Holidays on Downtown’s Transit Mall – Jordan Sings at Pioneer Place
2025-12-21 12:00 - 13:00 (America/Los_Angeles) | 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!

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.

In Concert on Downtown’s Transit Mall – Hayley Lynn at Sixth+Main
2026-02-17 12:00 - 13:00 | SW 6th Ave & SW Main St, Portland, OR 97205, SW 6th Ave & SW Main St, Portland, OR, 97205, United States
Soulful Singer-Songwriter Hayley Lynn will be performing at Sixth+Main on Downtown’s Transit Mall!
For more information, CLICK HERE.

In Concert on Downtown’s Transit Mall – Pablo Rivarola at Nordstrom
2026-02-19 12:00 - 13:00 | Nordstrom @ SW Morrison & Broadway, 701 SW Broadway St., Portland, OR, 97205, United States
Jazz trumpeter Pablo Rivarola will be performing at Nordstrom on Downtown’s Transit Mall!
For more information, CLICK HERE

4 Years of Valor in Ukraine
2026-02-22 14:00 - 18:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Ukrainian community is coming together for a heartfelt event to celebrate the resilience of their shared culture, honor the memory of veterans, support Ukrainian refugees, and celebrate the resilience of their shared culture. This gathering offers a space for reflection, grief, and unity, as attendees commemorate the sacrifices made for Ukraine’s freedom. Through cultural traditions, music, and connection, the event strengthens bonds and provides comfort to all affected by the ongoing challenges of war.
For more information, CLICK HERE.

In Concert on Downtown’s Transit Mall – MC Shoehorn at Pioneer Place
2026-02-24 12:00 - 13:00 | Pioneer Place Main Entrance, 700 SW 5th Ave, Portland, OR, 97204, United States
MC Shoehorn will be performing at Pioneer Place 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.

In Concert on Downtown’s Transit Mall – Gabe Hess at Big Pink
2026-02-26 12:00 - 13:00 | Big Pink, 111 SW 5th Ave #1250, Portland, OR, 97204, United States
Gabe Hess will be performing at Big Pink on Downtown’s Transit Mall! Gabe Hess is a singer/songwriter, composer, and arranger based out of the Pacific Northwest. Gabe first began working in the music industry during his college years, performing in clubs in Boise Idaho with several different bands and collaborations. In 2018, Gabe released his first EP titled “Working” which was comprised of an eclectic group of original songs spiced with styles from country to classic soul.
For more information, CLICK HERE.

In Concert on Downtown’s Transit Mall – Eric John Kaiser at Less and More Coffee
2026-03-03 12:00 - 13:00 | Less & More Coffee, 1003 SW 5th Ave, Portland, OR, 97204, United States
Eric John Kaiser will be performing at Less and More Coffee on Downtown’s transit mall! Known as The French Troubadour, Parisian-born Eric John Kaiser is a singer-songwriter reimagining French music through an Americana lens. Eric was born in the southern outskirts of Paris, in small town called Verrières-le Buisson, and began learning guitar when he was 10 years old. After years of a classical music education, he found a teacher that opened him up to the music of the Beatles and Rolling Stones. He began writing songs in his adolescence, using music as both a diary to channel his experiences and as his personal legacy. After performing over 350 concerts in France, Eric John Kaiser fell in love with a girl, a romance which would bring him to Portland, Oregon where he is currently based. His songs resonate with a genuine Americana rhythm, like galloping across the vast plains on horseback, with a western lap steel guitar playing dirty roadhouse blues.
For more information, CLICK HERE.

In Concert on Downtown’s Transit Mall – Gretta Seabird at Sixth+ Main
2026-03-05 12:00 - 13:00 | SW 6th Ave & SW Main St, Portland, OR 97205, SW 6th Ave & SW Main St, Portland, OR, 97205, United States
Gretta Seabird will be performing at Sixth+ Main on Downtown’s transit mall!
Gretta Seabird began with a simple songwriting challenge. Every two weeks, Jeremiah Brunnhoelzl would email guitar tracks from his flat in Brooklyn, NY to Lee McDonnell in Portland, OR, who would then give herself a mere day to pen down lyrics and melody. As the songs formed at a rapid, yet natural pace, the pair began to believe in the poetry they were creating, in the little moments caught in time. Thus, Gretta Seabird was formed, and with it the debut EP “Cycling.”

Holi Festival of Colors
2026-04-04 12:00 - 16:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Portland Holi returns! Come dressed in white and play with color powder to celebrate India’s festival HOLI to welcome Spring! For more information, CLICK HERE.

2026 Chinese Festival
2026-08-01 11:00 - 18:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Join the Oregon Chinese Coalition for the 2026 Chinese Festival in the Square! Experience the richness of Chinese American culture with non-stop performances, authentic Chinese food and beverages, and family-friendly cultural activities.
For more information visit pdxchinese.org.

India Festival 2026
2026-08-23 10:30 - 20:30 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
India Festival brings India to the Square! This festival is a celebration of India’s Independence Day with live music, dance, food and other entertainment. India Festival is hosted by the India Cultural Association, a non-profit dedicated to enhancing Indian cultural awareness. For more information, CLICK HERE.
