Portland’s Public Menorah at The Square
2025-12-15 17:30 - 18:00 (America/Los_Angeles) | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
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 Schedule:

Sunday, December 14 – Festivities begin at 4:00 PM
Monday, December 15 – Thursday, December 18 – 5:30 PM
Friday, December 19 – 3:00 PM
Saturday, December 20 – 6:30 PM
Sunday, December 21 – 5:30 PM

For more information about Hanukkah and a local schedule of events, visit Chabad.org.
Chabad of Oregon offers Jewish education, outreach, and social service programming for families and individuals of all ages, backgrounds, and affiliations.

Ockley Green Middle School Band – Holiday Performances at the Square
2025-12-16 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Ockley Green Middle School Band will be performing holiday music in the Square!

The Tide – Holiday Performances at the Square
2025-12-17 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Singer/Songwriters The Tide will be performing will be performing holiday music in the Square!

Holidays on Downtown’s Transit Mall – Fireside Carolers – Caroling and Coco!
2025-12-17 17:00 - 18:00 | Ben & Jerry’s, 524 SW Yamhill St, Portland, 97204, United States
The Fireside Carolers will be performing holiday music at Ben & Jerry’s, along with free hot coco!
For more information, CLICK HERE.

Holidays on Downtown’s Transit Mall – Sasa Fox at Sixth+Main
2025-12-18 12:00 - 13:00 | 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.

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.”

In Concert on Downtown’s Transit Mall – Ben Grace at Less and More Coffee
2026-03-10 12:00 - 13:00 | Less & More Coffee, 1003 SW 5th Ave, Portland, OR, 97204, United States
At the center of Australian singer-songwriter Ben Grace’s impeccably crafted songs is a story of undoing. Drawn by the roots-driven tradition of Americana to sing the stories that need to be told, Ben’s music hovers in the space between lightness and the depths, wrestling its way through humor and melody to peel back the layers and reveal the naked truth of us. Through the specificity of his own deconstruction, Ben writes into our universal search for belonging, spiritual homecoming, and desire to live seen and unashamed.
For more information, CLICK HERE.

In Concert on Downtown’s Transit Mall – Jay Ringer and the Bells at Pioneer Place
2026-03-12 12:00 - 13:00 | Pioneer Place, 700 SW 5th Ave, Portland, OR, 97204, United States
Trumpeter, pianist, guitarist, and vocalist Jay Ringer does it all with a smooth and peaceful sound that’s very much his own.
For more information, CLICK HERE.

In Concert on Downtown’s Transit Mall – The Xennial at Sixth+Main
2026-03-17 12:00 - 13:00 | SW 6th Ave & SW Main St, Portland, OR 97205, SW 6th Ave & SW Main St, Portland, OR, 97205, United States
The Xennial will be performing at Sixth+Main on Downtown’s Transit Mall!
The Xennial is a music project started in 2018 by Erik Harper out of Portland, Ore. Born in ’82 as a part of the Xennial generation, Erik grew up listening to alternative rock radio and a lot of great 80’s music. The music you hear at a Xennial show includes hard-rocking hits from the likes of Stone Temple Pilots, Green Day, Weezer, Everclear and the Foo Fighters to softer acoustic sounds from the 90s like Dave Matthews Band, Jason Mraz and The Goo Goo Dolls.
For more information, CLICK HERE.

In Concert on Downtown’s Transit Mall – Curtis Reynolds at Pendleton
2026-03-19 12:00 - 13:00 | Pendleton, 825 SW Yamhill St, Portland, OR, 97205, United States
Curtis Reynolds will be performing at Pendleton on Downtown’s transit mall!
Curtis Reynolds is a Portland-based singer/songwriter with a pop/soul influenced vibe express through powerful vocals and acoustic guitar.
