Everything You Need to Do in Portland This Holiday Season

Are you preparing to dust off that SAD lamp and max out your credit card on an overpriced flight back to wherever it is your parents live because winter is here? Hold it right there, friend! It’s true that endless rain is a tad less festive than the snow other areas get, but to be fair, Portland doesn’t mess around when it comes to rolling out the holiday spirit. Between beer festivals, witch-themed winter balls, and the annual appearance of our very own Hipster Santa, this holiday season is certain to remind you why it is you moved here and made it so annoying to go home for the holidays in the first place (aside from your odd uncle Lloyd). Winter Portland is the best, and this docket of tasty holiday events is here prove it.

Portland Festival of Lights
Portland Festival of Lights | Victoria Ditkovsky/Shutterstock.com

Get your photo taken with Hipster Santa

Man bun? Check. Authentic Pendleton Big Lebowski sweater? Check. Throne decked out with the PDX airport carpet pattern? Duh. This is Portland, and we take hipsterism very seriously here, which is why Pioneer Place employs a guy who looks like a lifelong Stumptown barista to play Santa every Thursday until mid-December.
Cost: Free; reservations are encouraged, but not required

Go Downtown to watch Portland hit the 'on' switch on a massive Christmas tree

Gather ‘round and feast your eyes on thousands of LED bulbs as they flicker to life in “Portland’s living room” while various food carts and vendors supplement the face-melting festival of lights.
Cost: Free, but bring cash for the array of food carts

Get extremely lit at the zoo

Marvel at the Oregon Zoo all decked out in millions of LED lights while the animals are away for the winter. It’s bright and shiny family fun... that’s much less smelly to boot.
Cost: $9.95 for kids 3-11, $12.95 for seniors 65+, $14.95 for adults

Sing the song of Oh Christmas Ale, Oh Christmas Ale!

Revel in an extended weekend of malty, spicy ales under a gigantic Christmas tree at the Holiday Ale Festival. It’s that one time of year when drinking beer all gussied up with fig, clove, cinnamon, and a variety of other ingredients made popular by Bath and Body Works is acceptable. So definitely enjoy it while you can.
Cost: $35 for general admission, $100 for VIP

Hate Thanksgiving weekend? Wine about it!

Leave it to Oregon’s Willamette Valley -- an idyllic expanse of vineyards and family estates about 30 miles southwest of Portland proper -- to offer something fermented and fruity for all tastes and budgets. A designated driver is a must, so conscript your kinda weird uncle Lloyd into driving everyone down there for the weekend to argue about sports and politics in someone else’s yard for a change.
Cost: It’s free to drive around Yamhill County, but we recommend buying a sober friend lunch in exchange for a ride

Watch a Christmas tree made of humans sing seasonal classics

No, this isn’t the umpteenth deviation from the Human Centipede franchise -- just a jolly old evening of holiday classics sung by dancing Santas and an adult glee choir that just so happens to be arranged like a giant Christmas tree.
Cost: $20-$60

Deck your dang halls!

Still decorating your digs with discounted post-season purchases from TJ Maxx and Ross? Step your game up. There’s dignity in doing it right, and the easiest way to snag some proper trimmings for your home is at the Christmas Bazaar, an epic one-stop holiday shopping experience at the Portland Expo Center. Show up for the tinsel; leave with a keg of nog. It’s a win-win.
Cost: $8 for adults, $3 for children 12-17, free for children under 12

Take the train to Christmas Town

You now have an excuse to drive the family an hour east to board a train that transports travelers from the Columbia River Gorge’s foremost drinking town, through the winter wonderland of Mount Hood’s northern slope, and up to Parkdale. It’s the closest thing we’ll ever get to a Polar Express experience, only this one involves craft breweries at both ends of the journey if you so choose to include them. On second thought, maybe leave the kids behind.
Cost: $37-$65 for children 2-12, $47-85 for adults, depending on cabin selection

