: Cooper Spur Mountain Resort by Gregor Halenda

Top Things to Do in Oregon This Winter

When conditions allow, plan a trip to discover the season’s best-kept secrets.
November 27, 2017 (Updated December 27, 2022)

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.

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 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 runs April-October. 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 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 and snowshoe 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

Be Prepared

Oregonians know that winter weather here can change in a minute, so always check road conditions on TripCheck.com before you go. If you know how to drive in the snow (you know who you are), make sure to carry chains and know how to use them. Or, invest in snow tires for the season. See the Oregon Department of Transportation’s tips and handy videos on everything related to winter driving. (Don’t be that person caught on the TV news sliding down an icy hill.)

Whether you’re heading to a winery or hiking trail, it’s always a good idea to call ahead to your destination to confirm accessibility and conditions — avoid hiking when conditions are icy. Know that even if a trail or road is technically open, it may not be maintained, so check with the U.S. Forest Service ranger district or look for alerts on the Oregon State Parks and Recreation website if you’re not sure.

Winter is a great time to consider leaving the car at home and traveling by shuttle, train, ride share, public transit or another mode. Find car-free trip ideas to Mt. HoodOregon’s North Coast and Central CoastBendWillamette Valley wine country and the Columbia River Gorge.

If you are driving, load up a full tank of gas, printed maps (available at Oregon’s Visitor Centers) and extra water, snacks and supplies (such as medication) in case of a weather-related emergency.

When it comes to winter clothing in Oregon, it’s just like a good cake: layers. Fleece, wool and Gore-Tex are your friend, and don’t forget your hats, gloves and weather-proof shoes. Check out shops such as REI (eight locations in Oregon), Next Adventure (in Portland) and other local outdoor retailers.

And know your limits when you head outdoors. Book a guided trip or tour if you want to be well taken care of or if you’re a beginner.

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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