Oregon Trails

An Illustrated Guide to Oregon’s Winter Celebrations

Must-catch happenings during the state’s coldest months.

By Brooke Jackson-Glidden Illustrations by Jordan Kay December 1, 2025 Published in the Winter 2025/2026 issue of Portland Monthly

Image: Jordan Kay

Portlanders tend to hibernate when the rainy season begins. Things get colder, and a book near the fireplace beckons. But consider hopping in the car for a chilly seasonal excursion—perhaps to catch an illuminated Elsa in Southern Oregon, or to sample sausages in a Bavarian-style village, or to watch a bald eagle dive into the Columbia. Below, an illustrated sampler platter of options.


Umpqua Valley Festival of Lights

Image: Jordan Kay

Nov 23–Jan 1

Roll through Roseburg’s River Forks Park for a drive-in holiday light extravaganza—think glimmering scenes of Santa stomping wine grapes or Frozen’s Elsa kiki-ing with Olaf. An on-site holiday village covers the cocoa and Santa meet-and-greets.

Eagle Watch

Image: Jordan Kay

mid to late January (depending on migration patterns)

Each winter, migratory bald eagles settle into a quiet green patch on the south side of The Dalles Dam, where they roost and enjoy the Columbia’s wriggling river fish. The dam’s visitor center welcomes their return with a week of bird-watching—scopes and bird nerds (read: park rangers) provided.

Mt. Angel Volksfest

Jan 30–Feb 1

Image: Jordan Kay

“People’s festival” in German, OG volksfests typically involve beer, wine, and carnival rides. Mt. Angel’s version is a German sausage–fueled bacchanal in which lederhosen-donning locals dance, drink, and sample a daunting array of wursts.

Oregon Truffle Festival

Image: Jordan Kay

February

A monthlong, statewide celebration of Oregon’s most treasured subterranean fungus, complete with truffle tasting, truffle dog training, mushroomy dinners, and cooking classes. Kicks off with the Joriad North American Truffle Dog Competition, a canine-assisted fungi hunt across the Lane County Fairgrounds.

Bend WinterFest

Feb 13–15

Image: Jordan Kay

Central Oregon’s chilly music festival involves far more than bands—last year, ice sculptors mingled with snowboarders and skiers preparing to catch serious air at the Pump Bump Jam Contest, a gnarly snow sport exhibition.

Newport Seafood & Wine Festival

Feb 19–22

Image: Jordan Kay

In 1977, as Oregon’s wine industry was just starting to get legs, Newport hosted its inaugural NSWF to bring tourists to the coast during its slow season. The festival is now the coastal town’s biggest bash—and the longest-running wine competition in the Pacific Northwest.

The FisherPoets Gathering

Image: Jordan Kay

 Feb 27–Mar 1

Seafaring bards from across the country pack their journals and acoustic guitars to descend on Astoria, performing original poetry, prose, and music inspired by years in the fishing industry. Started back in 1998 as a reunion of commercial fishers-turned-wordsmiths.

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