Holiday Events

There’s always something festive happening Downtown this season. Join us for holiday classics like the Pioneer Square Tree Lighting or new, soon-to-be favorites like the Rose City Trombones. Enjoy all the wonders of the season Downtown.

Yarn bombings

Nov. 14 – Dec. 7

Some of the Pioneer District’s most iconic statues are getting dressed up for the holidays with ugly-sweater-inspired yarn bombing from local fiber artists. The festive knitwear will be installed in the first weeks of the holiday shopping season. Make sure to get pictures with your favorite pieces and help spread the warm and cozy cheer using the hashtag #UglySweaterPDX.

Pioneer Courthouse Square, SW Morrison and Yamhill streets, SW 5th and 6th avenues

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Warm Clothing Drive

Nov. 14 – Dec. 20

To help make other people’s holidays brighter, we’ll be accepting warm clothing donations for Transitions Projects. Each year, the organization helps more than 10,000 people transition from homeless to housing. Every piece of new or gently used warm clothing is appreciated, and donations can be made in donation boxes at the following locations:

  • 1000 Broadway building lobby, 1000 SW Broadway
  • Portland Business Alliance, 200 SW Market St. Suite 150
  • Boys Fort, 902 SW Morrison
  • Pioneer Place Mall Guest Services desk, 700 SW 5th Ave.

Menorah Lighting at Director Park

Wednesday, Nov. 27, 4:30-6:30 p.m.

Chabad of Oregon, Jewish Family & Child Services and the Oregon Food Bank are partnering together for the 30th Annual Menorah Lighting, which will feature children’s activities, a canned food drive and more.

Director Park, 815 SW Park Ave.

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Thanksgiving Openings/Black Friday

Thursday, Nov. 28 at 8 p.m.

Savvy shoppers can get a head start on the holiday shopping season and nab Black Friday deals earlier than ever this year. After finishing their holiday meals (and post-meal naps), bargain-hunters can start saving at Macy’s and Target at 8 p.m. on Thanksgiving night. To really fight the feast-induced slumber, Starbucks at Pioneer Courthouse Square will be open Thanksgiving (4:30 a.m.-11 p.m.) and Black Friday (4:30 a.m.-12 a.m.).

Little Boxes

Nov. 29-30, 10 a.m.-7 p.m.

Back for its third year, Portland’s local Black Friday and Small Business Saturday event includes more than 100 businesses citywide, like downtown favorites Tender Loving Empire, underU4men, Crafty Wonderland and Bridge & Burn. Find gifts for everyone on your list, unlock discounts and enter to win raffle prizes at each store you visit.

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My Macy’s Holiday Parade

Friday, Nov. 29, 9-11 a.m.

Straight from the North Pole, Santa Claus leads the annual My Macy’s Holiday Parade as it weaves through the streets of downtown Portland with 25 inflatable floats, local middle and high school marching bands, nearly 650 costumed characters and more. Immediately after, Santa arrives at the downtown Macy’s store to open Santaland for the holiday season.

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Macy’s Santaland

Nov. 29 – Dec. 24

Santa arrives at Macy’s Santaland at 11 a.m. the day after Thanksgiving, following the holiday parade. Stop by to get pictures with Santa and check out the restored original monorail next to the train garden.

Macy’s, 621 SW 5th Ave.

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Tea at The Heathman

Nov. 29 – Jan. 5 at 11 a.m., 1 p.m. and 3 p.m.

Join in the long-standing and cherished holiday tradition of high tea at The Heathman’s historic tea court, decked in yuletide splendor. Chef Michael Stanton’s culinary team presents a Northwest twist on the English tradition.

The Heathman Restaurant & Bar, 1001 SW Broadway

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#UglySweaterPDX contest

Dec. 2-17

Don your ugliest holiday apparel and enter Downtown Portland’s #UglySweaterPDX contest via Instagram, Twitter or Facebook. There will be weekly winners, and Portland’s Ugliest Sweater will win the grand prize on National Ugly Sweater Day (Dec. 20).

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Holiday Ale Festival

Dec. 4-8, 11 a.m.-10 p.m. (festival closes at 5 p.m. Sunday, Dec. 8)

Held every year in the heart of downtown, beneath the boughs of the holiday tree in Pioneer Courthouse Square, the Holiday Ale Festival keeps holiday revelers merry with more than 50 strong winter warmer ales. There are more than 50 of these rich, robust beers, including many created especially for the festival.

Pioneer Courthouse Square, 701 SW 6th Ave.

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Magic Moments

Thursdays, Dec. 5, 12 & 19

Downtown’s Sidewalk Ambassadors will be at Boys Fort three Thursday afternoons in December helping make the holidays magical for downtown shoppers. Stop by to check out unique gift options and you just might end up with free parking, giveaways and other fun goodies to surprise and delight.

Boys Fort, 902 SW Morrison

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Rose City Trombones

Dec. 7 at 10 a.m.

Not to be outdone by their larger, more established brass cousins the tubas, Portland’s trombones are banding together for their first holiday concert. More than a dozen classically trained trombonists will play holiday favorites to serenade downtown shoppers.

Director Park, 815 SW Park Ave.

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Ugly Sweater Decorating Party

Saturday, Dec. 7, 11 a.m. – 2 p.m.

Take a break from your holiday shopping to stop by Punch Bowl Social and make your very own festive holiday sweater — the “ugly” is optional! Downtown Portland will provide sweater-decorating materials and festive refreshments.  Plus, get a free parking voucher when you park in a SmartPark garage!

Punch Bowl Social in Pioneer Place, 340 SW Morrison, 3rd floor

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Christmas Ships on the Willamette

Dec. 10, 12, 17 & 19 at 7 p.m. and Dec. 15 & 21 at 5 p.m.

Enjoy the ambiance as ships covered in light displays float down the Willamette River during December. The owner-decorated and -operated private ships bring the holiday cheer to the rivers on two routes that pass downtown’s shores. Since 1954, the Christmas Ships have been a Portland holiday tradition, with around 60 boats in the flotilla each year.

West bank of the Willamette River

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Tuba Christmas Concert

Dec. 14 at 1:30 p.m.

The 23rd annual Tuba Christmas Concert at Pioneer Courthouse Square is one of Portland’s most iconic holiday celebrations. Sit back and enjoy the free concert as the sweet song of more than 250 tubas fills the air on one of the most popular shopping days of the season.

Pioneer Courthouse Square, 701 SW 6th Ave.

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Portland Cello Project Winter Sweater Spectacular

Friday, Dec. 20 at 7 p.m.

The Portland Cello Project’s annual holiday performance will feature compositions and arrangements of winter-themed music from various cultures and periods, all celebrating the release of Portland Cello Project’s new EP Winter (The Best Nine Months of the Year). Special guests will include Nancy Ives, principal cellist of the Oregon Symphony, local singers Laura Gibson and Laura Veirs, and legendary Tuscon songwriter Howe Gelb.  Enter to win tickets to see the show with our #uglysweaterpdx contest!

Arlene Schnitzer Concert Hall, 1037 SW Broadway

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