The Square

In Concert on Downtown’s Transit Mall – Hayley Lynn at Pioneer Place @ Nike
2025-10-28 12:00 - 13:00 (America/Los_Angeles) | Pioneer Place @ Nike, 700 SW 5th Ave, Portland, OR, 97204, United States
Soulful Singer-Songwriter Hayley Lynn will be performing at Pioneer Place in front of Nike on Downtown’s Transit Mall!
For more information, CLICK HERE.

In Concert on Downtown’s Transit Mall – Johnny Franco and His Real Brother Dom at Pioneer Place @ David Yurman
2025-10-30 12:00 - 13:00 | Pioneer Place Main Entrance, 700 SW 5th Ave, Portland, OR, 97204, United States
Johnny Franco and his Real Brother Dom will be performing at Pioneer Place in front of David Yurman on Downtown’s Transit Mall! Walk down any street in Portland, Oregon and you are sure to encounter a mustachioed Brazilian rock and roll troubadour named Johnny Franco and (his real brother) Dom. Recently moving from Sao Paulo, the duo has developed a cult following in Portland for their high energy performance and music. The self-proclaimed Professional Entertainer has sold out his last two headline shows at the Doug Fir in Portland, Oregon.

Stimson Lumber Tree Arrival
2025-11-12 11:00 - 12:30 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Kick-off of the holiday season Downtown as Portland’s 75ft tall Douglas-fir Tree is welcomed to Portland’s Living Room! Say hello to Santa, enjoy free hot chocolate and join in the fun of this annual tradition.

41st Annual Tree Lighting Ceremony Presented by SmartPark
2025-11-28 17:30 - 18:45 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
A joyful community sing-along led by Portland’s own Thomas Lauderdale of Pink Martini with many of Portland’s finest musical artists and chorale singers. Portland’s Tree Lighting Ceremony is the highlight of the holiday season in downtown. Join in this holiday tradition as Santa Claus ‘flips the switch’ to illuminate nearly 10,000 colorful lights on our City’s Tree that will shine bright throughout the holiday season.
To download the official songbook, CLICK HERE.

Portland Holiday Brew Fest
2025-12-05 17:30 - 22:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Portland Holiday Brew Fest returns on December 5th & 6th, bringing winter cheer and delicious beer to The Square! Join us under covered, heated tents to enjoy 30+ holiday/winter beers & ciders from around the Northwest, plus music from vinyl DJs and a variety of cozy winter foods.
For more information and tickets, CLICK HERE.

Holidays on Downtown’s Transit Mall – Machado Mijiga at Less and More Coffee
2025-12-09 12:00 - 13:00 | Less & More Coffee, 1003 SW 5th Ave, Portland, OR, 97204, United States
Classically-trained multi-instrumentalist Machado Mijiga brings his unique brand of hip-hop and electronica-infused remixes to Less and More Coffee on Downtown’s Transit Mall.
For more information, CLICK HERE.

Holidays on Downtown’s Transit Mall – Story & Tune at 6th + Main
2025-12-10 12:00 - 13:00 | SW 6th Ave & SW Main St, Portland, OR 97205, SW 6th Ave & SW Main St, Portland, OR, 97205, United States
Aussie singer-songwriter Ben Grace and Californian poet Karyn Thurston met for the first time weeks after they first said I love you, a blush-worthy whirlwind love story that landed them in a creative partnership writing a torrent of original songs. Story & Tune is the marriage of Karyn’s words and Ben’s melodies (though they’ve been known to switch roles from time to time.) Driven by folk-Americana’s long history of lyrical storytelling, the harmony-driven duo’s songs are a unique blend of heart, ache, and laughter, all grounded in the unwavering belief that belonging is an essential human right.
For more information, CLICK HERE.

Dance Fusion Northwest – Holiday Performances at The Square
2025-12-11 17:00 - 18:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Dance Fusion Northwest will be will be performing to holiday music in The Square!
For more information, CLICK HERE.

11th Annual Great Figgy Pudding Caroling Competition
2025-12-12 18:00 - 20:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The 11th Annual Great Figgy Pudding Caroling Competition, hosted by KGW’s Drew Carney, is a fun, festive, and joyful competition bringing hundreds of carolers to a ten-block radius the surrounds Portland’s Living Room®. Carolers perform in front of Downtown’s favorite nearby shops, restaurants, and hotels with the top three caroling groups holding a “carol-off” at The Square. Members of the public can participate in this FREE event by registering to perform with a caroling group or by visiting performing caroling groups to vote for your favorite.
To register your caroling group, CLICK HERE.
Download the Figgy Pudding Caroling Map HERE.

34th Annual Tuba Christmas Concert
2025-12-13 13:30 - 15:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
This iconic, quirky and heart-warming holiday musical tradition is back! Experience the mighty sounds of big brass as nearly 300 tubas play in harmony while the crowd is invited to sing along. This live performance is one of the largest in the country with tuba participants travelling from all points of Oregon to join in this festive event with a crowd of thousands. Attending this seasonal performance is FREE for the public.
Registration to perform in Tuba Christmas is online only. To register to perform, CLICK HERE.
Thank you to Oregon State University Foundation for underwriting registration fees for the fourth consecutive year. This generous donation provides hundreds of Tuba players barrier-free access to performing in this community event.

Portland’s Public Menorah at The Square
2025-12-14 16:00 - 17:30 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Chabad Center for Jewish Life 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.
First Night Celebration – Sunday, December 14 at 4:00 PM
Live music, traditional Chanukah foods, dignitaries, and family festivities will launch eight nights of light and joy. The menorah will be lit at 5:30 PM.
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

To register to attend the event, CLICK HERE.
Chabad Center for Jewish Life offers Jewish education, outreach, and social service programming for families and individuals of all ages, backgrounds, and affiliations.

Holidays on Downtown’s Transit Mall – The Tide at Big Pink
2025-12-15 12:00 - 13:00 | Big Pink, 111 SW 5th Ave #1250, Portland, OR, 97204, United States
Singer/Songwriters The Tide will be performing at Big Pink on Downtown’s Transit Mall!

The HoneyBees – Holiday Performances at The Square
2025-12-15 17:00 - 18:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The HoneyBees will be will be performing to holiday music in The Square!
For more information, CLICK HERE.

Portland’s Public Menorah at The Square
2025-12-15 17:30 - 18:00 | 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!
