: Courtesy of Tyler Roemer

89 Days of Oregon Winter Fun

Make the most of winter with these inspired activities, and collect the trading cards at Travel Oregon Welcome Centers.
January 10, 2024

You might have seen images and video of a talking kayak, beaver, rose, telephone pole, dark sky and pair of boots in your social media feed lately, promoting their favorite activities across Oregon.

These friendly sidekicks are back this winter to show you what’s especially incredible about this time of year — from moonlight snowshoeing and truffle hunting to sleigh rides and fireside winetasting. Much of it can be done with an expert guide, which means you can tackle logistically tricky trips without the hassle of navigation, planning, gear and equipment. Sometimes transportation is provided too. Some of the activities are self-guided, so the blueprint is there for an adventure on your own timeframe.

Either way, these trips are sure to bring wonder and delight during the short 89 days of winter — hardly enough time to experience it all.

Here’s a look at our sidekicks’ top winter activities, each featured in Travel Oregon’s collection of 30 limited-edition trading cards. These cards can be picked up in person (only) at our Travel Oregon Welcome Centers from January 30 through March 15, or while supplies last. Each complimentary wax pack includes seven assorted activity cards, and participants in our sweepstakes (launching January 30) stand a chance to win a complete set of all 30 cards and a $500 gift card for your own guided experience. To enter, fill out the sweepstakes form.

These adventure tips will get you embracing winter in Oregon like a pro. How many will you take on this season?

Hands making beautiful coffee drink with Rosa's playing card displayed to the left of the cup.
Courtesy of Third Wave Coffee Tours


Take a Coffee Tour

Coffee isn’t just a beverage in Oregon. It’s a culture. That much is clear by the more than 200 specialty coffee shops and micro-roasters throughout the state, including around 80 roasters in Portland alone. The cozy days of winter are the perfect time to experience a tour of Portland’s coffee scene through Third Wave Coffee Tours, as guide and owner Lora Woodruff shares her insider knowledge at some of her favorite cafes, roasters and donut shops.

Go Truffle Hunting

Culinary enthusiasts may know that winter is prime time for Oregon’s world-famous black truffles as they ripen in old-growth forests and land on menus sourced by local chefs in the know. If you’ve ever wanted to hunt for these aromatic truffles at their peak, the best way to do it is with an expert guide like Black Tie Tours. You can also visit one of several businesses in Newberg along the Truffle Trail, or grab a seat at the annual competition for truffle-hunting dogs.

Sip Along a Tap Trail

After a long day exploring Oregon’s highest peak, a refreshing beer, balanced cocktail or glass of crisp cider always hits the spot. It’s easy to find the perfect spot for a post-adventure drink thanks to the Mt. Hood Territory Tap Trail. Consisting of over a dozen local craft distilleries, breweries and cideries, this self-guided trail includes a free mobile passport designed to help you discover the bounty around Mt. Hood.

Try Fireside Wine Tasting

About 180 vineyards have taken root in the Rogue Valley AVA, the southernmost in Oregon, stretching from the Rogue River to Oregon’s southern border and situated at the same parallel regions as Spain and Southern France. Winter is cellar season, where visitors can take advantage of the slower pace, sip your new favorite wine and nosh on woodfired pizza at Kriselle Cellars, set on a gorgeous property next to the Rogue River.

Eagles perch in trees with snow packed mountains in the distance. SustainaBill's playing card is right of the tree.
Courtesy of Columbia Gorge Discovery Center


Get Excited for Eagle Watching

During the winter months, migrating eagles from the north swoop southward in search of ice-free hunting grounds on rivers, in reservoirs and along the Coast, joining Oregon’s year-round resident eagles. The Columbia River Gorge, in particular the Columbia Gorge Discovery Center in The Dalles, is an excellent place to watch these magnificent creatures. Time your trip for annual The Dalles Dam Eagle Watch or visit the discovery center for close-up raptor shows.

Go Adaptive Snowboarding

Oregon is a winter playground to all, thanks to the skiing, snowboarding and Nordic skiing lessons available to everyone through Bend-based Oregon Adaptive Sports, from first-timers to seasoned athletes with disabilities. Participants are paired with a certified adaptive instructor and fitted to appropriate equipment. You can find adaptive programs at Mt. Bachelor, Hoodoo and Mt. Ashland.

