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A Cool Haven in Portland

The northwestern Oregon city thrives in winter with activities that will keep attendees full of seasonal cheer

By Amanda Christensen

Lan Su Chinese Garden || Photo by Celeste Note

As the cooler months bring in lower temperatures and more rain to the Pacific Northwest—so much rain that it keeps the region lush and green—places like Portland take it by storm. “In the wintertime, Portland’s brand of cozy culture finds a home at the intersection of wonderfully misty winter days and cozy indoor pursuits like coffee shop hopping to sampling craft beers across 70-plus breweries,” says Dione Williams, director of convention sales at Travel Portland. The city has several museums or galleries to entertain attendees with an affection for the arts, alongside notable event venues and arenas that suit large, lively events well.

“The city also has several beloved local events that return every winter season, including Lunar New Year celebrations at Lan Su Chinese Garden and the vibrant Winter Lights Festival,” Williams adds. “January hosts Portland Music Month while February brings with it the annual PDX Jazz Festival, among countless others.” Attendees can also catch the Christmas Ships decked out in Christmas lights sailing down the Willamette River through the month of December.

When hosting events in the City of Roses, ensure your attendees bring their best rain jackets to spend time strolling the streets before convening and networking at any one of Portland’s memorable venues, hotels, or restaurants. “In Portland, our goal is for groups to turn meetings into memories with a winter experience that will leave attendees wanting more for seasons to come,” says Williams.

A Reliable Support System

Portland has venues to bolster events of all kinds and provide the necessities a planner might be looking for. “The flexible meeting spaces found throughout the city are one-of-a-kind, brimming with personality, and adorned with local artisanal touches from makers, designers, and artists,” Williams notes. For a traditional large-scale convention, consider the LEED Platinum-certified Oregon Convention Center (OCC). The venue boasts 470,000 square feet of function space across exhibit areas, meeting rooms, and ballrooms. The Hyatt Regency Portland is situated adjacent to the OCC and offers 600 guest rooms alongside a favorable mix of event spaces. “The Portland Expo Center is Oregon’s largest multipurpose facility,” Williams explains. “The 53-acre campus boasts five spacious exhibit halls, totaling over 333,000 square feet, and 10 varied meeting rooms.”

If planners want something a bit more avant-garde, consider hosting at the Oregon Museum of Science and Industry, which “brings science to life with hundreds of interactive exhibits and displays,” Williams adds. Or, to get attendees up close with Oregon wildlife, gather at the Oregon Zoo located only minutes from the Portland city center. Groups of up to 5,000 can convene for events, social receptions, holiday parties, and more. Side Yard Farms in Portland’s Cully neighborhood turns its greenhouses into cozy dining spaces for smaller, more intimate gatherings and features a catering menu of grown-on-site cuisine and ingredients.

The Benson Portland || Courtesy of The Benson Portland, Curio Collection by Hilton

Hotels That Wow

When it comes to hotels that work well for groups large and small, Williams says the collection in Portland is wide-ranging with more than 10,000 rooms in the heart of the city. Hotel Eastlund is a Forbes Four-Star property located minutes from the OCC and features 168 guest rooms, five meeting rooms, a rooftop deck with panoramic city views, and an executive business center. Opened in October, The Ritz-Carlton, Portland, is the city’s first five-star luxury hotel and is sure to be a hot spot for leisure and business travelers alike. “The hotel [has] exceptional meeting and event spaces evoking the surrounding grandeur of the Pacific Northwest,” says Williams. “There [are] nine event rooms and 16,000 square feet of luxurious meeting space.”

Featuring stunning downtown views and original artwork, The Nines is a LEED Silver-certified property near Pioneer Square and home to 14 creative and contemporary function spaces. If you want to add a touch of Portland history to a gathering, stay and host at The Benson Portland, Curio Collection by Hilton. The property is a Portland landmark that has been operating since 1913. Consider hosting in The Benson’s wood-paneled Regency Boardroom, the Crystal Ballroom, or the expansive Mayfair Ballroom with space for up to 500 attendees. Other properties available for events include The Bidwell Marriott Portland with 3,700 square feet of event space, The Paramount Hotel with 154 guest rooms, and the Portland Marriott Downtown Waterfront hotel with 45,000 square feet of event space and a design that reflects the city’s love of nature.

Dine Like a Northwesterner

“Portland’s culinary scene is an unforgettable mix of global fare and intriguing flavors, incorporating ingredients sourced from purveyors right here in the Pacific Northwest,” says Williams. “The array of culinary experiences you can have here reach far and wide, from rentable restaurants and venues like Hunt & Gather that are perfect for buyouts, to catered experiences from chefs who drive Portland’s inventive culinary pop-up scene.” One of the most iconic parts of Portland’s food scene is its Food Cart Pods, bands of food and beverage trucks dotting the streetscapes across the city. Newly opened options include Midtown Beer Garden and Lil America.

Opt for a James Beard Award-winning experience at Kann, which made The New York Times’ 2022 Restaurant List of best eateries in the country and boasts a delicious Haitian menu using Pacific Northwest ingredients. Kann has the private Yanick Room for groups up to 40. Other restaurants to consider hiring for catering include Jeju Restaurant, Takibi, Dolly Olive, Nostrana, Canard, and Coquine. And for the wine and beer lovers in attendance, sip on a glass (or flight) at Mermosa Winery + Restaurant, Amaterra Winery (which just recently opened a new covered outdoor private event space), Abbey Creek’s downtown tasting room, Grand Fir Brewing, or Assembly Brewing.

Only in Portland

And of course, throwing in some activities for your group to enjoy and bond over is a must for any event, and planners can make it even more special by choosing some that are truly unique to the City of Roses. “Portland is a launch pad for a plethora of indoor and outdoor activities year-round,” says Williams. “Band together in an escape room; craft at Creative Culture, WildCraft Studios, or DIY Bar; [or] get creative in the kitchen during a Cook-shop culinary session.”

Taking eventgoers for a visit to the legendary Powell’s Books is a no-brainer. The landmark covers an entire city block and showcases shelf after shelf of books and magazines, as well as the Guilder Cafe for coffee and small bites. Challenge colleagues to a game of pickleball at the newly opened My People’s Courts or pingpong at Pips & Bounce. Check out Hopscotch for an immersive experience that will bring out the inner child of attendees.

“We don’t let the winter weather dampen our zest for the outdoors [either], so lace up the waterproof boots and hit the trails in Forest Park,” Williams adds. “The juxtaposition between urban and natural areas that exist in Portland simply cannot be duplicated. … Opt for a winter walk through Portland Japanese Garden, Lan Su Chinese Garden, or Pittock Mansion.”

Consider a day-long excursion to the Oregon Coast for beach strolling and whale watching. Amtrak offers bus tickets at a discounted price for groups of 15 or more with roundtrip routes going to waterfront locales like Cannon Beach and Astoria. While you might need to keep an umbrella with you throughout your Portland stay, there is no doubt a liveliness to the city that will bolster unforgettable events and leave attendees with lasting memories.