Why You Should Plan a Trip to Portland, Oregon This Winter

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While summer is peak tourist season in Portland – which can withstand those wonderfully warm but not comfortably dry, hot temperatures – here’s a tip: winter is also a great time to visit. Of course, the weather may be marked by overcast skies and drizzle, but there is still many to live and enjoy. (Plus, hotel rates at this time of year are incredibly affordable.) So ditch your umbrella, don a raincoat like the locals do — those at Rains are particularly stylish — and follow these recommendations to get the most out of it. a winter holiday in the always charming town of Roses.

Where to stay in Portland

Prefer to hang out on the Eastside of the city? Then book a room at the Grand Stark Hotel. Occupying a historic 1908 structure that once housed a hotel and furniture warehouse, the 57-room boutique property feels quintessential Portland. Rooms nod to the Pacific Northwest with original wood floors and spruce green accents, while the Grand Stark Deli is a cheerful nook for coffee and simple bites. But it’s the newly opened Bar Chamberlain that’s a real gem and the city’s best kept secret – but hopefully not for long. Hidden away from the main lobby, it’s everything a hotel bar should be: cozy and welcoming with quirky craft cocktails and equally tantalizing cuisine. (The chicken, which is sous vide, roasted and accompanied by crispy fries, is a winner.)

If you want a comfortable stay all over town, but don’t need too many bells and whistles, Dossier Hotel is for you. Part of Provenance Hotels, the classic 205-room property may not dazzle in terms of design, but other touches (like friendly staff and free morning coffee and pastries) help it shine. On top of that: the accommodations are quiet – a must if you’re staying in a bustling city center – and well-appointed for a good night’s rest. If you book a room on the 14th floor, you will also be rewarded with an impressive view of the city.

Where to eat in Portland

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

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

Despite opening in 1944, RingSide Steakhouse remains a staple in town. The dining room is beautiful (imagine dim lighting and red leather banquettes), the chops are grilled to perfection – RingSide is one of only two restaurants in the area serving A5 Kagoshima Wagyu – and the service is polished, but the best seat in the house is at the bar. This is where you can enjoy frozen martinis and the legendary onion rings, while people-watching.

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

Short on time ? You’re in luck, because there are plenty of great 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 center inspired by Florence’s Mercato Centrale. So whether you’re craving ready-made Italian bites (romaine pizza, salads, pasta) or want quality ingredients (including lesser-known and affordable wines) for a meal at home, you’ll find everything you need. you need under one stylish roof.

In the Alphabet district, Burma Joy specializes in homemade Chinese-Burmese dishes like green tea leaf salad, a bowl of raw vegetables, crunchy nuts and seeds, and earthy Laphet (leaf dressing fermented tea). Located downtown, Lil’ Shalom offers casual Mediterranean dishes such as hummus with pita, chicken baharat kebab and falafel sandwiches in a cozy and comfortable setting. And while there’s no shortage of bargains in Portland, MidCity SmashBurger food truck stands out with its simply sublime burgers made with smashed beef patties, American cheese and signature sauce for the sweet price of $5.

What to do in Portland

Blink and you’ll miss Adams and Ollman, the small but mighty gallery launched by Amy Adams in 2013. By showing the works of 20th-century creators who are mostly self-taught or have no conventional training, Adams pushes the boundaries of what that people think of as contemporary art. Now through March 19, guests can check out Conny Purtillit’s the groundan ongoing multidisciplinary collaborative project by the Los Angeles-based artist and various participants, including Edgar Arceneaux, Taylor Davis, and Luc Fuller.

Established in 1892, the Portland Museum of Art may be the oldest museum on the West Coast, but in its true Portland form, it keeps things extremely relevant with inclusive and progressive programming – as evidenced by Mesh, a showcase of four contemporary Indigenous artists addressing social issues and advocating for change. And on February 19: Frida Kahlo, Diego Rivera and Mexican modernism, will be revealed to the public.

The meticulously maintained Japanese Garden in Portland opened in 1967 to symbolize peace between Japan and the United States after World War II. And in 2017: it unveiled a massive expansion called the Cultural Crossing Expansion, which includes three new garden spaces, a castle wall by Japanese stonemason Suminori Awata, and the culture village by revered architect Kengo Kuma.

Event Cosmetics is a go-to place for bridal and special occasion makeup, but owner and industry veteran Katherine Sealy also offers some of the best facials in town, thanks to Geneo. The innovative and non-invasive dermatological treatment offers personalized and targeted results by combining three technologies: Oxygeneo, RF and Ultrasound. So in less than an hour, your complexion – no matter if you’re acne-prone, sensitive or dry – will not only look healthy right away, but for weeks to come.

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