: NashCO Photo

Winter Trips in the Portland Region

October 21, 2019

Creativity isn’t just nurtured in the Portland Region; it’s a way of life. From its homespun craft beverages (coffee, tea, kombucha, beer, wine and spirits) to its nationally lauded food scene (known to be more accessible and affordable than larger cities), Portland and its nearby communities inspire wonder all year long. In winter, the Portland Region comes alive with festive and creative holiday traditions for all ages and interests, from artisan gift fairs and art walks to light shows and tasting events. You don’t have to leave the city for an awe-inspiring nature retreat — Forest Park, the largest urban nature park in the United States, is evidence of that. But just beyond the city’s borders — in the verdant agricultural valleys of Forest Grove, Hillsboro, Gresham, Oregon City, West Linn, Scappoose and other areas just east, west, north and south of Portland — you can see winter wildlife at its most active; and cool, misty trails at their least crowded. You can even get there without a car, if you so choose. Grab your thermos, hiking boots, maps and reading material and hop aboard the Portland Region’s accessible light-rail system for an unforgettable trip this winter. 


Pioneer Courthouse Square tree lighting

Destination Downtown

Downtown Portland is a vibrant hub of shopping, dining, parks and performance halls, and it can be explored easily on foot, by bike or by scooter. The compact, walkable blocks from the Willamette River west to the hills and north of Burnside to Old Town/Chinatown, the Pearl District and the Northwest Alphabet District are constantly buzzing with energy. From Pioneer Courthouse Square near the elegant 19th-century courthouse, a stroll along the leafy South Park Blocks leads past the venerable Portland Art Museum and the classic Arlene Schnitzer Concert Hall, one of five venues that make up Portland’5 Centers for the Arts. Farther east, Tom McCall Waterfront Park offers a path for walkers and runners along the lazy Willamette River. Powell’s City of Books, the world’s largest independent bookstore, houses a full city block of titles for browsing and frequent readings. The hip West End and Pearl District are a shopper’s paradise, with scores of unique boutiques for gifts. And you could spend weeks here at a different hot spot each day — try the eclectic chef-driven eateries at the indoor Pine Street Market and hop on a BIKETOWN bike or e-scooter to travel 2 miles northwest to the the hip Slabtown location of Breakside Brewery for award-winning IPAs. Hop in a rideshare to travel 3 miles north to funky North Portland, where Ex Novo Brewing Co. and many more standout breweries are ideal for sipping on a drizzly day. Downtown revelers can also witness the lighting of the 75-foot tree at Pioneer Courthouse Square just after Thanksgiving, the free annual tuba concert and the cheery Holiday Ale Festival in December.

Iron furnace at George Rogers Park (Photo by: mthoodterritory.com)

Urban Nature Retreats

In Portland you don’t have to go far to feel like you are out of the city and into the wild. Forest Park — one of the largest urban parks in the nation — offers 5,200 acres/2,104 hectares of grand old trees, meadows and wildflowers. Thanks to a brand-new pedestrian bridge, Barbara Walker Crossing, Forest Park’s iconic 30-mile/48.3-kilometer Wildwood Trail just became even more of a vital and accessible link for nature lovers in the city. Just north of the city, time seems to stand still at the Scappoose Bay Marine Park Nature Trail, a haven for wildlife and migratory birds. Soak up the tranquility with a brisk two-hour guided winter wonderland kayak tour. Sauvie Island is also a birding oasis, with thousands of snow geese, Canada geese and more flocking here in the winter months. Amateur birders are welcome to join in Portland Audubon’s annual Christmas Bird Count in December. Just south of Portland, Lake Oswego’s George Rogers Park stretches across 26 acres/10.5 hectares with river access, picnic areas, walking trails and the historic “Iron Furnace,” a testament to the region’s industrial past. Mary S. Young Park in West Linn is a draw for ample birdlife on the wooded trails and also features a large off-leash area for canine day-trippers. In Hillsboro, Cooper Mountain Nature Park is an oasis of family-friendly trails that wind through Oregon white oaks; if they’re not tired yet, there’s a nature play area with supreme views of the Chehalem Mountains and Tualatin Valley below. Orenco Woods Nature Park is a designated regional trail that allows dogs on leash, with giant woven structures in the children’s nature play and an arched bridge that overlooks the wetland below. Just west of Hillsboro, Forest Grove is a major gateway to the outdoors, with stunning trails for hiking, biking and wildlife watching year-round. Try Hagg Lake (which is popular in the summertime with fishers, boaters and paddlers) and Fernhill Wetlands, a winter birding hotspot at the confluence of Gales Creek and the Tualatin River. See thousands of migratory birds as well as beavers and waterfowl from short trails and viewing spots. 

