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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 at Skibowl 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! Open now!

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:

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 a belly 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 through December 22.

5. Pittock Mansion’s Symbols of the Season

This historical Portland home turned museum decks it’s halls every holiday season. This year the decorations are inspired by symbols of the holiday season from angels to Santa and snowflakes to candy canes.  November 21-December 31.

6. Macy’s Holiday Parade

Who needs Black Friday shopping? Instead, pack up the family and head downtown Portland for the annual Macy’s Holiday Parade on Friday, November 25. Featuring over 25 floats, local marching bands, costumed characters and, of course, Santa and his sleigh!


7. Tree Lighting at the Pioneer Courthouse Square

Get into the spirit and kick off the holiday season with the lighting Portland’s 75-foot Douglas Fir tree on November 25. Festivities get started at 5:30 but get there early to secure a prime viewing spot! 

8. Local Tree Lighting Ceremonies

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

9. 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! November 25 – January 1.  

10. 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. November 25 – January 1.

11. 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 November 26 – December 27. 

winter12. 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 25 – December 25. 

13. 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 November 25!

  • 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.

14. Dickens Carolers at McMenamins

Enjoy the sounds of the season from the Dickens Carolers throughout the month of December while they stroll the grounds at these historic McMenamin’s properties: Cornelius Pass Roadhouse, Edgefield, Grand Lodge, and Hotel Oregon.

15. 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. December 2-18. 

16. Take in a Show

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

17. 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, benefiting the Union League of Portland. The best part is no clean up required! Choose from three, separate decorating sessions on December 3.

18. Jingle Bell Run/Walk

Get out in the fresh air for a festive run/walk in downtown Portland on December 4. Ugly sweaters encouraged!

19. Ariel Tram Winter Holiday Event

Take in the panoramic views from the Portland Ariel Tram on December 10, starting at 12 p.m. Activities include family photo and holiday crafting for kids. 

20. Peacock Lanewinter

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.

21. Jewish Holiday Culinary Experience

This innovative cooking program for adults and children ages 5-12 features a family bonding experience on December 18 preparing delicious recipes, and discussing the Chag. Preregistration required.

22. Menorah Lighting at Director Park

Celebrate the first night of Hanukkah with the lighting of the giant menorah at sundown, starting on December 24 at Direct Park.

23. 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.

winter24. 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!

  • Toyota NYE with the Portland Winterhawks vs. Seattle Thunderbirds – Join the Winterhawks for the annual New Year’s Eve game against rival Thunderbirds starting at 7:30 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!
  • Oak’s Park “Rink in the New Year” – From 7 p.m. – 1 a.m. your family can roll into 2017 with games, raffles, and, of course, roller skating!
  • Out of This World Pizza NYE Bash – For the younger set, Out of This World Pizza in Hillsboro is the perfect place to let the kids run wild for the last hours of 2016 while the parents enjoy a pizza and salad buffet and beer! Put the kids down for late naps that day since the NYE party goes from 9 p.m. – 12:30 a.m. Reservations required.
  • Skibowl’s 29th 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 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. 

25. Northwest Reptile Expo

Like things that slither? Go see the NW Reptile Expos on January 14, boasting hands-on (eek!) and interactive booths that will thrill the lizard-lover in the family.

26. Great Train Expo

Got a locomotive fan in the family? The Great Train Show January 16-17 is a traveling train show that features operating model railroads, hands-on exhibits, demonstrations, workshops, and much more. 

27. Chinese New Year Celebration

Welcome the Year of the Rooster January 28 – February 12 with a variety of family-friendly events at Lan Su Chinese Gardens. Festivities include a lion dance performance, lantern viewing, and dragon processions. 

28. 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 25 for a great cause. Brrrr!!!

29. Oregon Symphony Kids Concerts

In February and March keep the late winter dreariness at bay by taking music-loving kiddos to the Oregon Symphony showings of The Pied Piper of Portlandia and Castles and Wizards.

30. Lego Convention

Perfect for both the big and small Lego fanatics in your home, this is held at the Oregon Convention Center March 11-12!

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


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3 Responses to The Ultimate Portland Winter Bucket List

  1. Amanda
    Amanda November 23, 2015 at 9:54 am #

    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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