What to Do in Oregon in December

Hop aboard the Holiday Express, hunt for ornaments in the Willamette and Umpqua National Forests, and more

By Portland Monthly Staff November 30, 2021

The Holiday Express in Southeast Portland

Hopefully your turkey leftovers are behind you. Now, let's just power through the holidays. (Need help with a gift? Check out our 2021 guide here.) But in between checking names off your holiday shopping list, make sure to set aside time for fun.

These events around Oregon will help you ring in the winter season and jumpstart your holiday spirit.

Christmas Ship Parade

Christmas Ship Parade

December 3–21, Willamette and Columbia Rivers, free

This almost 70-year-old Oregon tradition started with a lone sailboat parading along the Columbia and Willamette Rivers. But today, the annual Christmas Ship Parade averages some 55 to 60 vessels, decorated and done up with lights, ribbons, sirens, and all things festive. Most nights this seasons will have separate fleets on the two rivers, but for six nights this year they will have a combined fleet with more boats in one location. Peep a schedule here to see when the parade will hit your part of town.

Clackamas County Winter Fair

December 3–24, 694 Northeast 4th Avenue, Canby, OR, $0–15

Take a trip down south to Canby for its second annual Clackamas County Winter Fair. From December 3 until Christmas Eve, marvel at the 200-foot building light display, wander through Santa’s Village (and take pictures with the jolly old man himself every evening until 9 p.m.), enjoy tree light displays, and more. Children 10 and younger get in for free, and food and beverages will be available for purchase.

Kick off the winter ski/snowboarding season at Mt. Hood Meadows

Celebrate the Season at Mt. Hood Meadows

December 11, 1 p.m. & 3:30 p.m., 14040 Hwy 35, Mt Hood, $35

Maybe you tried Mt Hood Meadow's new trail system and loved it. (We did.) But we know why you're here. You want the white stuff. Now it's back, and so is Mt. Hood Meadows, which is kicking off its winter season with its Celebrate the Season event, an exclusive beer tasting event with brewers from Hood River-based pFriem. Held in Vertical, the resort's full-service restaurant and bar, there will be two beer tasting events at 1 and 3 p.m., with live music and snacks. 

Aboard the Holiday Express 

The Holiday Express

Now through December 19, The Oaks Station, 7806 SE Oaks Park Way, $16–80

Southeast Portland residents might be hearing a different train horn than that usual blasted metal beast on Division, always holding up traffic and going backwards for no dang reason. This “other” train is significantly cooler and much cuter. It’s the Oregon Rail Heritage Center’s annual Holiday Express train. Bring the family and ride on vintage rail cars, decorated with garland, ornaments, and lights, along the Willamette River in Southeast. Santa and his elves, of course, will also be on board. Dress warmly and wear your masks—it acts like a scarf anyway.

Mount Hood Christmas Train

Now through December 26, 110 Railroad Street, Hood River, $50–70

Feel like meeting jolly ol' Sandy Claus out in the snow? Take a trip out to Hood River for the annual Mount Hood Christmas Train. Every year the Mount Hood Railroad, a centuries-old short line railroad offering round-trip excursions in Northern Oregon, transforms its trains into delightful Christmas carriages, where opportunities abound to meet Santa and his little helpers. From now until December 26 the Christmas Train will take weekly tours around the area. Masks are required aboard the train. 

Hike around the Willamette and Umpqua National Forests for a chance to find one of 200 ornaments hidden in the area. 

Willamette Valley Forest Ornament Hunt

 Now through January 1, 2022, free

Some people go on a hike and take back rocks or sand or mushrooms. If you go hiking around the Willamette and Umpqua National Forests this time of year, you can take back an Oregon diorama ornament. No, these ornaments don't grow naturally in the forest. They've been placed there (200 to be exact) by the Willamette Valley Visitors Association, which has been putting on the annual Ornament Hunt for four years. Find one (just one; leave some for others, dude) and it's yours to keep. For full contest rules and details, click here. Happy hunting!

Zoo Lights at the Oregon Zoo

Zoo Lights

Now through January 9, 2022, 4001 SW Canyon Rd, prices vary

Bust out the dusty windbreaker from the coat closet, we’re going to the Oregon Zoo for its annual ZooLights, when the whole place is decked out in gorgeous animal-themed lights. This year, the Oregon Zoo's traditional walk-through Zoo Lights experience is back, but its drive-through experience, implemented last year to address COVID-19 concerns, will also be available for a few nights (December 1, 2, 7, 8 & 9 and January 4, 5 & 6, 2022). Food and drinks will also be available this year. 

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