Downtown holiday events

Downtown Portland becomes a winter wonderland with unique shopping, events, food and fun.

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

The timeless carol may insist there are 12 days of Christmas, but let’s not be grinchy about the holidays: When it comes to seasonal shenanigans in downtown Portland, the more, the merrier!

So leave the holidays-as-usual to some other town. When you’re in PDX, here’s how to do the holidays right.

Holiday events with a PDX twist

This city keeps Portland holidays weird, and Pioneer Courthouse Square is at the center of the free festivities. Don’t miss:

  • The city’s largest sing-along, led by Pink Martini’s Thomas Lauderdale, during the Tree Lighting Ceremony on Nov. 23. (Listen for his ad-libbed lyrics!)
  • Roughly 300 tubas (and euphoniums!) playing holiday favorites in unison on Dec. 8.
  • A caroling throw-down, aka The Great Figgy Pudding Caroling Competition, is on Dec. 7. Winners get North Pole bragging rights and a $1,000 grand prize

More — including a cookie giveaway and al fresco dance performances — can be found at TheSquarePDX.org.

#OnlyInPortland shopping

Whether you’re hosting the holidays or out-of-towners are staying put (big sigh of relief), gift them a taste of what makes Portland unique.

PDX Pop-Up Shops are back, turning unused retail space into a launchpad for up-and-coming brands. BlackSheepMade’s cozy, hand-knit accessories and wall hangings will keep loved ones cozy for the winter; Cloth & Ore includes jewelry, boho luxe apparel and handwoven home textiles from three local designers; and City Pop features handcrafted trinkets and original art by female artists in PDX.

If you’re looking for something new, 35 retail stores and restaurants have opened in downtown Portland this year. Shoppers are already buzzing about MUJI’s latest U.S. storefront in the historic Meier & Frank building, which is its only location in the Pacific Northwest. And ZARA recently added a two-story space in Pioneer Place, selling gifts for the ladies, gents and kids on your list.

While you’re at Pioneer Place, share your own wish list with the Big Guy himself: Santa will be posing for pics ready for the ‘Gram through Dec. 24. And Hipster Santa (with his man bun and Naughty/Nice tattoos, of course) is on hand Thursdays and Dec. 1 and 2.

Fuel up

Even Santa needs to stay hydrated and nourished during the holidays. Take a tip from him and fill up to stay jolly. Some of our favorite spots to eat, drink and be merry in downtown Portland include:

  • Blue Star Donuts: This Insta-famous bakery’s new flagship space triples the size of its original location, which means more room to sample a doughnut (or a dozen).
  • Tea Bar: This Portland standby adds a location near Nordstrom so you can caffeinate before braving the crowds. (And yes, they serve a pumpkin spice tea latte.)
  • Il Solito: Need something that’ll stick to your ribs? Stop in for handmade pasta, meatballs, a chicken parm sandwich or an exquisitely crafted cocktail.
  • Bistro Agnes: This new Parisian bistro eatery by James Beard Award-winning chefs will add a bit of French sophistication to your fête-ing.

Save cents — park for free!

It may be better to give than receive, but you’re not about to turn down free money. So when you head to downtown Portland on Sundays, December 2, 9, 16 and 23, visit the PDX Pop-Up Shop in Pioneer Place or Boys Fort to get a $5 SmartPark voucher you can redeem at nearby garages. Whether you use the cash to tip your barista, donate to the bell-ringing Santas or buy yourself an extra bottle of ‘nog is completely up to you.

No matter how you celebrate the holidays, the season is more special with a sprinkle of downtown Portland flair!

For more information on downtown events and happenings this season, visit downtownportland.org and follow us on Facebook, Twitter and Instagram.


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