Soulful vocalist and guitarist Jordan Sings will be performing in front of Tory Burch at Pioneer Place on Downtown’s Transit Mall! Cutting his teeth as a street performer in Portland,...

The Beat Goes On Marching Band will be will be performing holiday music in The Square! The Beat Goes On is Portland, Oregon's international award-winning all-adult marching band.  TBGO is...

Ukrainian Community Choir Lisova Pisnya will be will be performing holiday music in The Square!

Chabad of Oregon invites the community to celebrate Hanukkah with the annual lighting of Portland’s Public Menorah at Pioneer Courthouse Square, Sunday, December 14 – Sunday, December 21, 2025. Lighting...

Saxophone duo David Trotter and Jill Pex will be will be performing holiday music in The Square! For more information, CLICK HERE.

The Fireside Carolers will be performing holiday music along the Transit Mall! For more information, CLICK HERE.  

The Moonglow Quartet will be performing holiday music in the Square!  

Enjoy caroling classics performed by A Cappella singers clad in traditional Old English costumes as they stroll along Downtown's Transit Mall!