While most buckle up for winter, Portlanders are just getting started. Portland in winter means lazy afternoons at your nearby bookstore or coffee shop while listening to the sound of raindrops pattering outside. It means hikes in the forest park that are sure to have your every moment enjoying yourself, but somehow you seem to be timing it perfectly before the rain sets in. It means trips to Mount Hood, where you can ski all day at three major ski resorts and easily return to Portland for happy hour prices at local breweries. Winter in Portland also means more restaurant availability to enjoy the season’s root vegetables in the best spots in town.

Some of our favorite activities for rainy days are …

Restaurants with seasonal menus:

  • The menu at Picturesque, a cozy restaurant with exquisite cuisine, perfect for every occasion, changes seasonally with ingredients from the region. Chef Ryley Eckersley takes the best offers of each season and turns them into beautiful plates, skilfully paired with one of the delicious cocktails on his seasonally inspired cocktail menu.

  • Is behind it Eventually PDX, Ruthies The food cart serves a seasonal menu based on recipes from co-owner Collin Mohr’s grandmother, Ruthie, and ingredients from the region. Across the menu, you’ll find pickles, jams, and canned foods that use pickling and canning techniques inspired by his grandmother.

  • The menu in the newly opened Wild north is based on sustainability and full taste profiles. All ingredients are fully integrated into the menu so nothing is wasted. With dishes cooked entirely on a wood grill, the menu changes seasonally to present new offerings based on what is fresh and local at the moment.

Make yourself comfortable in a bookstore:

  • Opened June 2021, owned by black Third Eye Books is the leading supplier of books, accessories and gift items with a focus on Africa in the greater Portland area. Owners Michelle Lewis and Charles Hannah have curated a wide variety of thought-provoking bestsellers and lesser-known books to help raise awareness of African-themed books and anti-racist literature in the community.

  • A visit to Portland is complete without a trip to Powell’s books, the world’s largest independent bookstore, which happens to be 50 years old in 2021. Its flagship store in Portland’s Pearl District occupies an entire block of town and offers 68,000 square feet of used, new, rare, and out of print books. To celebrate this milestone, Powell’s Books published his 50 books for 50 years. The collection is a self-reflective curation that reminds everyone to “act as a mirror and a beacon”. However, the never-ending book recommendations at Powell’s Books come from the popular “Staff Picks” cards that can be seen in the aisles – each card is like a personal note from a Portlander. Welcome to our city and the books 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 the traditional wine country with the opening in July 2020 Crick PDX. A visit to this hip-hop themed tasting room will brighten up any winter day in Portland with Abbey Creek wine from Faustin’s White Plains Winery.

  • George Johnson, founder, chief brewer and pizza maker Assembly brows on a craft brewery dream in the neighborhood aimed at guests aged 21 and over. Johnson, the first African American to own and operate a brewery in Oregon, welcomes visitors to the up and coming Foster-Powell neighborhood with its Detroit roots, own batter recipe, and accessible craft beer.

  • Opened July 2021, Church tower brows is perhaps one of the most impressive breweries to open in Portland last year, home to an impressive 110-year-old church known for its ornate steeple, long history, and incredible stained glass. Guests enjoy a rich selection of ales and lagers, complemented by upscale pub fare, while dining on traditional pews.

Outdoor activities – rain or shine:

  • With 70 miles of hiking trails, aptly named Forest park is a popular retreat for runners, riders and hikers. This eight-mile nature reserve in the northwest corner of the city is one of the largest urban parks in the country and offers locals and visitors alike a break from urban life. Check out the popular Macleay Park and Wildwood walking trails, both of which wind around the famous Pittock Mansion.

  • Mount the hood lies in the footprint of the city of roses and offers a spacious winter playground just 90 minutes from the city center. For skiing and snowboarding, Mount Hood Meadows, Mt. Hood Skibowl, and Timberline are great options. Cross-country and snowshoe trails zigzag across the mountain and allow outdoor enthusiasts to reconnect with nature on the well-groomed trails. Those who prefer sledding or snow tubing can try out cosmic tubing in the Snow Tube & Adventure Park at Skibowl.
  • visit Multnomah waterfalls in winter, when gray days keep the crowds in check, unlike in the summer season, when parking spaces are hard to find. Multnomah Falls, Oregon’s tallest waterfall, is just 30 miles east of downtown Portland along the Historic Columbia River Highway and has both wheelchair-accessible viewing platforms and steep hiking trails that lead to the top.

Winter in Portland also features some of the lowest hotel rates of the year, both in downtown and some of the city newest hotels on the east side. So grab your raincoat and gear up for a winter weekend in Portland like the locals do. Did you forget your raincoat? Local shops Shower pass, Columbia sportswear and RAIN have you covered. Alternatively, stop by MadeHerePDX for locally made high quality weather jackets from local manufacturers such as Ginew, Kiriko and WILD. Of course everything Shopping in Portland is tax free.