See the light(s) at the Grotto

Though it’s technically a Catholic sanctuary that famously disallowed Portland Public Schools choirs from singing secular holiday songs during its annual Christmas Festival of Lights, it’s still a magical experience regardless of your religious affiliation or lack thereof. Just pretend you’re at a wedding and ignore the proceedings like you always do, right?
Cost: $6 for children 3-12, $10 for seniors 65+ and military, $11 for adults

Travel south for Christmas in the Garden

Head down to the Oregon Garden in Silverton for ice skating, artisanal holiday goods, Christmas karaoke and enough mulled wine and beer from Salem’s Gilgamesh Brewing to make it fun.
Cost: $3-$45 depending on activities

Experience artisanal Etsy chic in real life

Now’s your chance to actually try on that $50 enamel avocado-shaped pendant necklace in real life instead of hoping it looks in person as it did online, and it’s all for a good cause (10% of proceeds go to the Center of Developmental Health).
Cost: Free

Enjoy a ‘White Album’ Christmas

It’s shocking Cirque du Soleil didn’t think of adapting the Beatles’ eponymous 1968 masterpiece into a Christmas extravaganza featuring jugglers, aerialists, and bespoke clowns prior to a local circus troupe, so you better go see it in a small-ish theater for less than $100 a ticket while you still can.
Cost: $32.50-$50
Wonder Ballroom
Wonder Ballroom | Flickr/Nathan Forsheim

Get lost in the trees at the Convention Center

Here’s a prime opportunity for those of us bound to 200-square-foot studios and stricken with seasonal foliage-induced FOMO to marvel at the Christmas trees of folks with much more time and money than we’ll ever have.
Cost: $8 for children 3-12, $9 for seniors 65+, $10 for adults

Go walking... er, driving in a winter wonderland

Ever wanted to take your tricked out Jetta on the Portland International Raceway and experience the thrill of watching chumps eat your dust? Well, this is not that occasion, but it is a chance to slow-roll through the track and watch some pretty cool holiday lights whizz by at about 10 mph.
Cost: $18-$50 depending on vehicle capacity

Dress like Santa and go on a MAX-based bar crawl

It’s unclear how NoPDXAnticon is an actual alternative to SantaCon... especially when it sounds dubiously similar to the cheeky and boozy yearly event. But organizers are encouraging participants to donate toys to nearby dive Kenton Station’s annual holiday toy drive, so there’s something to feel good about besides the obvious belly full of booze.
Cost: Free, but you should donate a canned good and pay for your MAX ticket like the upstanding citizen you are

Sip on some cider at EastBurn

Gluten intolerance is a cruel mistress year-round, but it’s especially unfair throughout the holidays when all those malty winter beers are off limits. Thank EastBurn for putting forth the effort to include the hop adverse and gluten intolerant in their seasonal processions, which hopes to shake up some holiday cheer for Toys for Tots.
Cost: $10

Assemble your coven for a witchy winter evening

With a docket consisting of synth pop and various aerial and dark circus performances, Vespertine Winter Ball is essentially Festivus for goth kids who have just one day of the year when donning all white is actually encouraged.
Cost: $40 advance, $45 day of

Get crafty with your Christmas shopping

In the market for the twee-est of twee Portland- and PNW-made gifts for friends and loved ones this year? Crafty Wonderland Holiday Market has you totally covered.
Cost: Free

Put on your red velvet dance pants

Not quite as epic as it’s infamous NY-based brethren, Portland’s SantaCon is still one hell of a fine excuse to throw on a Santa suit, get tipsy and dance your weekend away at a handful of Pearl District and Old Town bars and clubs.
Cost: $10 (but bring more money for drinks)

Ring in the new year with homegrown electro-pop

OK, so STRFKR technically bid Portland adieu a few years ago after their most obnoxiously unforgettable song was placed in a Target commercial, and their quirky electro-pop became the default setting for coffee shop Pandora stations across the nation, but we still love ‘em enough to marvel at their delightfully gaudy neon-glazed live show for two straight nights.
Cost: $30 advance, $35 day of

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Pete Cottell is a freelance journalist/barista who may or may not be living in a van in front of your house in Southeast Portland. Follow his adVANtures at @Vanifestdestiny.