Pioneer Courthouse Square is excited to host the Great Figgy Pudding Caroling Competition – a fun, festive, and joyful competition that will bring caroling groups to Portland’s Living Room and extend to a ten-block radius in downtown. The top three caroling groups will hold a “carol-off” at the Square hosted by KGW’s Drew Carney and 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 pm.