The Ultimate Portland Winter Bucket List


It’s that time again! Time to embrace the chill in the air and get those kids out of the house for some fantastic, family-friendly events and activities to keep you busy throughout the PNW winter months. Bundle up and head out with this Portland Winter Bucket List!

PDX Winter Activities Events

1. Tubing on Mt. Hood

Pack up the snow gear and head to the mountain! The classic daytime tubing is perfect for the tubing purists, and for the adventurous set there is nighttime Cosmic Tubing, complete with 600,000 LED lights, laser light shows, black lights, colored lights, rock music and more! Most hills are open now! Want to go tubing, snow-less? Check out the Oregon Garden in Silverton!

2. Ice Skating

Strap on some skates and attempt that triple salchow, or just a shaky spin, with options for indoor and outdoor local ice skating centers:

Not feeling the ice? Go roller skating at Oaks Park during their holiday hours (open Thanksgiving, Christmas Eve, and New Years Eve!)

showlovefillneeds43. Volunteering/Giving Back

This is the time for the whole family to lend a helping hand to those in need. There are many organizations that are in need of assistance during the winter and throughout the year both in person and by donations. The winter season is a great time to get started giving back:

4. Portland Hipster Santa

Men with bellies that shake like a bowl full of jelly are a dime a dozen during the holiday season, but luckily Portlanders have the one and only “Portland Santa,” (aka “Hipster Santa”). Portland Santa returns to Pioneer Place this year, complete with his Portland Airport carpet sofa, and is ready for his close-up with the kiddos every Thursday, November 29 – December 20.

5. Pittock Mansion’s Hobbies and Pastimes

This historical Portland home turned museum decks it’s halls every holiday season. From opera to knitting to beekeeping, this year’s Pittock Mansion Christmas will highlight some familiar and not-so-familiar hobbies and pastimes. See the Mansion in a whole new light as volunteer decorators creatively transform rooms into a hobbies and pastimes holiday extravaganza. November 19 -December 31, closed on Christmas day.


6. Christmas time at the Pioneer Courthouse Square

Get into the spirit with all the fun holiday events downtown at the square. Kick off the holiday season with the lighting Portland’s 75-foot Douglas Fir tree the day after Thanksgiving, the Holiday Ale Fest on December 28 (21+), and Mondays on the Mall holiday festivities through New Years! 

7. Local Holiday Events and Tree Lighting Ceremonies

Almost every town center celebrates the season with their own local events and tree lighting ceremonies! Check out your local city website for more information on dates/times:

8. ZooLightswinter

A staple of the season, The Oregon Zoo’s annual, fantastic display of a million and half twinkling lights throughout the zoo and a train ride to boot! The day after Thanksgiving – January 1.  

9. Christmas in the Garden

The Oregon Garden, located in the charming historical town of Silverton, pulls out all the stops for a Christmas extravaganza that includes a tram ride, ice skating, a traditional German market, snow-less tubing, and a glittering light display. The day after Thanksgiving – January 1.

10. Cinnamon Bear Cruise

Inspired by the 1937 holiday radio series, the Cinnamon Bear Cruise takes to the river on the Portland Spirit for a 2-hour cruise. Enjoy treats and character storytelling, music, and magic nightly from The weekend after Thanksgiving – December 26. 

winter11. Winter Wonderland at PIR

Boasting the “Largest Holiday Light Show West of the Mississippi,” Portland International Raceway puts on a spectacular drive-through light show that runs November 23 – December 26. 

12. Trains! Trains! Trains!

There is just something magical about trains around the holidays. Bundle up on hop on for a ride that will be fun for the whole family starting the day after Thanksgiving!

  • Holiday Express Train – Join Santa Claus and his elves for a magical ride behind Portland’s famous steam locomotive. Leaves from Oaks Park.
  • Polar Express – Recreate the magic of the children’s book and feature film, The Polar Express, by dressing in your best pajamas for a festive ride on the Polar Express Train Ride via the Mount Hood Railroad.
  • The Candy Cane Express – A festive steam-powered excursion on the Oregon Coast Scenic Railroad! Visit with Santa while enjoying cookies and hot cocoa. This train is decorated with lights and holiday decorations of the season. Departs from Garibaldi on the north Oregon coast.

13. Dickens Carolers

Enjoy the sounds of the season from the Dickens Carolers throughout the month of December while they stroll around Portland at many public events, including historic McMenamin’s properties! Check their website for specific locations and dates.

