12 of the Hottest Things to Eat and Drink in Portland this Winter

Portlanders know all about inclement weather. Winter temperatures can drop to the 30s (and the skies can drop more than 10 inches of rain in a single month). They also know their way around and through that weather, and you’ll find hearths and outdoor fire pits, soul-soothing comfort food and cocktails to bring a warm flush to your cheeks all over the city. Chart a course for coziness with these 12 offerings (and destinations).

For a pitch-perfect cocktail, look no further than Café Nell — a sparkling neighborhood bistro in the Alphabet district — and wintry offerings like bartender Michael Dreher’s It’s an Old-Fashioned Life, inspired by "a fireplace always lit and the smell of rosemary and cinnamon simmering on the stovetop.” Can’t make it to PDX? Channel Dreher’s genius by creating his seasonal simple syrup (one cup each of water and honey, boiled together in a sauce pan and combined with a sprig of fresh rosemary, a cinnamon stick and two fresh cloves, then cooled, strained and refrigerated), spooning 1-1/4 ounces of the mixture into an old fashioned glass, adding one extra-large ice cube and finishing with two ounces of Jim Beam. Stir, then garnish with a flamed rosemary spring and sliced cranberries.

Eleven years ago, Liberty Glass sprouted from a two-story pink house at the bottom of a hill in the Mississippi Avenue district. Siblings Rose and Jason McCormick named their bar and restaurant after their great-grandparents’ post-Prohibition establishment in Ohio, and the funky family vibe they’ve cultivated is readily apparent. The quirky space still sports residential details like an upstairs bathtub, and the food they serve is an elevated homage to the after-school snacks your mom might make. Tuck into their hefty grilled cheese sandwich (a fat stack of mozzarella, two kinds of cheddar and chives on slabs of buttered bread) with a side of spicy tomato soup, and make yourself at home.

Continue your tour of former-Mississippi-Avenue-homes-turned-bars at the 1920s bungalow that’s now The Rambler, a neighborhood destination with a generous array of fire pits in both its front and backyard spaces, a towering pile of board games and steaming hot drinks like Spanish Coffee. This winter warmer is almost as fun to prep as it is to sip: The Rambler’s bartenders pour Cruzan 151 rum into a mug, set it aflame, add a few dashes of a cinnamon-and-nutmeg blend (hence those spectacular sparks, above), then add their house mixture of triple sec, Kahlua and Appleton Estate rum. Topped with coffee, whipped cream and a few more dashes of spice, it’s the boozy equivalent of your favorite sweater.

Downtown Portland’s historic Heathman Hotel had a reputation for its English tea service when James Beard Award winner Vitaly Paley opened Headwaters, its restaurant featuring local produce and seafood, in 2016. He decided to celebrate family traditions from his childhood in the Soviet Union by putting a Russian spin on the afternoon tea ritual, and the result — a kaleidoscopic, prix-fixe presentation of sweet and savory eastern delicacies — is now a Sunday mainstay (and a daily treat during the holidays). Reserve a seat beneath the stately crystal chandelier in the Heathman’s two-story Tea Court and surround yourself with bites like mushroom-stuffed piroshki, Ukrainian poppy-seed rolls, Georgian cheese bread and sour cream and walnut cake like Paley’s grandmother used to make.

A collaboration between Trailhead Coffee Roasters and Ranger Chocolate Company, Portland’s first coffee and chocolate tasting room offers a 3 1/2 hour walking tour of the East Side chocolate scene on Saturdays. Want to cut to the chase? Head straight to Cup & Bar for ethically-sourced, small-batch coffee and artisanal chocolate and treats like Campfire Toast, featuring crusty sourdough bread from Grand Central Bakery, a hazelnut-chocolate spread made in-house (sorry, Nutella), toasted hazelnut, all-natural vegan marshmallows and chocolate chunks.

