Winter break seemed a little long in the best of times when there was (in retrospect) plenty to do. But despite the pandemic, the closures and the weather, there’s still fun to be had for families in the Portland area. Here are some ways to have the best winter break ever possible in 2020.

If you head out: Confirm all details since there may be changes at any time, and follow social-distancing best practices. 

Play in the snow. It may or may not snow in Portland, but you can check out the sledding, snowshoeing and skiing at these family-friendly spots. PDX Parent staffers are planning to go to Mt. Hood Skibowl or the sno-parks around Mt. Hood. Another farther-out favorite is Wanago Sno Park in Bend.


Catch NWCT’s holiday show. Seeing the holiday show at Northwest Children’s Theater is a family tradition for us, and this year, it’s going virtual. In Home for the Holidays, Perry Winkle, the puppet star of How Do You Do?, along with NWCT artists and staff, celebrates the magic of theater and relives on-stage moments from your favorite NWCT holiday shows — like Matilda, Mary Poppins, Cinderella and The Wizard of Oz. It’s free to watch although donations to NWCT are encouraged to support their online programming during the pandemic.

Go roller skating — in the Lloyd Center parking garage. Here’s something you would never have imagined last year: Rose City Rollers are hosting skate sessions in the covered, open-air third floor of the Lloyd Center parking garage. You can rent gear there or bring your own. Tickets required.

Get a bookstore all to yourself. If you don’t feel comfortable bringing the whole family to browse for books, you can make a private appointment at Backstory Book and Yarn. Our editor and her family spent a glorious hour there and left with a bag of used books to keep the kids (and grown-ups!) engaged.

Be dazzled. Most holiday light displays are running through January 1. Check our list here to find old favorites or new sparkling spots. Don’t forget another great source of inexpensive and easy bright holiday cheer is your own neighborhood, or you can pick a new neighborhood to explore on foot or by car. Have you found the display of glowing, masked Santas hiding in Portland?

Get away to the coast. Our guest columnist loves Cannon Beach in the off-season.


Try a new-to-you park. These days my family and I are going to a lot of nature parks, and it makes it more interesting and fun for us to have new places to explore. Check this list of parks recommended by PP&R for winter explorations, or venture farther out with one of these Metro parks for families. And if kids love visiting their old favorites, that’s a win, too. (Anything’s a win.)

Learn about Kwanzaa. The African-American celebration of life and family begins December 26 and ends January 1. You can decorate your home with the colors red, black and green, and reflect on each of the seven guiding principles (unity, self-determination, collective work and responsibility, cooperative economics, purpose, creativity and faith). Help the kids craft colorful paper garlands, woven placemats and beaded necklaces. To learn more about the holiday, watch this PBS video for kids about Kwanzaa. 

See the Cinnamon Bear Holiday Show at Oaks Park. This live, drive-in show features musical performances of holiday favorites sprinkled into a storytelling adventure. The audience helps Cinnamon Bear (and, yes, Santa is there, too) to locate a stolen magic star and restore the needed holiday spirit. You can order snacks and hot chocolate delivered right to your car! Get the details here, or read our review and tips

Climb, swing and slide. Playgrounds are open! My daughter recently had a fantastic time at Spring Garden Park and I realized that she had really been missing time on the playground. Bring hand sanitizer and a towel in case equipment is wet, and be prepared to leave and come back a different day if it’s crowded or you don’t feel it’s safe. Here are some of our all-time favorite playgrounds and a list of play spaces with lovely views.

Have fun in the kitchen. Try one of these easy, kid-approved holiday treats. You can always find more ideas in our online Recipe Files

Make a winter wonderland in a jar. Everyone loves a snow globe. Learn how to make one with the kids and sneak in a science lesson, too. 

Beautify the neighborhood. Local nonprofit Adopt One Block has a simple, grassroots approach to improve your neighborhood. When you sign up to be a block ambassador, you commit to cleaning up the block of your choice on your own schedule with supplies they deliver to you for free. Over 400 blocks have been adopted so far.

Dream about the future. This idea comes from our recent article of pediatricians’ tips to help kids overcome stress and find joy. Plan a family vacation together, and research spots you’d like to visit someday, or create your bucket list for 2021.

Michelle Carew
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