14. Christmas in Dairyville

Every year this tiny replica frontier town at Alpenrose Dairy is transformed into a winter wonderland with the nostalgic Storybook Lane, complete with animals, vintage storefronts, local choir singing, Santa visits, and holiday movies in the Opera House. All December until Christmas Eve. 

15. Take in a Show

Get all gussied up for an afternoon/evening out on the town with your budding thespians or dancers.

winter16. Gingerbread Jamboree at OMSI

Have some sweet teeth in the family? Enjoy gingerbread house decorating and the huge candy buffet at OMSI for their annual Gingerbread Jamboree. The best part is no clean up required! November 17 – January 1.

17. Jingle Bell Run/Walk

Get out in the fresh air for a festive run/walk in downtown Portland, always the first weekend in December. Ugly sweaters encouraged!


18. Ariel Tram Winter Holidays

Take in the panoramic views from the Portland Ariel Tram on December 9, 11 a.m. to 3 p.m. Activities include family photo and holiday crafting for kids. 

19. Peacock Lane

The whole family will enjoy a stroll down this famous and historic Portland street, whose homeowners deck their halls and homes from top to bottom with Christmas lights and holiday displays for the public to enjoy since the 1920s. December 15-31, 6-11 p.m.

20. Hanukkah

Celebrate the season with a grand Menorah lighting, live music, balloons, and food in Vancouver at Esther Short Park on December 2 4:30-6:30 p.m.

21. Follow the Star

Follow the Star is a 45 minute walking tour of seven outdoor live action scenes that tell the story of the search for the Christ child. Tickets are free and can be gained at the door or online by reservation. All tour groups are hosted and include 25-30 persons. Friday, Saturday, and Sunday, November 30 – December 9, 4 and 5 p.m.

22. Whale Watching Week at Depot Bay

December each year marks the gray whales migration south, along the Oregon Coast. Visit the Depot Bay Whale Watching Center, where volunteers will help you spot these gentle giants from December 27-31.

winter23. New Year’s Eve

Just because you don’t have a babysitter and you’re not partying like it’s 1999 anymore doesn’t mean that you can’t have fun out of the town with the kiddos!

  • NYE with the Portland Winterhawks vs. Seattle Thunderbirds – Join the Winterhawks for their annual New Year’s Eve game against rival, Seattle Thunderbirds starting at 7:00 p.m. In addition to the game, the party includes an inflatable bounce house and obstacle course on the concourse for kids, a cash balloon drop, and more family-friendly activities! After the game, fans will have a chance to skate with the Winterhawks players on the Moda Center ice as you countdown to midnight!
  • Skibowl’s Annual NYE Extravaganza – Want to go big and NOT be home for NYE? Skibowl puts on a massive celebration that goes all day and almost all night long! The extravaganza includes a live DJs at Skibowl West and East, Cosmic Tubing, Ski & Ride 9 p.m. until 2 a.m., and a torch light parade down the Lower Bowl that heralds two fireworks displays viewed from both east and west bowls at 12 a.m! There will also be fun winter games, multiple beer gardens, and a dance party that lasts into the night. For the kiddos there is Frosty’s Playland, a massive indoor Super Play Zone. 
  • Come back for more added soon!

24. Northwest Reptile Expo

Like things that slither? Go see the NW Reptile Expos on January 12, boasting hands-on (eek!) and interactive booths that will thrill the lizard-lover in the family. 

25. Chinese New Year Celebration

Welcome the Year of the Dog February 5-19 with a variety of family-friendly events at Lan Su Chinese Gardens. Festivities include a lion dance performance, lantern viewing, and dragon processions. 

26. Polar Plunge 5K

Even if you don’t take a plunge into the icy cold waters, it’s fun for the whole family to watch costumed crazy people jump into the freezing Columbia River on February 23 for a great cause. Brrrr!!!

27. Oregon Symphony Kids Concerts

This winter keep the late winter dreariness at bay by taking music-loving kiddos to the Oregon Symphony for their KinderConcerts and Symphony Story Times!

28. Lego Convention

Perfect for both the big and small Lego fanatics in your home, this is held at the Oregon Convention Center March 2-3!

Have any great winter activities to add? Please comment below!


  1. Beverly, girlfriend, you are a rockstar! This list is fantastic, and made planning my Thanksgiving weekend with out-of-town family so much easier! Thank you so much!

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