The Square

Holidays on Downtown’s Transit Mall – Sasa Fox at Sixth+Main
2025-12-18 12:00 - 13:00 (America/Los_Angeles) | SW 6th Ave & SW Main St, Portland, OR 97205, SW 6th Ave & SW Main St, Portland, OR, 97205, United States
Sasa Fox will be performing at Sixth+Main on Downtown’s Transit Mall! Portland based songwriter Sasa Fox brings a splash of color to the dreary Northwest with clever pop songs written about the spectrum of emotions and experiences that are integral to being human.

Sam Barlow High School – Holiday Performances at The Square
2025-12-19 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Sam Barlow High School will be performing holiday jazz music in The Square!

Holidays on Downtown’s Transit Mall – The Dickens Carolers
2025-12-19 17:00 - 18:00, 2025-12-23 17:00 - 18:00 | OR
Enjoy caroling classics performed by A Cappella singers clad in traditional Old English costumes as they stroll along Downtown’s Transit Mall!

Power Pep Band – Holiday Performances at The Square
2025-12-20 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Power Pep Band will perform an energetic and festive holiday set in The Square!
We are the Power Pep Band. We are an fun-loving entertaining crowd pleasing band based on the traditional college pep bands. We play rock and roll as well many seasonal songs. We have been together for over 20 years and loving every minute of it. We have been performing around the Pacific Northwest and many places in the USA as well as Canada. We aim to have fun and include our audiences in that fun.
For more information, CLICK HERE.

Holidays on Downtown’s Transit Mall – MC Shoehorn at Pendleton
2025-12-20 17:00 - 18:00 | Pendleton, 825 SW Yamhill St, Portland, OR, 97205, United States
MC Shoehorn will be performing at Pendleton on Downtown’s Transit Mall! Shoehorn began his musical journey in 1979 as a street performer in New Orleans, where he got his first pair of tap shoes. He went on to perform in 30 countries and most of the USA, and has released 6 full-length CDs featuring tap dance on his original compositions and his arrangements of show tunes. He plays a lot of instruments but is best known for simultaneously playing sax and tap dancing.

Get A Life Marching Band – Holiday Performances at The Square
2025-12-20 17:00 - 18:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Join Get A Life Marching Band for a high-energy holiday performance in The Square!
Get a Life Marching Band was founded in 1994 as an all adult (chronologically) marching band to play in local neighborhood parades. For more information, CLICK HERE.

Holidays on Downtown’s Transit Mall – Jordan Sings at Pioneer Place
2025-12-21 12:00 - 13:00 | Pioneer Place, 700 SW 5th Ave, Portland, OR, 97204, United States
Soulful vocalist and guitarist Jordan Sings will be performing in front of David Yurman at Pioneer Place on Downtown’s Transit Mall! Cutting his teeth as a street performer in Portland, Oregon, Jordan Sings has perfected his own brand of singer-songwriter pop. With influences from Ed Sheeran, John Mayer and Tracy Chapman, Jordan combines raw life stories with catchy and inviting arrangements.
For more information, CLICK HERE.

The Beat Goes On Marching Band – Holiday Performances at The Square
2025-12-21 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
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 renowned for its upbeat attitude, emphasis on audience interaction, and feel-good selections featuring a high-energy, brassy style. The band will be presenting an eclectic mix of holiday tunes and other favorites.
The group has performed alongside Plymouth Rock, in Alaska’s largest parade, on the floor of the Oregon House of Representatives, at an 18th century European castle, in front of the Alamo … and atop the Great Wall of China.
For more information, CLICK HERE.

Ukrainian Community Choir Lisova Pisnya – Holiday Performances at The Square
2025-12-21 17:00 - 18:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Ukrainian Community Choir Lisova Pisnya will be will be performing holiday music in The Square!

David Trotter and Jill Pex – Holiday Performances at The Square
2025-12-22 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Saxophone duo David Trotter and Jill Pex will be will be performing holiday music in The Square!
For more information, CLICK HERE.

Holidays on Downtown’s Transit Mall – Fireside Carolers
2025-12-22 17:00 - 18:00 | Portland Transit Mall
The Fireside Carolers will be performing holiday music along the Transit Mall!
For more information, CLICK HERE.

Moonglow Quartet – Holiday Performances at the Square
2025-12-23 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Moonglow Quartet will be performing holiday music in the Square!

New Year’s Eve Downtown, Live Drones, Dancing and Fun in The Square
2025-12-31 20:00 - 2026-01-01 00:30 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
PORTLAND, LET’S RING IN 2026 TOGETHER!
Portland’s amazing New Year’s Eve dance party and drone show is BACK for a second spectacular year!
Celebrate New Year’s Eve in the Heart of Downtown with two FREE live drone shows and a large-scale, all-ages dance party at The Square! The celebration kicks off at 8pm with an epic outdoor dance party from Portland’s own Video Dance Attack spinning the hottest hits of the past decades with music videos projected onto giant screens. The excitement continues with the first family-friendly drone show at 9pm, followed by the final countdown drone display at Midnight to welcome 2026. This event is FREE to the public with delicious food, hot cocoa and mocktails available for purchase throughout the night. SEE YOU DOWNTOWN ON NYE, PORTLAND!
8:00pm Video Dance Attack Party Begins!
Dance hits of the past decades with music videos projected onto giant screens
Food and beverages available for purchase
9:00pm Drone Show #1
The dance party continues
10:00pm The fun keeps going with Music, Videos and Dancing!
11:50pm Drone Show #2 Countdown to MIDNIGHT
12:30am Party Wraps up!
Park Smartly on New Year’s Eve or take TriMet. Travel around Downtown Portland will be free on TriMet buses, MAX and the Portland Streetcar after 8PM.
Drone operations are weather dependent due to safety regulations.
