27 Portland holiday events for families: 2021 update of Christmas things to do

Happy holiday season, friends! This is such a fun time of year—but it can also be stressful for parents. You feel me, right? Between class holiday parties, looking for deals on your kids’ wish list toys, making travel plans, welcoming out-of-town guests and all the rest, you’re exhausted and looking for a strong glass of ‘nog. Let me take one item off your plate: I’ve rounded up the absolute best 2021 Portland holiday events for families so you can celebrate—without all the overwhelm.

2021 update note: The COVID-19 pandemic has changed the way we celebrate the holidays in Portland and the metro area. Some traditional Portland Christmas things to do have been modified or canceled due to the pandemic. I’ve done my best to collect the most up-to-date information about Portland Christmas events but recommend you check directly with the event organizer before attending.

Some Portland holiday events are a bust, though, and it’s such a drag to go to one and be disappointed. So read all the way through to the bottom of this post to see a few Portland holiday events to skip.

So no matter what you celebrate, there are festive ways to get in the spirit in Portland, Oregon. Bundle up the kids, put on your Raffi Christmas CD, and get ready for the best Portland holiday yet!

The jolliest must-do Portland holiday events for families

1. Portland tree lighting ceremony

Portland gathers together in Pioneer Courthouse Square, aka Portland’s Living Room, to see the lights go on all over this 75-foot-high Christmas tree. There’s also a massive caroling event. You can’t get much more festive than that! See the website for more information.

2021 update: The city of Portland has made this year’s tree lighting ceremony virtual. The event will be live-streamed online, which you can watch from home (while sipping hot cocoa, naturally). You can still stop by Pioneer Courthouse Square to see the lit-up Christmas tree on your own!

2. Christmas lights at The Grotto

Holly jolly news: Christmas at The Grotto is back!

The Grotto is a Catholic sanctuary in East Portland, and during the holidays it’s filled with gorgeous lights, live music, puppet shows and a petting zoo with a camel! We went with a group of friends last year and had a wonderful time. Bundle up, because it gets cold! Read my full review of the Christmas Lights at the Grotto.

Buy your tickets online ahead of time. Tickets are timed and specific to a given night in order to limit the number of people who visit. This year, there will be no animal petting zoo.

What’s more, you can listen to live musical performances at The Grotto. Listen to Christmas carols and other seasonal music performed by choirs and other musicians.

2021 update: The Grotto has brought back its famous annual Christmas Lights at the Grotto event after taking a year off in 2020. Visitors aged 12 and over must show proof of COVID-19 vaccination or a negative test within the last 72 hours.  

3. Hipster Santa

Sure, regular Santas are a dime a dozen this time of year. But a Hipster Santa? Now that’s uniquely Portland. He’ll be at Pioneer Square Mall on Thursdays and December 1-2, complete with his white man-bun and Naughty/Nice arm tattoos.

2021 update: The Lloyd Center, home of Hipster Santa, is back to hosting the Big Guy for photo ops! Reservations are not required this year but strongly recommended. (Make reservations, for Hipster Santa or regular Santa, here.) 

If you’re not committed to seeing Hipster Santa, other (more regular) Santas sit for photos elsewhere in Portland, too. I have been told that the Santa(s) at Frog Pond Farm is vaccinated, which I feel great about!

4. Great Figgy Pudding Caroling Competition

Dozens of vocal groups duke it out, The Voice-style, at the Great Figgy Pudding Caroling Competition in Pioneer Courthouse Square. Bring your kids to this Portland holiday event to sing along or just listen to your favorite seasonal songs. 

2021 update: The Great Figgy Pudding Caroling Competition is back in person this year! And this Portland holiday event is bigger than ever—literally. Caroling groups will sing in public spaces in a 10-block radius around Pioneer Courthouse Square. Then the top three groups will “battle” on stage at The Square on December 4, 2021 from 5:30-7:30. See the Figgy Pudding Facebook page for more info.

5. Tuba Christmas Concert

Roughly 150 tubas will play holiday favorites at this annual outdoor event at Pioneer Courthouse Square. Drop by the Tuba Christmas Concert for a song or two on December 11 from 1:30-3:30pm.

