Holidays on Downtown’s Transit Mall – Fireside Carolers
2025-12-22 17:00 - 18:00 (America/Los_Angeles) | 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!

Holidays on Downtown’s Transit Mall – The Dickens Carolers
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!

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.

11th Annual Portland Winter Light Festival
2026-02-06 18:00 - 22:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Square is proud to partner with the Portland Winter Light Festival as a central Downtown anchor location, helping to broaden the Festival’s accessibility. For more than 40 years, The Square, also known as Portland’s Living Room, has served as the open public gathering space in the heart of our downtown, welcoming more than 1.3 million visitors each year.
This citywide celebration illuminates Portland and helps to build community by bringing people together through shared moments of human connection to experience immersive art and innovation. The Square’s diverse events play a vital role in keeping downtown busy, healthy, and vibrant, and the Festival creates meaningful opportunities for artists, technologists, culture bearers, local businesses, and visitors to engage and celebrate Portland’s creative spirit.
This collaborative community initiative aligns with The Square’s mission to serve as the foundation of a diverse and thriving downtown, helping to move Portland forward together.
This year’s theme “All The Little Things” explores how the smallest things can carry the greatest weight—how insects have more power when they work together. How a tiny stone can reflect light, and how one memory can set you on a path to the future.
For a full artist roster, interactive map, and more, CLICK HERE.
