Downtown holiday events

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

macysSanta makes a surprise appearance at the Macy's Thanksgiving Day Parade.
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    Willamette Week

    When it comes to holiday cheer, there’s no better place to revel than in downtown Portland, where dozens of new events and annual favorites will arrive this holiday season.

    Festive events

    The holiday season in Portland gets an early start with the arrival of the gigantic Stimson Lumber Tree in “Portland’s Living Room” on Nov. 10. The following day, Pioneer Courthouse Square’s iconic “Umbrella Man” (formally titled “Allow Me”) will be dressed in his most festive ugly knitted sweater. Join in on the fun by coming downtown and taking selfies with him and other “yarn-bombed” statues. (Tag your pictures with #uglysweaterpdx for a chance to have your photo featured on @downtownPDX’s Instagram.)

    Jingle all the way downtown the Friday after Thanksgiving, Nov. 25, for the annual Macy’s Holiday Parade. Starting at 9 a.m., the parade features floats, local high school marching bands, and more than 600 costumed characters winding their way through downtown Portland and concluding with a visit by Santa himself. Stick around that afternoon for the Annual Tree Lighting Ceremony at 5:30 p.m., which will include a joyful community sing-a-long of holiday songs. Get even more cheerful at the Holiday Ale Festival, a five-day beer tasting event at the Square Nov. 30-Dec. 4.

    Celebrate beer at the Holiday Ale Festival.

    Celebrate beer at the Holiday Ale Festival.

    Other events include Portland’s Saturday Market’s Artisan Festival, which will feature unique, locally-made gifts including woodworking, art, jewelry and handbags Dec. 6-9. The Great Figgy Pudding Caroling Competition, presented by Portland Mall Management, Inc., is a fun and festive event that will bring caroling groups of all ages to the heart of downtown Dec. 9 from 5:30-7:30 p.m. Prizes will be awarded to the top caroling groups, along with a grand prize of $1,000. The 25th annual Tuba Christmas Concert, presented by SmartPark, will return Dec. 10 at 1:30 p.m., making downtown Portland pulsate with the melodic noise of 275 tubas performing a medley of seasonal songs.

    A local Hanukkah tradition also returns Dec. 24 with the lighting of a giant menorah in the center of downtown, lighting up at sundown each night in Director Park. Pioneer Courthouse Square will also host performances by local school, art and dance groups, providing festive entertainment throughout the holiday season. A complete list of holiday events and performances taking place at the square can be found on their website.

    Lastly, while you’re downtown, don’t forget to look up! For more than 20 years, more than 750 trees in downtown Portland get lit up, adding to the holiday festivities downtown. On Yamhill and Morrison streets between Fifth and Sixth avenues, look for a special installation of snowflakes lighting up the night skies.


    The holidays are not available online! Head downtown for the best holiday gifts for the loved ones on your list (and maybe you’ll find some treats for yourself while you’re at it!). Visit longtime favorites Nordstrom, Macy’s, Powell’s Bookstore and Pioneer Place and new businesses including Well Made Goods, featuring cool clothes for rad ladies; Kiriko Made, local producer of modern clothes made from vintage fabrics from Japan; and Hello from Portland, a shop filled with incredible gifts produced by local artists. If all that shopping leaves you hungry, stop at Pine Street Market or experience tea service at the new Headwaters restaurant at the Heathman Hotel to refuel.

    PDX Pop-Up Shops pop up again this year, turning Portland’s vacant retail space into temporary stores where local designers and artists can “set up shop” for the holiday season. The program showcases local design talent, encouraging downtown shoppers to seek out unique gift offerings this holiday season. The shops opened Friday, Nov. 11 at 606 S.W. Ninth Avenue. This year’s local talent includes Faith Hats, offering reclaimed luxury cashmere sweaters, hats and scarves, hand-made locally from 100% recycled materials; Via Raiz, a concept store dedicated to modern Mexican craftsmanship; high-quality custom wood products made by men in the Blanchet House of Hospitality as part of their rehabilitation; and a collective shop of handmade, natural and one-of-a-kind products created by a a diverse group of entrepreneurs brought together by Micro Enterprise Services of Oregon (MESO).

    You can also support small local retailers through Little Boxes, a city-wide shopping event on Black Friday and Small Business Saturday (the Friday and Saturday after Thanksgiving, Nov. 25-26). Embrace the beginning of the holiday season by discovering the quality and variety of Portland’s indie and local retail shopping scene. Unlock 10% off at participating stores, and enter to win a tons of goodies! For more information, visit their website.

    Free parking

    smartparklogoFor three Sundays in December, parking at SmartPark will be the best deal you can find in downtown Portland: free! On Dec. 4, 11, and 18, customers who park at a SmartPark garage can visit the customer service kiosk at Pioneer Place (lower level near Gap) or at Director Park (S.W. Park Ave. and Yamhill St.) from noon-5 p.m. to show their eligible SmartPark ticket for the day and receive a $5 parking voucher to cover that day’s parking cost.

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