2021 update: The Portland Tuba Christmas Concert returns after a 2020 hiatus. The tuba concert will have social distancing measures in effect to reduce the risk of spreading germs.

6. Portland Zoo Lights

Most of the Oregon Zoo’s animals are asleep and staying warm during Zoo Lights, but you’ll see plenty of Christmas light displays and installations during one of our favorite Portland holiday events. We’re not the only ones who love this Portland holiday tradition: Zoo Lights is popular—and relatively busy.

Ironically, the limitations imposed because of the pandemic have made Portland Zoo Lights more mellow (and enjoyable, IMO). This also means it’s not an epic struggle to find a parking spot. Even better, take public transportation and don’t worry about parking at all!

Read my full post on going to ZooLights with kids for tips and all the details!

2021 update: This year, ZooLights is offering both a walk-through and a drive-through experience. The choice is yours! Buy tickets for timed entry to enjoy the 1.5 million lights, either on foot or from the car.

Zoo Lights runs from November 19, 2021 through January 9, 2022, excluding December 25 (Christmas). Walk-through tickets range from $16-29 and drive-through visits cost $65 per car. All admission is discounted 20% for zoo members.

7. Take a photobooth picture with a giant Christmas tree

If you go to Pioneer Courthouse Square on December 6, you can take a free photobooth picture or boomerang with the 75-foot-tall Christmas tree in the background. The photobooth is sponsored by Stumptown. See the website for more information.

2021 update: The photobooth is not currently operating.

8. Christmas lights on boats

At the annual Christmas Ships Parade, you’ll see regular boats decked out for the holidays—along with more Portlandia-type displays (like a glowing Sasquatch or waterskiing Santa!). See the event’s Facebook page for details on dates, evenings in December. In 2021, the ships float along different parts of the Columbia and Willamette Rivers between December 3 and 21, 2021.

Good news for 2021: The Christmas Ships Parade in Portland is *on*! You can safely watch ships while social distancing, so bundle up and stake out your spot to see this annual Portland Christmas tradition. Look up the schedule to choose a day to watch the Portland Christmas ships. Just remember to bundle up and maintain social distancing while you admire the parade. 

9. Ice skate around a Christmas tree

At the Lloyd Center in Portland, OR, you can skate in a rink in the middle of the mall. During the holidays, they install a tall Christmas tree so you can skate while pretending to be an elf. (If that’s your thing.)

Grown-ups can also skate around the tree to a live DJ on Fridays and Saturdays from 5:30-7:30pm. Visit the Lloyd Center skate rink site for more information.

2021 update: Ice skating is on! The Lloyd Center requires face masks for visitors, per Oregon mandates.

10. The Nutcracker

I’ve been taking my older daughter to Portland’s The Nutcracker ballet since she was 2, and we look forward to it all year! The music, the tutus, the dancing—it’s a festive way to kick off the holidays in our family, and will be for yours, too.

Level 10 travel tip: The Oregon Ballet Theater did a discount last year right after Thanksgiving, so follow their Facebook page to keep an eye on cheaper tickets.

2021 update: The Oregon Ballet Theater is once again performing The Nutcracker in-person this year! YAY! In order to attend, members of the audience ages 5 and up must show proof of vaccination or a recent negative COVID test. 

Get excited to twinkle your toes by watching the Dance of the Sugar Plum Fairy! Then check out my post with 19 top tips to see The Nutcracker with kids.

11. The Nutcracker on Ice

If you’re more into hockey than ballet, you might like seeing The Nutcracker on Ice at the Lloyd Center in Portland. December 12, 11am. Check out this page for more details.

2021 update: The Nutcracker on Ice at the Lloyd Center will be performed on one day only. Dress rehearsal will take place December 11, 2021, and you can watch the performance then, too!

12. Portland Concert-at-Christmas

Can’t decide which holiday musical performance you want to see? Treat your ears to a Christmas smorgasbord of music at the Concert-at-Christmas, performed at the Schnitz.

This concert is like a who’s who of Portland musical performing arts. You’ll see orchestras, wind ensembles and even a percussion-only performance. Each group performs a holiday-ish song or songs, including many you’ll recognize. This year the concert is on December 26 at 7:30pm.

