2022 of Portland's

Weirdest Holiday Events in 2022

We love the weirdness of the Rose City, and the holidays are certainly a time when the weirdest of weird shine. There's plenty of events and locations that will make you say, "Yeah, we get why they say this place is strange," along with tons of Christmassy tradition and cheer, too. And a couple of nonreligious/Pagan/Jewish events too! And listen, they're numbered, but they're in no order. They're all our favorite things! Before you get your holiday festivities on, make sure you...

GET YOUR ROOM (or book a room for the in-laws... whatever you need this holiday season!)

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22. Hipster Santa

You probably never thought you'd hear "Man Bun" and "Santa" in the same sentence, but here we are... in Portland. Home of the "hipster" has to come with a bespectacled, tattooed, sweater-weather-lover like the Hipster Santa of yore. Take photos with Santa atop his Buffalo-plaid-checked knee on the biggest chair made from PDX's now-ancient airport carpet design. It literally doesn't get more hipster than this. Reservations are not required, but they are encouraged at the pioneerplace.com website.

21. Peacock Lane

Each house in this quaint southeast neighborhood has been decorating for Christmas for decades. Mostly Tudors, the houses are adorned with not only beautiful sparkling lights but also nativity scenes, rotating Christmas trees and stunningly life-like replicas of Santa and Frosty. Come see the lights on Peacock Lane and you’ll find nothing but good, old-fashioned holiday spirit. Sometimes the kids sell hot cocoa, but be ready with your own so you don't get too chilly out there!

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20. Public Menorah Lighting

Chabad of Oregon will have the honor of lighting the giant menorah in Pioneer Courthouse Square; a ceremony bolstered by live music, Hanukkah noshes, "dignitaries," and other family-friendly festivities. Roll up to Pioneer Square every night of Hanukkah between 5:30pm-6:00pm to be a part of the magic!

19. Crafty Wonderland

With over 200 vendors, and what feels like MILES of local artisans slinging their holiday wares, you'll find whatever kind of gifts you're looking for. Kitschy ornaments with real taxidermy inside? It's there. Delightfully sarcastic cards and notes for any holiday needs? They've got it. Hand-crafted goods of all shapes and sizes? Of course... it's Portland! With a pre-ticketed Friday opening and general admission Saturday and Sunday, the Oregon Convention Center (just a short walk from the hotel) will be filled with the best of Portland's makers for this giant holiday market.
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18. Krampus Photo Sesh

Aw dang, we just heard that this year's 2022 session is cancelled. Bummer! But they will definitely be back in 2023. If you're not a fan of the traditional Santa photos, but your in-laws are begging for shots with you and the fam, look no further than the bad boy of Christmas... Krampus! Sit in this dude's lap while you fight the urge to describe every good deed you've done in an effort not to get on his bad side... and tell the kids to be extra good this year... or else! 

17. ZooLights & Brew Lights

Oregon Zoo opens up their gates (only the front ones... not the ones with, you know, the animals) to late night zoo-goers during the holiday season for epic Christmas light viewing at ZooLights! Plus, it's a chance to get down and dirty with the animals you don't usually get to see during the day. Find a few nocturnal friends (like, actual people, not just the bats and bears), and jump on the train that rides around the zoo to see the light spectacular! Over 21? Head to the boozy version: BrewLights!
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16. Tuba Christmas

Portland's living room (aka Pioneer Square) will be filled with the big brass sounds of 150 tubas as they play Christmas tunes in unison during this free, annual holiday tradition. DO NOT be ashamed to bring earplugs, as this event gets BIG sound going, as you might have guessed because of the ONE HUNDRED AND  FIFTY tubas in attendance. But it's cool. Big Home Alone polka band energy, in the best way possible.

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15. Holiday Ale Festival

Uncork a beer-inspired carol of your own during downtown Portland’s annual Holiday Ale Festival. This annual celebration of winter suds is set beneath the region’s largest decorated Christmas tree. Revelers can sample from more than 50 featured beers, each designed to keep drinkers warm on cold winter nights. The Holiday Ale Festival also includes delicious, holiday-themed foods, live music and a Sunday brunch with exclusive beers. Tickets are required... so is a solid DD you can count on!

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14. Winter Wonderland at Portland International Raceway

Recognized throughout the PNW as the “Largest Holiday Light Show West of the Mississippi”, Winter Wonderland will grab your attention with glimmers and glows around every corner. Enjoy the most spectacular drive-through light show in the region from the comfort of their own vehicles, viewing over 250 colorful light set pieces and many fully animated scenes along the way.

13. Festivus at Hey Love

Hey Love throws a Festivus celebration, featuring a one-night-only menu with Jewish-inspired Chinese food offerings, like Roast Duck Matzo Ball Soup and Nathan's Kosher Frank Egg Rolls, plus "Mazel Tov cocktails" to sip on throughout the evening. No reservations are required and the event is all ages until 9 pm when DJs take control of the tables for the 21+ crowd.