Settling on a favorite among Blue Star Donuts’ seasonal offerings is no mean feat; their Charred Date Custard, Peppermint Hot Chocolate and Smoked Eggnog Brûlée are all showstoppers. That said, we’re partial to the sufganiyot, a fried jelly donut that’s one of the most popular Hanukkah foods in Israel (and served to commemorate the holiday around the world). The Blue Star version is made with pillowy 18-hour brioche dough, filled with a blend of Oregon Growers apricot preserves, hand-harvested flake sea salt from Jacobsen Salt Co., vanilla and cardamom, then tossed in powdered sugar.

Modern Times takes its name from a utopian community built on Long Island in 1850. In the 21st century, it’s a bunch of beer, coffee and vegan cuisine experts offering their own take on “what a more perfect society might look like.” That translates to California and Oregon breweries, restaurants, cafes and tasting rooms that offer everything from craft beers and lovingly-roasted coffee to — at their massive Belmont Fermentorium — hearty, spicy batches of goodness like their Tom Kha, a coconut-lemongrass broth spiked with maitake mushrooms, tomato, herbs and chili oil. More in the mood for a burger with your beer? The local alternative paper Willamette Weekly named Modern Times’s Double Burger the best vegan version in the city. Pro tip: During the day, the rooftop Sky Lounge serves up city views along with brews.

Let’s talk perfectionism: The team at Kayo’s Ramen Bar refers to their key ingredient as “Noodle 47” because they hit upon its ideal texture, taste, color and “slurp” after 46 unsatisfactory tries (and three months of experimentation). They now dish up those noodles with Assari-style bone and vegan broths and 17 sauces, all made fresh daily. One star of the menu is their delicate wintery Snow Ramen, featuring ginger, citrus and chilies, topped with lemon, shiitake mushrooms and grated daikon “snow,” and served with chashu pork or tofu. Pair it with Taisetsu Junmai Ginjo, a sake that’s slow-aged in igloos in Hokkaido and has a floral aroma with a hint of licorice and pepper. If/when you fall in love with Kayo’s famous array of Umami Salts, take a bottle home for $6.

Winter patios with fire pits are a thing in Portland, and it’s hard to beat the partially-covered, fully-heat-lamped outdoor space at The Richmond Bar, where thoughtful cocktails rub shoulders with fortifying pub fare (and the late-night menu is served until 2 a.m.). Draw inspiration from the heavily-supplied wagon trains that hit the Oregon Trail in the 19th century and order up a few of the Richmond’s ever-changing, always-satisfying hand pies (meat and veggie offerings rotate seasonally) to warm your pockets en route to your next adventure. A responsible traveler should always be well-provisioned, no?

The first-generation daughter of Soviet Jewish immigrants who settled in Chicago, chef Bonnie Morales is the culinary soul of what some critics have called the best Russian restaurant in America. Since 2014, Kachka has paid tribute to her family’s cuisine with the same zakuski (appetizers, or “something to bite after”) they used to welcome newly-arrived relatives. Those dishes — and the nips of vodka that should come before and after them and the mains that come after them — are all excellent ways to fill yourself on a winter evening. Whatever you choose, conclude your feast with Morales’s mouth-watering poached quince, paired with black tea and fresh thyme, old-school Russian ice cream — known as plombir — a sushki (a sweet Russian bread ring) crumble and a dusting of poppyseeds.

“This is definitely the season of comfort and we strive to bring that every day,” says Wendy Hessel, owner of Fireside (an intimate neighborhood gastropub in northwest Portland with, count ‘em, two fireplaces). But don’t just take her word for it. Fact-check that claim in delicious fashion with an order of the potato rosti, Swiss potato hash browns topped with chanterelles, a sous-vide egg, mizuna, shallot, bread crumbs. and chimichurri. Want a seasonal cocktail pairing? Try the Harvester’s Stone Fence (rye whiskey, pumpkin apple cider, lemon and spices). “We also have an amazing ginger turmeric toddy we feature in the winter months,” Hessel adds. Challenge accepted.