: Cooper Spur Mountain Resort by Gregor Halenda

Top Things to Do in Oregon This Winter

Plan a trip to discover the season’s best-kept secrets.
November 27, 2017 (Updated December 2, 2019)

Winter in the Pacific Northwest means impossibly gray skies and the ever-present trickle of rain, right? Well, not exactly. It’s a common myth that’s easily debunked when you consider Oregon’s sheer geographical diversity: Sunny high desert? Check. Snow-laden forests? You bet. Pristine rivers? Pack your fishing gear. Mountain resorts for downhill skiing? Some of the best in the world. Hmm, maybe that misconception is really a clever way to keep the season a secret? Either way, the secret’s out: Cool days, fluffy snow and fewer crowds make winter prime time for visiting some of Oregon’s most spectacular sights.

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Oregon’s diverse climates and landscapes mean that winter looks completely different, depending on where you go. Whether you’re hunting for champagne powder in the Wallowas or truffle hunting and puddle jumping in the Willamette Valley, Oregon winter means diverse adventures.

By Gregor Halenda

Cooper Spur Mountain Resort

While skiers flock to Timberline Lodge and Mt. Hood Meadows, families with young kids head to Cooper Spur Mountain Resort. Stay in snug log cabins and enjoy convivial, locally sourced meals and drinks at the on-site Crooked Tree Restaurant & Tavern. Reasonable lift tickets are a big draw at the resort’s ski area. For the 2019-20 season, ticket prices for adults run $37 and children under six are free. (Check ahead as ticket prices can change from year to year.)

By Leon Werdinger

Fossil hunting

Summertime highs of nearly 100 degrees Fahrenheit mean that winter is the perfect time of year to see Eastern Oregon’s fossil beds, where animal and flora remains can be up to 7 million years old. You can even dig for fossils on the grounds of Wheeler High School in the perfectly named town of Fossil. On your way there, stop and look at the striking, striated mounds of one of Oregon’s seven natural wonders, the Painted Hills.

By Robbie McClaran

Chocolate shops

You’ve attended a coffee cupping and hit more breweries than you can count. What’s else to taste? Try a tour of Portland’s artisanal chocolate shops — a perfect way to get a glimpse of the city’s craft resurgence. Boundary-pushing chocolatiers such as Cloudforest Chocolate and Creo Chocolate offer factory tours and tastings. Boutiques such as Cacao and The Meadow peddle a wide selection of both local and imported sweet treats.

Courtesy of Bandon Dunes Golf Resort

Coast golfing

In the winter, greens fees are reduced by as much as half. It’s the perfect time of year to check out the famously beautiful golf courses set along Oregon’s rugged coastline, such as Bandon Dunes Golf Resort and Gearhart Golf Links, the oldest golf course in the Northwest. These resorts are also some of the most comfortable places for another traditional Oregonian winter pastime: marveling at the spectacular crashing waves of a winter storm.

By David Cooper

Oregon Shakespeare Festival

Ashland is surrounded by plenty of natural attractions; it’s also one of the only places where you might overhear “Henry IV” being enthusiastically quoted while you wait for sushi. Every year more than 100,000 people descend upon Ashland for the Oregon Shakespeare Festival, which kicks off its annual season with opening-weekend festivities each February. Afterward, refresh your senses with a soak in Ashland’s famous mineral waters at Chozu Bath and Tea Gardens or Lithia Springs Resort.

Lower South Falls

Waterfalls and wine

Wine and wilderness are two of the major attractions of the Willamette Valley, and winter (aka Cellar Season) is the ideal time to experience both. You’ll avoid the crowds that clot the state’s beautiful parks in the summer, especially at each of the 10 stunning waterfalls at Silver Falls State Park. Meanwhile, you’ll have many wineries to yourself, no matter what touring route you choose. (Call ahead, as many wineries offer limited hours or open only by appointment during winter.)

By Nickie Bournias

Bend Nordic adventures

Bend, which has one of the longest ski seasons in North America, is home to a multitude of beautiful cross-country snowshoe and ski trails. The Meissner Nordic and the Central Oregon Nordic clubs maintain many community trails (some with warming huts!), or bring your delighted four-legged companion to the dog-friendly Wanoga Snow Play Area Sno Park.

The Grotto courtesy of Waz-Mix-Pix

What’s happening

Festival of Lights (Nov. 29-Dec. 30, 2019): The Grotto, Portland’s stunning outdoor church, throws a yearly Festival of Lights, which starts after Thanksgiving and runs through December 30. It’s the largest Christmas choral festival in the world — featuring nearly 160 school, church and civic choirs, and it has a petting zoo for the little members of your family. (Check the website for choral schedule and tickets.)

Whale Watching Week (Dec. 27-31, 2019): Every winter around 20,000 gray whales travel from Alaska to their breeding grounds in the warm waters of Mexico. It’s the majestic migration of the great grays. While they’re visible from many places on Oregon’s coastline, one of the best ways to secure a spotting is to visit Depoe Bay’s Whale Watching Center during Whale Watching Week, held the last week of December.

Oregon Truffle Festival (Jan. 23-26 and Feb. 14-16, 2020): The Willamette Valley’s Oregon Truffle Festival is one of the most decadent culinary experiences in the nation. Truffle hunters, vintners and world-famous chefs and restaurateurs hold events, workshops and fabulous meals to celebrate this rare and delicious tuber.

The Eagle Cap Extreme (Jan. 22-25, 2020): The Eagle Cap Extreme is a series of rugged and exciting sled-dog races ranging from 20 miles to 200 miles that take place in late January in the Wallowa Mountains. It’s the only Iditarod-qualifier race in the Western states.

Oregon WinterFest (Feb. 14-16, 2020): Bend is one of the few places in the country where you might find a snowboarder casually executing a rail grind downtown, right next to where you park your car. Oregon WinterFest is Bend’s largest festival, with ice sculptures, live music and plenty of food and beverages — both hot and cold — from many of Central Oregon’s best wineries, breweries and restaurants.

FisherPoets Gathering (Feb. 28-March 1, 2020): Deckhands, skippers and cannery workers gather in venues all over Astoria to tell their stories in prose, poetry and song during the FisherPoets Gathering, a yearly literary festival in celebration of the commercial fishing industry.

Portland International Film Festival (March 6-15, 2020): If you think that winter is the best time of year to huddle inside a dark, warm movie theater and travel the world through the silver screen, you are correct. Pick one — or several — of the nearly 100 exciting new feature films and short films that will be screened during the Portland International Film Festival, the largest film festival in the state.

If you go

Many roads close in winter due to ice, wind and snowfall, especially in the Gorge and in Eastern Oregon. Visit TripCheck.com to check road conditions and carry basic winter car-safety gear such as a blanket, chains, a small shovel and flares. Wherever you go, follow these Leave No Trace tips.

About The

Adrienne So
Adrienne So is a gear, travel and lifestyle writer based in Portland. Her work has been featured in Wired, Slate and Cool Hunting, among other publications; her beverage writing has appeared in The New Brewer, All About Beer and Sip Northwest. When she's not camping, climbing or drinking beer, she is hanging out with her husband, daughter and two dogs.

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