Portland may be just the 28th most populous city in the U.S., but it punches well above its weight class as a foodie destination. This is a city of trendsetting, abundant food trucks, the concepts of local and organic taken to the max, and way more notable places to eat than there are meals in the day. Don’t let that deter you, though—you can take a good bite of the scene in one weekend.
You’ll probably roll into town well after dinnertime, but get your trip started right with a nightcap. In the Pearl District, the Teardrop Cocktail Lounge’s craft mixers—such as specialty liqueurs, syrups, digestifs and vermouths—are made by hand. If you’re wondering about any unfamiliar words on the menu, turn to the handy glossary for clarification. Another good nightcap option is the intimate, leather-bedecked Multnomah Whiskey Library, where there’s often a wait for non-members (yes, just like a real library, there are memberships here). Once you get in, though, you’re sure to be wowed by the wall of spirits and the tableside service—bartenders roll over a cart and create your concoction right in front of you.
For breakfast, start with a classic: Mother’s Bistro & Bar. The dining rooms here feature gilded mirrors, crystal chandeliers, and gold accents throughout, making this an elegant yet cozy stop. Get a taste of the South with the Biscuit Breakfast, with homemade buttermilk biscuits topped with country sausage gravy; embrace the Northwest with the Wild Salmon Hash, served with leeks, potatoes and a touch of cream; or satisfy your sweet tooth with the Crunchy French Toast, dipped in cornflakes and grilled golden brown.
Give yourself a little time to digest because in the afternoon, it’s worth heading out with Forktown Food Tours on their North Mississippi Avenue tour. This artsy neighborhood on Portland’s north side is home to some tasty establishments you might miss if you only hang out downtown. Learn about the history of the area while noshing on crostini with local farmstead cheeses, Korean-Mexican fusion bulgogi pork tacos, truffle fries, lemon cookie and lavender honey ice cream sandwiches, and much more. The bites are small, but don’t worry about going hungry—you will be full by the end.
You’ll be done just in time to hit up happy hour. A fun one is at Bacchus Bar inside the lobby of Hotel Vintage. The recently renovated hotel sports a laid-back, retro-modern vibe, with plenty of seating and sipping options. Order a Willamette Valley Pinot Noir and some sea salt pistachios, then head up to the second floor, where an old-school game room features gems like Atari and shuffleboard.
Choosing a dinner spot is next to impossible given all the choices, but if you’re looking for a high-end, multi-course meal that’s a true experience, Castagna is the place. The modernist restaurant is in the vein of molecular gastronomy meets Pacific Northwest foraging, with each course a work of art. Order the tasting menu from Chef Justin Woodward and be prepared to sit back and savor.
If a late-night hunger pang strikes, embrace the idea of high/low eating and find something on the opposite end of the spectrum from Castagna: the famed Voodoo Doughnut. There’s always a line at the 24-hour original location, but if you go in the wee hours, you’re less likely to have to wait long—plus, you can commune with the other crazy people eating donuts covered in cereal, topped with Tang, and in the shape of voodoo dolls in the middle of the night.
In the morning, follow the crowds to Tasty n Sons, an industrial-chic restaurant serving small and large plates of new American cuisine. The Chocolate Potato Doughnut and Maple Bacon Wrapped Dates are favorites from the small plates; for something heartier, order the Burmese Red Pork Stew. Pair your food with the Tasty Mary, a classic Bloody Mary, or go with one of the other four Mary variations (there are tequila, aquavit, gin and vodka options).
On your way out of town, there’s time for one last treat. No matter how much ice cream you’ve eaten in your day, there’s bound to be a flavor combination new to you at Salt & Straw, which began as a food cart and has now expanded to three brick-and-mortar locations. Pear & Blue Cheese, Stumptown Coffee & Burnside Bourbon and Almond Brittle with Salted Ganache are just a few of the tempting varieties to send you home satisfied.
If You Go
422 SW Broadway
1752 SE Hawthorne Boulevard
Forktown Food Tours
Starts at Mee Sen Thai Eatery
3924 N Mississippi Avenue
Mother’s Bistro & Bar
212 SW Stark Street
Multnomah Whiskey Library
1124 SW Alder Street
Salt & Straw
2035 NE Alberta Street
Tasty n Sons
3808 N Williams Avenue
Teardrop Cocktail Lounge
1015 NW Everett Street
22 SW Third Avenue