Book a Sleigh Ride

Revel in old-timey charm with a horse-drawn sleigh ride in historic downtown Baker City. Book your ticket in advance for this hour-long trip through time. Warm up with a hot drink afterward at the historic Geiser Grand Hotel. Rides are offered mid-December through February. Your ticket includes a hot drink afterward in the hotel’s cafe.

Try Backcountry Nordic Skiing 

In Norway friluftsliv, or “the outdoor life,” refers to the concept of unwinding in the open air, no matter what the weather. Nature lovers in Oregon lean into this Scandinavian culture. In Oakridge, join a guided tour with experts from outfitter Cog Wild for backcountry Nordic skiing and snowshoeing near Willamette Pass. Meet fellow winter enthusiasts on a group tour or book a private tour with a guide to experience the magic of winter.

Courtesy of Lan Su Chinese Garden

Telephone Paul

Attend a Lunar New Year Event

Traditionally known as the Spring Festival in many East Asian and South Asian cultures, Lunar New Year marks a period of renewal, prosperity, happiness and good health. Beginning Feb. 10, 2024 visitors are welcome to join in events across the state including the Lan Su Chinese Garden’s two-week Lunar New Year celebration in downtown Portland, ushering in the Year of the Dragon. Enjoy cultural performances, family crafts, traditional foods and more.

Visit the Portland Art Museum

The Portland Art Museum‘s new temporary exhibition “Black Artists of Oregon” (through March 17, 2024) sheds light on Black art. Over 200 pieces highlight and celebrate 69 Black artists who have shaped Oregon’s art scene for generations and inspired countless others artists across the country. The exhibit is considered the first of its kind to consider the work of Black artists collectively in Oregon. All year long, you can see more work by Black artists throughout the city of Portland and the state.

Celebrate 40 Years of the Willamette Valley AVA

Visitors in 2024 have good reason to raise a glass, with a year-long series of events and special wine tastings in celebration of the 40th anniversary of the Willamette Valley American Viticultural Area status. A handful of Oregon’s pioneer winemakers saw a hallmark year in 1984 when the Willamette Valley was granted its official AVA status, thanks to Adelsheim Vineyard founder David Adelsheim. Check the calendar for inspired events all year long throughout the region.

Bundle Up for the Winter Light Festival

The annual Portland Winter Light Festival illuminates the darkness of the winter season with a host of unique and interactive live performances staged around town. Bundle up, don your favorite pieces of glow-flair and plan to join in the range of free, all-ages events between Feb. 7-9, 2024, from fire dancing and lantern parades to pop-up art and fireside storytelling.

Two skiers on rim of Crater Lake raise poles. Boots trading card is displayed to the right.
Courtesy of Main Street Tours


Go Snowshoeing at Crater Lake

Snowshoeing is one of the most delightful ways to experience the outdoors in winter, and Crater Lake National Park is one of Oregon’s most iconic sites. Book a guided Crater Lake snowshoe tour through the expert local guides at Rogue Trotter (formerly Main Street Tours). Visitors can enjoy private shuttle service to and from Ashland, gear rentals, all instruction and peace of mind as they tromp around the snow-covered meadows and forests blanketed with sparkling snow.

Visit the Wildlife Safari

Visit Wildlife Safari in the Southern Oregon town of Winston with a 4.5-mile drive-thru to look at more than 500 animals of 80 species. Wild residents include hippos, rhinos and zebras in the Africa section, with grizzly bears, bison and elk in the American area. The drive offers up-close access to tigers, lions and giraffes among other large wild creatures. Book a special encounter to get up close to the animals or help feed red pandas, tigers and giraffes this winter from a new heated barn.

Be a Kid Again at Cosmic Tubing

What makes sliding down the slopes in a giant tube even more thrilling? How about 600,000 LED lights, laser light shows and rocking music? Grab the crew and try cosmic tubing at Mt. Hood Skibowl, and know that midweek is the best time to visit if you want to avoid some of the crowds. Book a room nearby for the best experience. Before you head to the mountain be sure to check TripCheck for weather and road conditions and be comfortable driving in winter conditions.

