14 Winter Break Activities for Families

Winter break will be a shorter for many Portland families this year, due to the missed school days during the Portland Public Schools strike. Maybe you’re excited for the time off with kids. Or maybe — like some of us here at PDX Parent – you have the line, “Mom and Dad can hardly wait for school to start again,” running on repeat in your head. Either way, there’s plenty of fun to be had over break! Here are 14 ideas to get you started, one or two for each day, depending on how long your break happens to be this year.

As always, confirm all details since there may be changes at any time.

Go skating. This year you can skate outside in Portland, all break long, at the Woodsy Winter Village Downtown Pop-Up Ice Skating Rink. As in years past, you can also skate in the “snow” at the Lloyd Center or go retro at Oaks Park. There are plenty of options for getting the wiggles out on skates.

Visit the best of 2023. In the busy-ness of the year, you may have missed the Top New Kid-Friendly PDX Attractions of 2023. Winter break is the perfect time to try them out.

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. Some 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.

Find new books. Browsing the stacks at Powells is an adventure that locals and tourists alike enjoy, and BONUS, you’ll get even more quiet time at home, when the kids are lost in the latest Dog Man. Holiday budget too tight for a book splurge? Portland has fabulous libraries, where you’ll find plenty of great reads for zero dollars. If you’re looking for a new-to-you independent bookshop, we’ve got 11 ideas.

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.

Find Santa. You’ve got plenty of time before the big day to squeeze in a visit, and we’ve rounded up plenty of places to meet him. Kids think they’re too old for Santa? Hunt for this display of glowing Santas instead!

Get away. Spend a few days at one of these family-approved local destinations.

Try a new-to-you park. We highly recommend treating our 10 Best Playgrounds like a bucket list, for some free fun that will absolutely delight your kids. You’ll also find fewer crowds in winter, which means no one has to wait for a turn on the swing set. (Just maybe bring a towel to dry it off.)

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). Or attend Beaverton’s Joyous Kwanzaa Celebration on December 29. To learn more about the holiday, watch this PBS video for kids about Kwanzaa. 

See the Nutcracker. It’s not too late! Find a venue that fits your budget here, including the splurge-worthy annual performance by Oregon Ballet Theatre.

Climb, swing and slide — inside. Check out our list of indoor play spaces, including the new Dig PDX, Oregon’s largest indoor sandbox! Many have Wi-Fi, so you may even get some work done while the kids play.

Have fun in the kitchen. Try one of these easy, kid-approved holiday treats. Prefer to avoid mess in your own kitchen? Try one of these 14 places to decorate cakes and cookies with kids, instead.

Do some good. Winter break is the perfect time to volunteer at one of these 20+ kid-friendly volunteer spots.

Go on a holiday tree tour. Pack up some cocoa and see if you can check all of the community trees off your list before the lights go out.

We hope you have fun and find just the right amount of things to keep you as busy as you’d like to be. For more ideas, check out our popular Kids Calendar.