2021 update: The Arlene Schnitzer Concert Hall requires proof of vaccination or recent negative test result for all concert-goers, including children. All members of the audience are required to wear face masks.

13. Light the night on Chanukah

Every night of Chanukah, communities gather at Pioneer Courthouse Square to light the menorah. This year, Chanukah begins on November 29 and ends December 5, 2021.

The first night of Chanukah, November 29, kicks off the holiday with a uniquely Portland flair: They’ll be carving an enormous menorah made of ice!

Bring the kids each night of Chanukah to sing songs, make crafts and of course play the dreidel! See the Facebook page of Chabad of Oregon for details.

2021 update: The menorah lighting event in Portland is back in person this year. In addition, it is live streaming virtually, so you can Zoom in.

14. Help the Cinnamon Bear save the spirit of Christmas

Toddlers and young children can help the Cinnamon Bear and the rest of this live show’s cast save the spirit of the season. Held at Oaks Park, the performance includes music and interactive elements so your toddler is welcome to shout out responses!

Tickets include a cup of hot cocoa. This Portland holiday event is stroller-friendly. See the Cinnamon Bear site for additional details.

2021 update: Last year this event was a drive-in performance. This year, it’s in person at the Oaks Park Dance Pavilion.

15. Christmas lights and miniature trains at Aspen Meadow

Throughout the grounds of Aspen Meadow south of Portland, kids will see all sorts of holiday lights displays. There are also set-ups indoors, including a miniature village and train display. Visiting the Christmas Lights at Aspen Meadow is free and they accept nonperishable food donations for the Oregon Food Bank. December 8-26; see the website for more information.

2021 update: The event at Aspen Meadow continues to be canceled this year.

16. Ride the Holiday Express with Santa

You and your kids can celebrate Christmas by riding a twinkling vintage steam engine from Oaks Park, through the woods, and back again. Santa meanders through each train car, giving children an opportunity to say hello (and maybe whisper their wish list!). 

Choose from among hourly departure times and buy tickets in advance at the Holiday Express website.

2021 update: The Holiday Express Santa train is BACK!

17. Lights and Christmas events at Victorian Belle

At this historic Portland home that’s open to the public, more than a million lights and 10 Christmas trees make this a beautiful home to tour. Live carolers, Santa and hot cider are inside, too. Admission is between $5-12, most days December 1-26, 2021; see the website for more information.

In addition, the Portland Victorian Belle is hosting other holiday events. You can make a wreath, meet Santa, create kids’ crafts and even a night of live music with a special guest appearance from Krampus himself!

2021 update: The Holiday Belle light display is open again! See the website for general admission tours of the house and holiday events.

18. Holiday displays at Pittock Mansion

Pittock Mansion, the magnificent Victorian house/museum, decorates its many extravagant rooms for the holidays. See more about these events at their website. November 22, 2021 through January 4, 2022.

You’ll want to leave time to wander the grounds in addition to exploring the mansion’s interior. On a clear day, you can see an impressive view of the Portland skyline from the grounds.

This year, the holiday theme is “Critters Make Merry.” Volunteer decorators have turned each room into a themed display.

2021 update: Pittock Mansion is once again open! You can visit the grounds and tour the mansion.

19. Go caroling on a trolley

So you like to sing but don’t love walking around in the cold? Why not carol from the inside of a vintage trolley? The 2-hour trip around Lake Oswego and South Portland on the Fa La La Trolley will help you sing loud and clear for all to hear, complete with song books and seasonal treats. Kids are welcome! December 13 and 16.

2021 update: As of the time I updated this post, the Christmas trolley has not resumed its holiday runs.

20. Eat free cookies!

Holiday cookies are the best. Holiday cookies that you don’t have to bake (or clean up after) are even better! Get a package of locally made iced cookies for free at Pioneer Courthouse Square on December 17 from 1-2pm.

2021 update: This event is currently on hold.

21. Christmas in the Garden / Silverton Christmas Market

Less than an hour south of Portland, Oregon Gardens holds an annual lights extravaganza, Christmas in the Garden. The outdoor displays use a million lights to create imaginative scenes, tunnels and more.