Try Rock Climbing

Smith Rock State Park is the birthplace of American sport climbing, and if you’ve always wanted to check it out, there’s no time like the winter when it’s cooler and quieter. You’re in good hands with an experienced outfitter like Chockstone Climbing Guides, run by Jim Ablao, a legend in the industry. You can take an intro-to-climbing session, a family session or a custom group trip for your adventurous posse. Then enjoy a cozy stay with friends afterwards in nearby Sisters, Bend or Redmond.

Man points to tracks in the sand. Kayakyak's card is displayed to the left.
Courtesy of Wavecrest Discoveries


Take a Guided Dune Walk

Experience one of the Oregon Coast’s most spectacular landscapes on foot with a guided adventure. Wavecrest Discoveries, based on Oregon’s South Coast, offers a half-day dunes exploration tour that combines various short hikes in different dune environments (for about 2 miles of walking) to help you experience the range of plant and animal ecosystems and the high drama of the dunes formations.

Access the Beach

Oregon’s 363 miles of public coastline are for everyone, no matter your mobility. The nonprofit David’s Chair helps to make that happen with 2-hour access to all-terrain track-chairs to access the sandy shoreline. These are available and bookable year-round at fixed sites in Manzanita, Seaside, Netarts, Pacific City, Newport, Florence and Gold Beach. Visitors can also reserve David’s Chairs through its Tow ‘N Go program, to pick up the chairs near Medford and Tigard and tow to their outdoor location.

Cozy Up for Storm Watching

One of the coziest ways to enjoy the blustery season in Oregon is to watch the high winter waves from the safety of a designated viewpoint, or better yet, your hotel balcony or waterfront dining room while sipping a warm beverage. Several places on the Oregon Coast are ideal for storm watching. On the South Coast, you can head to spots like Shore Acres State Park near Coos Bay or Chetco Point Park in Brookings. Wherever you go, be sure to abide by all signage.

Enjoy Riverside Dining

Sometimes you want to shop, taste and dine at your own pace, and the Great Oaks Food Trail is one of those sweet spots to do just that. Weaving through the communities just west of Salem, conveniently off Interstate-5, you can check into The Independence hotel to recharge with views of the Willamette River. Grab a small bite or glass of wine at the hotel’s restaurant, Territory, then find bakeries, candy shops, wine bars and more along the self-guided food trail within a few minutes’ walk or drive.

Group of people look up at dark night sky. Darksky's playing card is displayed to the right.
Courtesy of Wanderlust Tours

Dark Sky

Try Moonlight Snowshoeing

If you’re looking to level up your snowshoeing experience to experience the winter wonderland by nightfall, book an adventure with Wanderlust Tours in Central Oregon. Naturalist guides will impart their knowledge of the wildlife that call the Cascade Mountains home and will have you and your family running, jumping and splashing through powder. The Moonlight & Starlight Snowshoe Tour and others are open to all ability levels and are recommended for children 8 and older.

Find Bliss with Hot Springs and Stargazing

Take the chill off with a soak in the 2 million gallons of mineral-rich hot springs at Hot Lake Springs Resort, one of the largest hot springs in the Northwest. Book a cozy winter getaway or snag a day pass for a visit during a road trip along Interstate-84. The five lakeside soaking pools are open year-round but are extra cozy in the cooler months, when the nights are longer and you can stargaze for hours. A pub and 60-seat movie theater are on site for the full retreat experience.

Book a Backcountry Ski Tour

If you’re a hardy soul looking for the ultimate winter adventure, consider an overnight ski trip in the Wallowas. Eagle Cap Mountain Guides offers guided and catered trips between mid-January and mid-March, ideal for groups of six to eight people. Led by a professional guide, you’ll ski by day and make your base camp at night at a 20-foot yurt and wall tent in a snowy forest, perfect for sharing hearty meals and sharing stories.

Make Time for Winter Glamping

While many choose to hunker down at home or bask in the warmth of a fireplace during winter, Oregon State Park cabins and yurts offer a welcoming alternative. With greater availability and the comfort of heating and electricity, these accommodations provide a safe and welcoming way to experience the natural world during a different season. Make sure to equip your car for winter weather and drive cautiously, especially on icy roads and bridges.


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.