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Full Calendar of Events Lined up at The Square for the Holiday Season, Join Us… Together Downtown

Full Calendar of Events Lined up at The Square for the Holiday Season, Join Us… Together Downtown

In celebration of its 39th holiday season, Pioneer Courthouse Square (The Square) will present nearly two months of free holiday events and cherished traditions that will bring Portland together. Events will begin on Wednesday, November 8 at 10:00 a.m. with the delivery of Portland’s 75-foot tall Douglas fir, generously donated by Stimson Lumber Company.

This press release features multimedia. View the full release here:

The iconic Portland Tree lights up Downtown Portland at The Square, Portland’s Living Room. (Photo: Business Wire)

For 22 years, Stimson Lumber Company has skillfully harvested, delivered, and set up the tree in Portland’s Living Room. To see what it takes to get a 75’ tree to Downtown visit: What does it take to get the tree to The Square? That was the subject of a short produced by Pioneer Courthouse Square in 2021.

The full calendar of events designed to bring Portland Together Downtown for the 2023 Holiday season include:

Wednesday, November 8, 10:00a.m Stimson Lumber Tree Arrival Presented by SmartPark Kick-off the holiday season Downtown with the arrival of Portland’s 75-foot tall Douglas fir, generously donated by Stimson Lumber Company. This year’s tree, grown on sustainable forestlands in Elsie, Oregon, will make its journey to The Square with the help of Redmond Heavy Hauling, a regional trucking company. Upon its arrival to The Square, the tree will be skillfully lifted into place by NessCampbell Crane + Rigging. Join The Square, Portland Parks and Recreation’s Urban Forestry, and fellow Portlanders to celebrate the Tree’s arrival. Santa will be on hand as well, handing out sweet treats and a selection of gift cards from our neighbors at Nordstrom.

November 8 – 22, Daily Tree Building and Light Stringing Once the 75ft Douglas fir Tree is placed at The Square with the help of Ness Campbell Crane, The Square’s Event Production team will skillfully get to work and reattach tree branches utilizing lifts provided by EquipmentShare. After all branches have been attached, Portland’s own Hollywood Lights will adorn the City’s tree with over 9,500 multi-colored LED lights which will illuminate Portland’s Living Room through the New Year.

Friday, November 24, 5:30 p.m. – 6:30 p.m. 39th Annual Tree Lighting Ceremony Presented by SmartPark Portland’s Annual Tree Lighting, presented by SmartPark, invites Portlanders to reunite for a live gathering in Portland’s Living Room the day after Thanksgiving, Friday, November 25, at 5:30 p.m. The ceremony will feature a joyful sing-along with Portland’s own Thomas Lauderdale and Pink Martini, who will be accompanied by talented local musicians and chorale singers. Join in the musical celebration as Santa Claus flips the switch to illuminate more than 9,500 colorful LED lights on Portland’s Tree.

Sunday, November 26, 11:00 a.m. – 4:00 a.m. The Portland Bazaar at The Square The Square is proud to partner with The Portland Bazaar to bring local artisans, makers, and cheer to The Square on the Sunday following Tree Lighting! Nearly 40 vendors will fill The Square. Visitors will be able to shop local for holiday gifts outdoors, under The Tree, with friends and family.

December 2nd 11 a.m. – 9 p.m. & December 3rd 10 a.m. – 5 p.m. Portland Holiday Brew Festival The Square has partnered with True West Presents to bring holiday brews back downtown after a three-year hiatus. The Portland Holiday Brew Fest will fill The Square and features more than 25 holiday and winter beers, ciders, and delicious eats from around the Northwest. Don’t miss this unique holiday celebration under the Tree in the heart of Portland. Festival goers will enjoy spacious heated tents, food and entertainment all while enjoying tasty and frosty brews. Tickets for this festive event can be purchased at

Friday, December 8, 5:30 – 7:30 p.m. The Great Figgy Pudding Caroling Competition The Square is excited to once again bring the Great Figgy Pudding Caroling Competition – a fun, festive musical competition – back to Downtown. This multi-block event brings caroling groups to The Squareand extends into a 10-block radius surrounding The Square. The public can participate in the event by registering to perform with a group or by visiting downtown to vote for your favorite caroling groups. A “carol-off” hosted by KGW’s Drew Carney will be held at The Square for more carols and to award prizes to the top caroling groups. The grand prize winner will be selected by crowd applause and awarded $1,000. Second and third place prizes, as well as the coveted People’s Choice designation, will also be awarded. This FREE caroling competition will be held rain or shine from 5:30 – 7:30 p.m. Team caroling registration is now open to teams of three to 12 carolers per group.

Saturday, December 16, 1:30 p.m. 32nd Annual Tuba Christmas Concert presented by SmartPark The iconic holiday musical tradition returns! Experience the mighty sounds of big brass as over 250 tubas play in harmony for the 32nd Annual Tuba Christmas Concert in Portland’s Living Room. This overwhelmingly popular seasonal performance is free for the public to attend. Tuba players can register online at

December 7 – 15, Time varies depending on the day Portland’s Public Nightly Menorah Lighting Chabad of Oregon will bring Portland’s Public Hanukkah menorah to The Square for its nightly lighting. On the first night, Thursday, December 7th, there will be music, Chanukah foods, and festivities to kick off the eight nights of Chanukah. For more information about Hanukkah and a local schedule of nightly events visit

Beyond these scheduled events, The Square will carry on its tradition of showcasing Live Holiday Art Performances, featuring local musical artists, dancers, schools, bands, and performance groups throughout the holiday season on The Bricks.

In addition, the Holidays on the Mall Series, in partnership with Portland Mall Management Inc., will feature live holiday pop-up performances throughout the month of December along Portland’s Transit Mall, on SW 5th and SW 6th Avenues, to bring holiday joy to the neighboring streets of Downtown.

For a complete schedule of all of these fun holiday events Downtown click here or follow The Square on Facebook, Twitter, and Instagram to stay up to date.

Sponsors and Supporters

The 2023 Holiday Season at Pioneer Courthouse Square is made possible by Smart Park, with additional support from Nordstrom, Stimson Lumber Company, Redmond Heavy Hauling, NessCampbell Crane + Rigging, Portland Parks & Recreation, Prosper Portland, EquipmentShare, Portland Mall Management Inc, Pioneer Place, OSU Foundation, The Oregonian, KGW, and KINK.

About Pioneer Courthouse Square

Pioneer Courthouse Square is where Portland comes together. Through stewardship and strategic vision, the nonprofit ensures that The Square remains the foundation of a diverse and thriving downtown, and in turn a better Portland. With more than 300 events per year, The Square is home to many of Portland’s favorite community traditions including concerts, festivals of food and drink, and cultural celebrations. Through a variety of public and private partnerships, Pioneer Courthouse Square operates within an annual budget of $2.2M composed of cash and in-kind donations.

For photos, b-roll, or interviews, contact: Theresa Vetsch-Sandoval [email protected] 503-776-0951

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Printable Blank Calendar Templates - Wiki Calendar