Christmas in the Garden, which has been renamed the Silverton Christmas Market, also includes food and drink carts, a small holiday market, a snow-less sledding hill and indoor ice skating.

2021 update: After closing to the general public in 2020, this holiday event has returned! Now operating under the name Silverton Christmas Market, the lights event will run November 26, 2021 through January 9, 2022, closed December 25 and 26. Ice skating is not available this year.

22. Portland International Raceway Winter Wonderland

Yes, it’s cold outside—but you can enjoy all the Christmas sights from the warmth of your car at Portland International Raceway’s Winter Wonderland.

The Pacific Northwest’s largest Christmas lights event showcases epic scenes and animated displays. Your car will also drive through stunning lights tunnels.

November 29, 2021 is a special bikes-only event called Bike the Lights. The following night, November 30, is open for people walking their dogs!

Entry costs $28-39 per car (online tickets only) from November 26 – December 31.

2021 update: Winter Wonderland is on! No more than six people per car and one household per car.

23. Clackamas County Winter Fair

Just a few minutes’ drive from Portland, the Clackamas County Fairgrounds have been transformed into a festive extravaganza. Christmas lights tunnels and pretty displays line a quarter-mile pathway, making this an easy distance for young’uns.

Tickets cost $15; children 11 and under get in free. Check the Winter Fair website to buy tickets and see when Santa will be onsite, too!

2021 update: The Clackamas County Winter Fair holiday display is now open for walk-through visits.

24. Christmas Fantasy Trail

Feel like you’re walking through a fairy tail at the Christmas Fantasy Trail at Wenzel Farm. This annual, outdoor event includes a wooded trail brightened with Christmas lights.

Admire adorable cottages and walk across a mini-suspension bridge, too. This Oregon City holiday event isn’t fancy but is charming. Kids in particular love it!

2021 update: The Christmas Fantasy Trail is still canceled.

25. Christmas lights trail at Maddax Woods

Just a short drive from Portland, this holiday event is fun for families—including the dogs! Maddax Woods in West Linn is decorated every year with Christmas lights, including displays of native animals like owls and raccoons. 

This short, wooded trail has only a small parking lot so be prepared to park in the residential neighborhood and walk to the trailhead. It starts out with a short, steep hill but is an easy walk otherwise.

2021 update: As of the day I updated this post, I couldn’t find details about the 2021 plans for Maddax Woods. Considering this is an outside event, I am betting it will take place. Make sure you wear a mask and practice social distancing at this Portland-area Christmas event. 

26. Drive-through community events

COVID-19 can’t dampen our holiday spirits! In response to the many closures and cancelations this holiday, some communities are organizing drive-through events.

(We’ll be going to West Linn’s Candy Cane Lane drive-through this year.)

Simply search your neighborhood and “holiday drive through” to find one near you.

27. Help those less fortunate

Whether you volunteer at a soup kitchen, sing at a retirement community or fill a stocking for the homeless, one of the best ways you can celebrate the holidays is to give back. Make helping others a part of your holiday tradition this year.

Every year we buy gifts for a teen who is in the foster care system, through Project 48. Consider how you can make someone else’s holiday happier in a way that feels meaningful to you.

The Portland holiday events to skip

Not all Portland holiday events are created equal. Here are several I don’t recommend.

Reindeer at 7dees

You’ll never see more depressing reindeer, I guarantee it. They’re kept in a small pen on concrete, and they look so sad. This kind of animal display will not bring you holiday cheer.

Christmas lights at Peacock Lane

I may catch flack for this, but I wouldn’t recommend driving Portland’s Peacock Lane to see the Christmas lights there. It is so trafficked that it becomes a madhouse. The exception: Peacock Lane is closed to cars and open only to pedestrians December 15-17, so carpool or take public transportation!

2021 update: After taking a year off due to COVID-19, residents of Peacock Lane reinstated this Portland Christmas event this year.

How will you be celebrating the holidays? Do you have your eye on any 2021 Portland holiday events?

Want more family activities to do in Portland? See my posts on the Chinese Garden and the Japanese Garden, both kid-friendly destinations in Portland.