shops. “It’s the pace of the town,” he says. “People slow down.”
“Brewvana,” as Portland is sometimes called, is also regarded as the craft-brewing capital of America. Committed to exploring another important aspect of local culture, you head to the east side, home to Breakside, one of the best brewpubs in town. Your fedora-wearing bartender, Jack Johnson, recommends the Salted Caramel Stout and a Kumquat Wit tinged with fruit and a bite of coriander. “Trust me,” Johnson says of the odd-sounding flavors. You do, and are duly rewarded.
From Breakside it’s a short bus ride to your dinner spot, Lincoln Restaurant. The first eatery opened by “Top Chef Masters” alum Jenn Louis, Lincoln offers Pacific Northwest cuisine that emphasizes local ingredients. You start with one of the few exceptions to this rule—the slow-cooked, impossibly tender grilled octopus—followed by baked hen eggs and Forty-Seven Percent Chicken, wryly named, Louis explains, because, served minus the wing, “it’s not a half chicken.” Even a few percent shy, it’s an exceptionally good bit of bird.
It’s late, so you head back toward the Ace. On impulse, you decide on one more detour before bed: Pépé le Moko, a narrow subterranean bar that feels like the dining car of a train going through a tunnel. Your bartender, Talia Gordon, insists you try a Grasshopper. “It’s like an adult milkshake,” she says, passing you a glass of mint green froth. The booze snob in you is skeptical, but you slurp it down and decide that all desserts should taste like this. Later, back in your room, you drift off to Elliott Smith whispering from the turntable: “I’ll show you around this alphabet town.”
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.
DAY THREE | You’ll be doing a bit of driving today. First you zip across the Fremont Bridge and up to Alberta Street, the main drag of the Alberta Arts District, which would be the Brooklyn of Portland if all of Portland weren’t the Brooklyn of Portland. Your destination is Beast. Here, chef Naomi Pomeroy, a 2014 James Beard Award winner, runs a bright, homey one-room space with two large communal tables bracketing a prep station. Clearly, Beast’s reputation has traveled: All but two of the eight people at your table are out-of-towners.
“It’s always been this communal setup,” server Lisa Perry says. “You get to meet people you wouldn’t normally meet.” So it is you share a convivial four-course brunch of a rhubarb clafoutis (custard with whipped cream and bacon); a light hash made with pork shoulder, fresh vegetables and a poached duck egg; a cheese plate; and a thick cube of chocolate cake. It is possibly the best brunch you’ve ever eaten.
Having fueled up, you’re ready to split town. One of Portland’s selling points is its proximity to a host of beautiful natural landmarks. Just a few minutes east of town you find the Historic Columbia River Highway, which winds up a hill to Vista House, a 97-year-old sandstone and marble rotunda perched on a cliff high above the massive Columbia River Gorge. You soak in the view, thinking that it hasn’t changed much since Lewis and Clark rafted through on their way to the Pacific a couple of centuries ago.
From here you descend back into the canyon, the road winding through Douglas firs, over old stone bridges and past waterfalls until you reach 620-foot-high Multnomah Falls, the second-tallest year-round cascade in America. You pull over and walk along Multnomah Creek, looking for spawning salmon, then climb the trail to Benson Bridge. You pause here for a while, enjoying the mist from the powerful falls on your face.
An hour east of Portland you reach Hood River, where you stop for lunch at the Double Mountain Brewery. You order a dry-hopped Vaporizer pale ale and scarf down a brick-oven pizza topped with goat cheese, kalamata olives and peppadew peppers. From here, you wander around the corner to a microbrewing pioneer, the employee-owned Full Sail Brewing Co. You grab a seat on the deck, looking out over the river, and nurse a bourbon barrel–aged porter, watching windsurfers flit about on the water.
Upon returning to the city, you check in at the eighth-floor lobby of the Nines hotel, beneath a seven-story atrium that bathes the luxe (and LEED-certified) interior in sunlight. You drop your bags and munch on the cheese plate in your room, which has a view of Pioneer Courthouse Square, the lively red-brick plaza known as “Portland’s Living Room,” before heading up to the rooftop bar, Departures. The vibe is different up here; with the wall panels glowing pink and purple and the bling-flashing crowd on the sun-blanched rooftop, you feel as if you stepped off an elevator in Vegas.
Back on the ground, with the sun still shining, you stroll across the Burnside Bridge to dinner at Le Pigeon, where you sit before chef Gabriel Rucker’s open kitchen and watch flames rise from the range as the tattooed cooks deftly prepare a succession of adventurous French dishes: suckling pig croquettes, sturgeon pastrami, beef-cheek bourguignon, shrimp-crusted halibut. Each course is delicious and complex and comes with a perfect drink pairing. You do not have room for dessert.
It’s your last night in town and you’re ready to rock out. You’ll be doing this practically next door, at the Doug Fir Lounge. Once a seedy motel, the property was converted a few years ago into a boutique hotel and a bar that looks like a modernist hunting lodge that doubles as one of the city’s best music venues. As Nashville-based indie songwriter Katie Herzig and her band take the stage, you look around the crowd—the studiously casual, comprehensively inked Portlanders who have helped make this the hippest town in America—and decide there may be an even better place to mark the end of your visit, a place that’s conveniently located right up the street.
“People who grow up here or move here love it,” says Gin Hicks, an artist at Fortune Tattoo. “There’s an intense need to preserve it and nurture it and take care of it, and that rolls over into how people express themselves.” With this, she clicks off her tattoo gun, pulling away to admire her work. You say goodnight and head back across the Burnside Bridge, the city lights twinkling on the river, a bright red rose tingling on your forearm.