Chinese New Year at the Lan Su Chinese Garden

Car-Free Trips

It’s easy to take a day trip from Portland by MAX train, knowing that you won’t have to deal with traffic, navigating or driving in winter road conditions or parking. You can start downtown at Lan Su Chinese Garden, which marks the Chinese New Year with lion dancing, food and other events for 15 days between January and February. (In December, try to book a seat at the Russian Tea experience at downtown’s Heathman Hotel — a year-round favorite that’s especially festive for the holidays.) Just after Thanksgiving to just after New Years, hop on the MAX to the Oregon Zoo to see the animals and twinkly lights from a winter train right at the annual ZooLights event. In February, take the MAX to Portland’s east side for the free, spectacular Portland Winter Light Festival, hosted at OMSI. Looking for tasty food cart fare in a covered, indoor space with a beer garden? Beaverton’s BG Food Cartel, open year-round, is a quick trip west on the Red Line, with 30 carts to choose from. About 30 minutes west on the Blue Line, downtown Hillsboro’s walkable Main Street is an enclave of boutique shops, galleries and museums. Join in the First Tuesday Art Walk year-round to meet the artists. Traveling east on the Blue Line to Gresham, stop at Tsuri Island, Gresham Japanese Garden to breathe in the solace of the quiet season, as the reds and yellows appear to pop below a dusting of snow or covering of ice. For the panoramic views that charmed early settlers, view six mountains from Hogan Butte Nature Park, or walk the streets of Gresham for original painted art that highlights historic events. A dozen original life-size bronze statues add to the pioneering experience. South of Portland, take the Orange Line to Milwaukie for a wintertime walk along the Willamette River at Milwaukie Riverfront Park. In Oregon City, explore the history of Oregon’s pioneers through exhibits at the Clackamas County Historical Society, and go for a free, guided tour of the McLoughlin House, nearby— a National Historic Site that was the home of “Father of Oregon” John McLoughlin in 1846. Also heading south, the Green Line to Clackamas takes you to the heart of Portland’s Latino-food scene, Portland Mercado, with nine vendors and nine indoor businesses serving up everything from homestyle mole and arepas to fresh fruit, coffee, beer, produce and salsas to go. Find more day-trip inspiration with these MAX trips from Portland. 


If You Go:

Portland is a beehive of activity in the winter months, so it’s often best to travel car-free. Public transit (bus, light rail and streetcar) is well maintained and continues through all weather, including light-rail service to and from Portland International Airport. Options abound for car-share, bike-share, scooter-share and even pedicab services. 

A fantastic way to see the city is by guided tour. Get an insider’s exploration of the craft-beer scene (doughnuts and coffee, too) through Brewvana, Portland Walking Tours or another outfitter. Or see the city from a cozy, heated seat on a riverboat while aboard the Columbia Gorge Sternwheeler or the Portland Spirit (try a sunset, karaoke or Bigfoot-themed cruise!). Bring your raincoat and umbrella to Portland in the winter, or pick one up here at ShedRain, Columbia Sportswear or any REI Co-Op location. 

Downtown Portland

Nature Retreats

Portland, Scappoose, Lake Oswego, West Linn, Hillsboro, Forest Grove

Car-Free Trips

Portland, Beaverton, Hillsboro, Gresham, Milwaukie

About The

Jen Anderson
Jen Anderson is a longtime journalist and travel writer/editor who is now Travel Oregon’s Content & Community Manager, helping to align content for visitors via social media, print and web. She’s called Oregon home for 25 years and loves finding the latest places to eat, drink and play around the state with her husband and two boys. Brewpubs, beaches and bike trails top the list.

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