Holiday events at Pioneer Courthouse Square

Portland’s living room bustles with free, festive activities every holiday season.

DowntownTreeLighting_DmitriyMollaThe region's largest Christmas tree has a lighting celebration every holiday season.
Dmitriy Molla

Whether you prefer classic caroling, quirky celebrations or bustling shops, downtown Portland’s holiday wonderland will keep you merry and bright. This hub holds indie shopping events, family-friendly festivities and free performances — all within a few blocks’ radius. That means no driving from neighborhood to neighborhood, since it’s all right here.

Pioneer Courthouse Square holiday 2018 events

Pioneer Courthouse Square is the place to be in downtown this holiday season for free, family-friendly holiday events, activities, performances and tradition.

  • The season begins with the Stimson Lumber Tree Arrival on Nov. 9, complete with Santa, as the city’s tree makes its way down Southwest Sixth Avenue to “Portland’s Living Room.”
  • The 34th Annual Tree Lighting Ceremony, presented by SmartPark, will be held the day after Thanksgiving (Friday, Nov. 23) at 5:30 p.m. The event will include Portland’s largest community sing-a-long led by Thomas Lauderdale of Pink Martini, as well as the lighting of the spectacular and stately 75-foot Douglas fir tree adorned with more than 14,000 colorful lights.
  • 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 on Friday, Dec. 7, 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 28th Annual Tuba Christmas Concert, presented by SmartPark, will be on Saturday, Dec. 8, at 1:30 p.m. Once again, downtown will pulse with the melodic sounds of big brass as nearly 300 tubas players perform a medley of seasonal songs in unison during this free performance.

Pioneer Courthouse Square will also continue the tradition of performances by local school, art and dance groups, providing festive entertainment throughout the holiday season. Find a complete list of holiday events and performances taking place at Pioneer Courthouse Square at

Pioneer Courthouse Square, Inc., is an award-winning nonprofit organization whose mission is to manage Downtown’s central public gathering space known as Portland’s Living Room, to achieve an active and healthy downtown core. Hosting more than 300 programmed events each year, Pioneer Courthouse Square operates with an annual budget of $2.2 million composed of cash and in-kind donations. To view a full schedule of events at the Square visit

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