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Portland White Stag sign over Burnside Bridge

Wintertime in Portland

Rain or shine, visit Portland this winter

While most are buckling down for the winter, Portlanders are just ramping up. Portland in the winter means cozy afternoons at your neighborhood bookstore or coffee shop while listening to the sound of raindrops pitter pattering outside. It means hikes at Forest Park where you can get poured on at any moment, but somehow seem to time it perfectly before the rain begins. It means trips to Mount Hood where you can ski all day at three major ski areas and easily make it back to Portland for happy hour prices at local breweries. Winter in Portland also means more restaurant availability to enjoy the root vegetables of the season at the best spots in town.

A few of our favorite rainy-day activities include…

Restaurants with seasonal menus:

  • The menu at Quaintrelle, a cozy restaurant with exquisite food perfect for any occasion, changes seasonally with locally sourced ingredients. Chef Ryley Eckersley takes all the best offerings of each season and turns them into beautiful plates, expertly paired with one of the delicious cocktails on their seasonally-inspired cocktail menu.
  • Located behind Someday PDX, Ruthie’s food cart serves a seasonal menu that draws upon recipes from co-owner Collin Mohr’s grandmother, Ruthie, and locally sourced ingredients. You’ll find pickles, jams and preserves throughout the menu, using pickling and canning techniques inspired by his grandmother.
  • The menu at newly opened Wild North is built around sustainability and full flavor profiles. All of the ingredients are incorporated fully into the menu so nothing goes to waste. With dishes cooked exclusively on a wood-fired grill, the menu changes seasonally to showcase new offerings based on what's fresh and local at the moment.

Cozy up in a bookstore:

  • Opened June 2021, black-owned Third Eye Books is the number one supplier of African Centered books, accessories and gifts in the Portland Metro Area. Owners Michelle Lewis and Charles Hannah have curated a wide selection of thought-provoking best sellers and lesser-known books, working to raise awareness for African-centered books and antiracist literature in the community.
  • A visit to Portland is complete without a trip to Powell’s Books, the world’s largest independent bookstore that just so happens to be celebrating its 50th anniversary in 2021. Its flagship store in Portland’s Pearl District takes up an entire city block, offering 68,000 square feet of used, new, rare, and out-of-print books. To celebrate this milestone, Powell’s Books released its 50 Books for 50 Years. The collection is a self-reflective curation reminding all “to act as a mirror and a beacon.” The perpetual book recommendations at Powell’s Books, though, comes from the beloved “staff picks” cards seen throughout the aisles—each card is like a personal note from a Portlander. Welcome to our city and the books that we read here.

Breweries + urban tasting rooms:

  • Located within The Shops at 10Y, Oregon’s first black winemaker Bertony Faustin took the opportunity to build outside of traditional wine country with the July 2020 opening of Crick PDX. Serving Abbey Creek wine from Faustin’s White Plains winery, a visit to this hip-hop themed tasting room is sure to brighten any winter Portland day.
  • George Johnson, founder, head brewer and pizza chef built Assembly Brewing on a neighborhood craft-brewery dream that caters to patrons 21 and older. Backed by his Detroit roots, proprietary dough recipe, and approachable craft beer, Johnson, the first African American to own and operate a brewery in Oregon, welcomes visitors in the up-and-coming Foster-Powell neighborhood.
  • Opened July 2021, Steeplejack Brewing is perhaps one of the most stunning breweries having opened in Portland over the past year, taking occupancy of a stunning 110-year-old church known for its ornate steeple, long history and incredible stained glass. Patrons enjoy a bountiful menu of ale and lagers complimented by elevated pub food while dining on traditional church pews.

Outdoor activities – rain or shine:

  • With 70 miles of trails, aptly named Forest Park is a popular escape for runners, equestrians and hikers. Located in the city’s northwest corner, this 8-mile-long conservancy is one of the largest urban parks in the nation and offers a respite from urban life for locals and visitors alike. Check out the popular Macleay Park and Wildwood trails, both winding their way around the famed Pittock Mansion.
  • Mount Hood lies in the footprint of the Rose City, offering a bountiful winter playground just 90 minutes to downtown. For skiing and snowboarding, Mount Hood Meadows, Mt. Hood Skibowl and Timberline are great options. Cross-country and snowshoe trails zigzag the mountain, letting outdoor enthusiasts reconnect with nature while traversing the well-maintained paths. Those who prefer to sled or snow tube can check out cosmic tubing at Skibowl’s Snow Tube & Adventure Park.
  • Visit Multnomah Falls during winter when grey days keep the crowds at bay, unlike in the summer season where parking is nearly impossible to find. As Oregon’s tallest waterfall, Multnomah Falls is just 30 miles east of downtown Portland along the Historic Columbia River highway, with both wheelchair-accessible viewing platforms and steep hiking trails that lead all the way to the top.

Winter in Portland also brings some of the lowest hotel rates of the year, both downtown and in some the city’s newest hotels on the East side. So grab your raincoat and gear up for a winter weekend in Portland like the locals do. Forgot your raincoat? Local shops Showerpass, Columbia Sportswear and RAINS have you covered. Alternatively, check out MadeHerePDX for locally made high-quality weather-worthy jackets from local makers such as Ginew, Kiriko and WILD. Of course, all shopping in Portland is tax-free.