Downtown holiday events

The heart of Portland brims with holiday cheer and activities starting in November.

hipstersanta5Santa dons his iconic hipster threads on Thursdays at the Square.

Portland is unlike anywhere else in the world, so it makes sense that holidays here have their own twist. From Hipster Santa to one-of-a-kind shopping, downtown Portland offers experiences you can’t get at big box stores or online. Bonus: It’s even easier to enjoy a uniquely Portland holiday when you park for free at SmartPark garages all day on Sunday, Dec. 3, 10 and 17. Just validate your ticket (up to $5) at the PDX Pop-Up Shops in Pioneer Place or Boys Fort at Southwest Ninth Avenue and Morrison Street.

Looking for the best of what downtown Portland has to offer this holiday? These highlights will keep you merry and bright all season long.

Events at Pioneer Courthouse Square

Nov. 9–Dec. 9, 2017

Your living room is the spot for most of your family’s holiday traditions. It makes sense why Pioneer Courthouse Square — aka Portland’s Living Room — is hosting a whole slew of festive (and free!) entertainment. Family-friendly activities include the annual Tree Lighting Ceremony, the Great Figgy Pudding Caroling Competition, the annual Tuba Christmas Concert and community performances. See the entire listing, including dates and times, at TheSquarePDX.org.

Meet Santa at Pioneer Place

Nov. 16–Dec. 24, 2017

The big guy himself is stationed at Pioneer Place seven days a week, beginning Nov. 16. Kids can bring their Christmas lists and biggest smiles for the photo opportunity. Furry family members can also share their wish lists on Monday evenings from Nov. 20–Dec. 18, when Santa welcomes pets. The now famous Hipster Santa sets up shop on Thursdays at Pioneer Place.

PDX Pop-Up Shops

Nov. 16–Dec. 24, 2017

The eighth annual PDX Pop-Up Shops host local makers in vacant shop space downtown. From Nov. 16–Dec. 24, 2017, independent designers and artisans set up shop in Pioneer Place mall and the Standard Insurance Center. There, shoppers can find everything from organic handmade soaps and cashmere clothing, to statement jewelry and t-shirts designed by at-risk youth.

Little Boxes

Nov. 24–26, 2017

The three-day shopping event Little Boxes celebrates the specialty retailers that help make Portland a holiday wonderland. For the days following Thanksgiving, head to participating small businesses to earn raffle tickets and unlock prizes. In case the chance to win gift certificates and even a destination vacation isn’t enough, shoppers can score additional goodies. These include snacks, free gift wrapping supplies and a $5 SmartPark validation at the Umpqua Bank in Fox Tower on Nov. 24 and 25 from noon–4 p.m. Download the Little Boxes app to find participating businesses and plan your shopping route.

Holiday Ale Festival

Nov. 29–Dec. 3, 2017

You can drink for a good cause (and to your good cheer) at the 22nd annual Holiday Ale Festival, held at Pioneer Courthouse Square from Nov. 29–Dec. 3. For added holiday spirit, this year’s festival raises funds for the Children’s Cancer Association. The festival’s 50 hearty ales will keep you warm (and give you a little liquid courage to brave the holiday crowds). Sip your way through all 50 while admiring the square’s decorated tree (the largest in the region).

Menorah lighting

Dec. 12–19, 2017

Celebrate every night of Chanukah with the whole community at nightly menorah lightings in Director Park, hosted by Chabad of Oregon. The first night of the Festival of Lights is Dec. 12, beginning with music, traditional foods, children’s crafts and local dignitaries lighting the holiday’s first candles.

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