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 events
Celebrating more than 30 years, “Portland’s Living Room” is the place to be for free, family-friendly holiday events and activities.
- The season begins with the Stimson Lumber Tree Arrival on Nov. 9, complete with MarchFourth marching band and a visit from Santa.
- The Annual Tree Lighting Ceremony will be held the day after Thanksgiving (Friday, Nov. 24) at 5:30 p.m. The event will include a joyful community sing-a-long of holiday songs.
- The Great Figgy Pudding Caroling Competition, presented by Portland Mall Management, Inc., brings together caroling groups of all ages. This fun and festive competition will be held Friday, Dec. 8 from 5:30–7:30 p.m. Prizes go to the top caroling groups (along with a grand prize of $1,000).
- The 27th Annual Tuba Christmas Concert, presented by SmartPark, will be held Saturday, Dec. 9, at 1:30 p.m. Downtown will pulse with big brass as more than 275 tubas perform a medley of seasonal songs at this free concert.
Pioneer Courthouse Square will once again feature 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 Pioneer Courthouse Square can be found by visiting ThesquarePDX.org.