Celebrate the kick-off of the holiday season in Downtown as Portland’s 75ft tall Douglas-fir is welcomed into Portland’s Living Room! Say hello to Santa and join in the fun of...

Portland's Tree Lighting will be live in person at Pioneer Courthouse Square the day after Thanksgiving, Friday, November 29th. Featuring a joyful sing-along with Portland’s own Thomas Lauderdale from Pink...

The Portland Bazaar is back at The Square! Along with its main December events, they are bringing some great local shopping and cheer to The Square on one of the...

The Portland Holiday Brew Fest will feature 25+ holiday/winter beers & ciders from around the Northwest. Join us in the heart of downtown at Pioneer Courthouse Square. The event will...

The Portland Holiday Brew Fest will feature 25+ holiday/winter beers & ciders from around the Northwest. Join us in the heart of downtown at Pioneer Courthouse Square. The event will...

The Portland Holiday Brew Fest will feature 25+ holiday/winter beers & ciders from around the Northwest. Join us in the heart of downtown at Pioneer Courthouse Square. The event will...

Portland Oregon natives and identical twins Acoustic Minds will be performing holiday music in the Square! For more information, CLICK HERE.

The Jefferson Dancers will be dancing to holiday music in the Square!  

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...