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Jetsetter Guides

72 Hours in Portland, Oregon

Portland’s unofficial slogan? “Where young people go to retire.” And you’ll understand why when you taste your way through its breweries, food trucks, and tasting menus; tool around town on its bike paths and shop your way through its design boutiques. New Yorker-turned-Portlander Marnie Hanel takes us around town.

FRIDAY

You could never be hungry enough to eat every delicious thing this food town has to offer, but while you’re here, it’s your solemn duty to try. Splash out and stay at The Nines, sleep in, then stroll over to Tasty N Alder for a meandering breakfast of shared plates before checking out the perfectly-curated design shops Canoe and Alder & Co. Go ahead and splurge: Oregon shopping is tax-free. Continue on to Union Way, an arcade of stylish stores, to pick up treats proudly made in Oregon: baked goods from Little T Bakery (pack them for an afternoon snack), gumdrops from modern candy shoppe Quin (save them for the movies), and boots from Danner (ship them; they’re heavy.) Set aside an hour, at least, to explore Powell’s, the nationally-renowned independent bookstore, packed to the gills with literary wonders, including two self-published, insider guides that will certainly boost your trip: Hop in the Saddle: A Guide to Portland’s Craft Beer Scene by Bike and Portland’s 100 Best Places to Stuff Your Faces. Buy both.

Meet for a light lunch at chef Kristen Murray’s Maurice, a teensy portal straight to Europe with food so delicately presented, the chef sometimes has to remind iPhone-wielding patrons to eat. (Whatever you do, don’t skip dessert; Murray is rightfully famous for her Black Pepper Cheesecake.) Or, wander through the food truck mecca at 10th and Alder to taste test some of Portland’s best street bites, like the signature chicken and rice at Nong’s Khao Man Gai, or the milk & honey waffle at Gaufre Gourmet.

If the weather is nice, hop the Washington Park Tri-Met Bus #63 to Washington Park and hike up to the International Rose Test Garden, where thousands of roses bloom from April to October. (June is the peak month.) Delight in the plaques bearing the flowers’ creative names. Next, visit the Portland Japanese Garden, a tranquil 5.5-acre sanctuary with a stunning view of Mount Hood.

Descend back into the city, refresh at the hotel, and then hail a cab across the river to Division, the city’s fastest-rising eating street, anchored by chef Andy Ricker’s famed Thai restaurant Pok Pok. Start at urban winery Southeast Wine Collective for a tasting flight of limited production wines. Then head around the corner to Stumptown Coffee founder Duane Sorenson’s stunning Italian spot Ava Gene’s, where chef Joshua McFadden’s dreamy burrata/focaccia number and inventive vegetable sides will wow you even before you get to the pasta. (Make a reservation in advance.) After dinner, if you can possibly fit one more thing in your stomach, head to Salt & Straw for one of the best ice cream cones in America. (To skip the line, cut to the front and buy a pint. We recommend the Sea Salt with Caramel.) Have a nightcap at neighborhood hang Richmond Bar and turn in.

SATURDAY

Wake up and head straight to the Farmers’ Market at Portland State University before the crowd gets too crazy. (It’s open 8:30 a.m. to 2:00 p.m. March-October; 9:00 a.m. to 2:00 p.m. November-February.) Shop the more than 250 vendors for the makings of a picnic breakfast to enjoy on the lawn.

If it’s sunny, rent bicycles (your hotel will hook you up) and pedal over to the Eastside for a self-guided tour of the craft beer scene using Hop in the Saddle, that fantastic self-published book you grabbed at Powell’s. (The routes in the book are organized by neighborhood; you’re in Southeast.) Or, if you’re up for a pretty ride, but not a beer tour, cycle down the Eastbank Esplanade to the Springwater Corridor.

In case of rain, ditch the wheels and walk to the Living Room Theater, an art house cinema with a bar, to see a movie. Then dive into teensy speakeasy Pepe le Moko for oysters and booze from the king of PDX cocktails, Jeffrey Morgenthaler, before cozying up to the fireplace at the swanky Multnomah Whiskey Library.

Make it back to Departure, the rooftop restaurant at The Nines helmed by Top Chef‘s Gregory Gourdet, to catch the sunset and the best view of the city. Relax in your room for a bit before hailing a cab for dinner. Tonight, you’re throwing out the menu and letting chefs Will Preisch and Joel Stocks of Holdfast Dining make all the decisions. Their underground supper club is the most quintessentially PDX dining experience of the moment; as you toast your companions at your communal table, you will congratulate yourself on getting it right. (Book ahead. If you can’t get in, or want to order your own dinner, try the cheerful, delicious Olympia Provisions SE.)

After dinner, walk over to the Doug Fir to see a band, grab drinks by the outdoor fire pits, and enjoy the scene, which looks like an indie film and feels like a great party at another high school—i.e. you’ll fit right in even though you don’t know anyone. Grab late-night French fries at the adjoining diner and head home.

SUNDAY

One of the best things about Portland is how easy it is to skip town, so, for this day only, rent a car. Pick up your wheels downtown, make a pit stop at Levant for the incredible $20 chef’s choice brunch, which spans from shakshuka to glazed pistachio spiced rolls, then head out on I-84 towards the Columbia River Gorge. Take a detour onto the Historic Columbia River Highway to the Vista House scenic lookout. Then, cruise over mossy stone bridges to the famous (read: touristy) Multnomah Falls, Oregon’s tallest waterfall, before driving to the Eagle Creek Trailhead for a hike to Punchbowl Falls. This four-mile trek into an old-growth rainforest isn’t difficult (although there is a daring bit where the trail narrows and the drop-off is steep) and it ends triumphantly, at a waterfall.

Afterward, drive into Hood River for a pint from Pfriem Family Brewers. Walk along the waterfront to check out the windsurfers. Continue your pub crawl with a stop at craft brewers Double Mountain or Full Sail, or, if you’re traveling during the summer or early fall, drive to Hood River U-Pick Organic to pick your own cherries or honeycrisp apples, and to Cascade Alpacas for a furry photo-op.

Then make your way to the airport, to return your rental car and check into your flight, leaving just enough time to hit the pre-security food cart pod and eat Pok Pok Wing’s signature dish before boarding your flight. As if we’d let you go home hungry.