Why You Should Plan A Trip To Portland, Oregon, This Winter

While summer is peak tourist season in Portland – who can resist those wonderfully warm-but-not-hot and comfortably dry temperatures – here’s a tip: winter is also a terrific time to visit. Sure, the weather might be marked by overcast skies and drizzly rain, but there’s still plenty to experience and enjoy. (Plus, hotel rates this time of year are incredibly affordable.) So ditch your umbrella, throw on a slicker like the locals do – the ones from Rains are especially stylish – and follow these recommendations on how to make the most of a winter vacation to the ever-charming City of Roses.

Where to Stay in Portland

Prefer to hang in the city’s Eastside? Then book at room at Hotel Grand Stark. Occupying a storied 1908 structure that once was home to a hotel and furniture warehouse, the 57-room boutique property feels quintessentially Portland. The rooms nod to the Pacific Northwest with original wood floors and pops of spruce green, while Grand Stark Deli is a cheery nook for coffee and simple bites. But it’s the just-opened Bar Chamberlain that’s a real gem, and the city’s best kept secret – but hopefully, not for long. Hidden away off the main lobby, it’s everything a hotel bar should be: cozy and welcoming with original craft cocktails and equally enticing food. (The chicken, which is sous vide, roasted, and paired with crispy shoestring fries, is a winner.)

If you want a comfortable stay across town but don’t need excessive bells and whistles, Dossier Hotel has you covered. Part of Provenance Hotels, the classic property with 205 rooms might not dazzle in terms of design, but other touches (like the friendly staff and complimentary morning coffee and pastries) help it shine. On top of that: the accommodations are quiet – a must if you’re staying in bustling downtown – and well-appointed for a good night’s rest. If you book a room on the 14th floor, you’ll also be rewarded with impressive city views.

Where to Eat in Portland

In the space that once housed Portland institution Ned Ludd, Cafe Olli bridges the old and new by coupling the original wood-fired oven and affinity of simple, seasonal ingredients with an Italian-leaning menu of rustic breads, pizza, and produce-driven plates. You’ll feel even better dining at this buzzy newcomer knowing it’s employee-owned, and feeds those in need with a community meal offering.

Though Carlo Lamagna was named a Food & Wine Best New Chef 2021, he’s been a fixture of Portland’s culinary scene for years. And at his first solo venture Magna Kusina, which opened in August 2019, Lamagna honors his Filipino heritage with his takes on crowd-pleasing Lumpia, Sisig, and Biko in a lively space featuring an open kitchen. Eating here doesn’t feel like a restaurant, but a boisterous house party where Lamagna belts tunes and downs lumpia-garnished shots, and everyone is welcome.

Despite opening in 1944, RingSide Steakhouse remains a beloved city fixture. The dining room is handsome (imagine low lighting and red leather banquettes), the chops are grilled to perfection – RingSide is one of only two area restaurants serving A5 Kagoshima Wagyu – and the service is polished, but the best seat in the house is at the bar. It’s where you can throw back ice-cold martinis and the legendary onion rings, while engaging in some gripping people-watching.

Not feeling another grey day in Portland? Then swing by Hey Love. Co-owned by local industry veterans who champion good vibes for employees and guests, this buzzy lounge whisks you to an island paradise with its tropical foliage, friendly staff that feel like family, and unabashedly fun cocktails (including slushees and shots). If you’re peckish, try the nachos (called Nacho, Nacho Man) heaped with queso, pork chile verde, pickled jalapenos, and housemade hot sauce.

Short on time? You’re in luck, as there’s plenty of terrific options in town. Co-owned by Sarah Schafer and Anna Caporael (formerly of Irving Street Kitchen), Cooperativa is a light-flooded, 5,000-square-foot food hall and community hub inspired by Florence's Mercato Centrale. So whether you’re craving prepared Italian bites (Roman-style pizza, salads, pastas) or want quality ingredients (including lesser-known, affordable wines) for a meal at home, you’ll find everything you need under one stylish roof.

In the Alphabet District, Burma Joy specializes in homestyle Chinese-Burmese dishes like Green Tea Leaf Salad, a deeply craveable bowl of raw vegetables, crunchy nuts and seeds, and earthy Laphet (fermented tea leaf dressing). Located downtown, Lil' Shalom turns out casual Mediterranean staples such as hummus with pita, baharat chicken kebab, and falafel sandwiches in snug, cozy setting. And even though bargain eats abound in Portland, food truck MidCity SmashBurger stands out with its simply sublime burgers made with smashed beef patties, American cheese, and signature sauce gently priced at $5.

What to Do in Portland

Blink and you’ll miss this Adams and Ollman, the tiny but mighty gallery started by Amy Adams in 2013. By showing the works of 20th-century creatives who are primarily self-taught or don’t have conventional training, Adams pushes the boundaries of what people consider contempoary art. Today through March 19, guests can check out Conny Purtill’s The Ground, an ongoing, multi-disciplinary collaborative project by the Los Angeles-based artist and various participants including Edgar Arceneaux, Taylor Davis, and Luc Fuller.

Established in 1892, Portland Art Museum might be the West Coast’s oldest museum but in true Portland form, keeps things acutely relevant with inclusive, progressive programming – as evidenced by Mesh, a showcase of four contemporary Native artists addressing social issues and advocating change. And on February 19: Frida Kahlo, Diego Rivera, and Mexican Modernism, will be unveiled to the public.

The meticulously maintained Portland Japanese Garden opened in 1967 to symbolize peace between Japan and the U.S. after World War II. And in 2017: it unveiled an extensive expansion called the Cultural Crossing Expansion, which encompasses three new garden spaces, a castle wall by Japanese stone mason Suminori Awata, and the Cultural Village by revered architect Kengo Kuma.

Event Cosmetics is a top spot for bridal and special occasion makeup, but owner and industry veteran Katherine Sealy also offers one of the best facials in town, thanks to Geneo. The innovative and non-invasive dermatological treatment offers personalized, targed results by combining three technologies: Oxygeneo, Neo-Massage, and Ultrasound. So in under an hour, your complexion – no matter if you’re acneic, sensitive, or dry – will not just look healthy right away, but for weeks to come.