How To Plan The Perfect Winter Weekend In Portland, Oregon

With temperatures hovering around freezing and glimpses of daylight few and far between, it’s easy for our spirits to also sink this time of year. So why not do as Portlanders do? Instead of bemoaning the cold and dark, they’ve learned to adapt to mother nature and makes the best of all four seasons.

Because while winter might not be the most pleasant or picturesque, per se, it does have its own unique perks. You have easier access to all of The City of Rose’s terrific restaurants, bars, and cultural attractions; hotel rates are lower and far more competitive; and the city will feel like your own without the usual tourists.

So ahead, how to plan an unforgettable winter weekend in Portland.

Where to Stay

No Portland hotel channels hygge, the Danish term describing a feeling of cozy comfort and contentment, better than Kimpton RiverPlace Hotel. The 84 guest rooms and suites sport an earthy palette, and plenty of nature-inspired touches (think botanical art, branch side tables, canoe paddles) to usher the outdoors in. If the snowy and rainy weather is weighing you down, just peer out your window to see Willamette River front and center—it’ll immediately soothe your soul. And under Executive Chef Alexander Diestra, the all-day restaurant King Tide Fish and Shell forgoes the bland continental food of most hotels and instead turns out dishes taking inspiration from all over the world, from Japanese curry empanadas to Kanpachi crudo finished with blood orange and chili vinaigrette.

Seeking a stay that captures the wonderfully quirky and inclusive spirit Portland is famous for? Look no further than Next at Jupiter. With a prime address on East Burnside—just steps from some of the best restaurants and bars like Canard, Kann, and Nong’s Khao Man Gai—the 67 rooms of this boutique property may skew snug, but make use of the space in smart ways. The shower, for example, is partitioned off with glass instead of a wall, and replacing a bulky desk is a long, slim bench-like table perfect for work and stowing your belongings. Even the headboards, striking black-and-white photomontages by local artst Beth Kerschen, were thoughtfully considered. For unbeatable views of the urban landscape and mountains, book a Next Level X Room on the top floor.

Where to Eat and Drink

Situated in the Pearl, Janken is the sophisticated restaurant Portland so deserved after the last few years. Executive Chef Rodrigo Ochoa—who was at Miami hot spots StripSteak by Michael Mina and Komodo—assembled a world-class team (including Korean executive sous chef Juah Oh) for the menu that leans heavy on Japanese and Korean flourishes. While the traditional nigiri and sashimi is absolutely pristine—our server said the fish is flown in three times weekly—it’s Janken’s original creations that really shine. Begin with the Hamachi Crispy Rice finished with peppery-citrusy yuzu kosho and end with the house bingsu, an over-the-top riff on the humble Korean shaved ice treat smothered with berry sauce, cheesecake chunks, and graham cracker crumbs.

A passion project in ways more than one, Grand Fir Brewing is the long-awaited brewpub by the beloved husband-wife duo of Whitney Burnside and Doug Adams. As Portland’s first female brewmaster, Burnside develops the regularly rotating beers, ranging from the sprucey Old Growth Pale Ale to the very sippable Tack Shack East Texas Lager, an homage to her Texas born-and-bred husband. For the food, celebrated chef Adams of Top Chef fame put together a consise menu of hearty bites for all appetites, like crispy potatoes dripping with raclette beer cheese and the house Grand Fir Burger. The description may come across as fairly basic (two grass fed beef patties, sauce, American cheese, the usual veggies), but it’s hauntingly satisfying and yields a sum far more enjoyable than its individual parts. Could this be Portland’s best burger?

Locals and out-of-towners are still clamoring for reservations at hot spot Kann by Gregory Gourdet, and for good reason, so here’s a tip: you can have just as much fun pairing fruity cocktails like the Falernum-laced Jean-Michel and imaginative zero-proof drinks with Caribbean snacks—the doubles and chicken wings are especially craveable—at his sleek subterranean lounge Sousòl. It’s dark, a bit rambunctious, and the quintessential antidote to fend off the winter blues.

Discreetly tucked away in South Waterfront, Lilia Comedor is where Mexican-American chef Juan Gomez sends out bold, colorful, and hyper-seasonal plates that are as pleasing to the eyes as they are to the palate. Though you can order botanas (snacks), platos fuertes (main courses), and postres (desserts), Gomez is not bound by traditional definitions and categories. Just do yourself a favor and go, and let yourself fall under Gomez’s culinary spell.

Run by a group of whipsmart and talented women including chef Diane Lam and wine director Wei-En Tan, Alphabet City’s Alouette is a lovely neighborhood nook serving up Viet-French cuisine such a mussels steamed in a deeply savory and subtly spicy lemongrass-tomato broth—all on charming vintage china, to boot. The wine list is equally notable, with a strong showing of female producers and natural bottles.

What to Do

Portland Art Museum might hold the title as the West Coast’s oldest museum—it was founded in 1892—but the progressive programming squarely focuses on what’s relevant now. Case in point? The current exhibit, Dakota Modern: The Art of Oscar Howe, is a remakrable and stirring survey by the acclaimed Yankton Sioux painter known for depicting Native American traditions with a modern lens blissfully free of Western stereotypes and tropes.

Long before the Pearl became the city’s toniest neighborhood, Amy Adams set up Adams and Ollman back in 2013. Unlike fellow gallerists who are more preoccupied with cruising the fair and gala circuit to keep their names relevant, Adams actively seeks out self-taught creatives and other artists typically neglected by the gatekeepers of the contemporary art world. Stephanie Chefas Projects specializes in provocative, challenging work by emerging artists, while Augen Gallery has been setting the standard for limited-edition prints by art titans like Roy Lichtenstein, David Hockney, and Andy Warhol.