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12. Tree Lighting at Pioneer Square

Portland’s Tree Lighting will be live & in-person at Pioneer Square the day after Thanksgiving, Fri, Nov 25th. Featuring a joyful sing-along with Portland’s own Thomas Lauderdale from Pink Martini, local musicians and chorale singers, this event is the highlight of the holiday season downtown.  Join in the celebration as Santa Claus flips the switch to illuminate more than 14,000 colorful LED lights on our City’s 75 ft Douglas-fir. The Square fills up, so get there early, and consider taking the MAX over to avoid parking!

11. Holiday Movie Nights at Jupiter Original & NEXT

Want to get out of the house for the weekend? The Burnside hotel Jupiter is hosting a holiday staycation experience that includes DVD players, holiday movies from Movie Madness, including the Festivus episode of Seinfeld, and all the essential festive snacks and drinks your heart desires (plus a hotel room to enjoy such activities in, of course).

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10. Paddle Boarding Santas

Have an ugly sweater that's grown into an entire ugly Christmas sweater outfit? Check out this wildly Portland event that has been a charity event, asking attendees to bring a toy gift for kids for the holiday season. Depending on the weather, the SUP trip might be as far as the Sellwood Bridge to downtown, or you might just have to grin and bear it while wearing your tinsel-laden best in freezing rain. It's winter in Portland!

9. Christmas Festival of Lights at the Grotto

Calling all die-hard Christmas fans (and maybe the Die Hard as a Christmas movie fans, too, but that's beside the point)... Get your fill of religiously delightful Christmas traditions. You'll get caroling, nativity scenes, gorgeously decorated church chapels, and so much festive joy, you won't want to leave. Plus, you'll get tons of lights, story time and puppet shows for kids, and more!
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8. Holiday Express Train at Oregon Rail Heritage Center

Be transported along the Willamette River in the heart of the city in vintage rail cars all pulled by the historic Polson #2 1912 steam locomotive. Join Santa Claus and his elves for a magical ride that starts at the Oregon Rail Heritage Center. Is it corny? Yeah, of course, but it's also super kid-friendly and a great way to bring the Christmas spirit back to your cold, Scrooge-like heart.

7. Holiday Horror Movies

Who says the holidays have to be all about family? Why not add a little gore to that holiday lore with a selection of devilishly divine holiday frights like ThanksKilling, Gremlins, Krampus and many more. Hit up our pals at Movie Madness this holiday season and pick up your favorite Holiday Horror Films for your own movie marathon, especially if Santa Claus costumes make you a little… nervous, and you think poinsettias look best in blood red.

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6. Singing Christmas Tree

Because what better way to celebrate the season than by having and absolute TON of choir singers belting Christmas tunes while being stacked in the shape of a Christmas tree? From the cinematic living nativity and a visit from Santa and his dancing elves, you’ll experience non-stop music, dance & pageantry that will kick off your Holiday Season. New show, new songs, same Christmas story.

5. Ice Skating at Lloyd Center

Y'all might not know this, but Lloyd Center's ice rink was the nation's first ice rink located inside a shopping center upon the mall's opening. While they're open all year long, the holidays are the most fun. Why? They put a dolled up Xmas tree right in the center of the rink! To us, that means just another thing to try to avoid as we blindly meander around on rented skates while trying not to accidentally clothesline any nearby kids, but to each their own!
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4. SantaCon

Picture this: You're picking up a little something from Old Town Pizza, and Oops! You nearly run into a fairly robust young gentleman wearing a Santa costume. You lift a hand to wave, looking up, and realize that there are THOUSANDS of people dressed as Santa and his little elf minions... Welcome! You've just walked into the charity-fundraising drinking extravaganza, SantaCon! Get your holiday cheer on by dressing up as the big man in red, along with about 2500 others, and get partying!

3. Daimler Half Marathon

Get in the holiday spirit and bookend your race season with Portland’s favorite winter Half Marathon, 10 miler, 10K, 5K, Virtual options and our multi-day distance challenges this December! All races now start and finish on Swan Island and feature carolers and cookies along the course! Plus, there are ugly sweater long-sleeve tech shirts and medals, carolers, cookie stations, DJs, and an epic costume competition. Who doesn't want to run 13.1 miles while wearing pointy elf shoes?! Run!!!

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2. Christmas Ships

The Christmas Ship Parade started in 1954 with one lone sailboat from Portland Yacht Club. Bows of green with some ribbon where tied along the rails and it paraded on the rivers. The next year the parade started to grow. Today, The Christmas Ship Fleet averages about 55 to 60 boats between the Columbia and Willamette River fleets. Things have changed from the first lone ship. Now the displays are brightly lit and can be seen from bank to bank on each river.

1. U-Cut Christmas Tree Farm

Your perfect holiday conifer quest comes with a hayride/reindeer/artificial snow/chili cheese nachos? We got you. Check out this list of nearby (within 90 miles) U-Cut Christmas Tree Farms where you can get your perfect conifer ready for the most festive time of the year. Tinsel not included, but there could be a petting zoo involved!

MAKE A NIGHT OF IT AT JUPITER

Get your holiday on hard, then unwind in the center of it all! Need a place to cozy up and decompress before heading up to your room for the evening? Stop in at Hey Love or Doug Fir Lounge for a night cap. Winter at Jupiter Hotel is unparalleled. All we need is YOU.

GET YOUR ROOM

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