The Square

Enjoy Free Caramel Corn at Mondays on the Mall!
2023-10-09 12:00 - 13:00 (America/Los_Angeles) | Portland Transit Mall
Start your week off right with free caramel corn from Joe Brown’s! Look for the B-line trike along the Transit Mall on Monday compliments of Portland Mall Management. While supplies last.

Mondays on the Mall – Robert Meade at Sixth + Main
2023-10-16 12:00 - 13:00 | SW 6th Ave & SW Main St, Portland, OR 97205, SW 6th Ave & SW Main St, Portland, OR, 97205, United States
Robert Meade will be performing at Sixth + Main on the Transit Mall!
For more information, CLICK HERE.

Mondays on the Mall – Megan McGeorge at US Bancorp Tower
2023-10-16 12:00 - 13:00 | Big Pink, 111 SW 5th Ave #1250, Portland, OR, 97204, United States
Pianist Megan McGeorge will be performing at the US Bancorp Tower on the Transit Mall!
For more information, CLICK HERE.

Scary Dairy in The Square!
2023-10-21 11:00 - 15:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Join The Raven Corps for Scary Dairy in the Square, a very anti-dairy Halloween bash and learn more about Operation: Mind Over Milk, our youth-led campaign to increase access to student, animal, and climate-friendly plant milk in US schools. Feast on delicious dairy-free food from local vegan vendors, dance the afternoon away to a spine-tingling playlist, and don’t forget to come in costume for a chance to win some spooktacular prizes. RSVP here.

Mondays on the Mall – Eugenia Riot at Sixth + Main
2023-10-23 12:00 - 13:00 | SW 6th Ave & SW Main St, Portland, OR 97205, SW 6th Ave & SW Main St, Portland, OR, 97205, United States
Acoustic Blues guitarist Eugenia Riot will be will be performing at Sixth + Main on the Transit Mall!
For more information, CLICK HERE.

Mondays on the Mall – Karyn Ann at Ben Bridge Jewelers
2023-10-23 12:00 - 13:00 | Ben Bridge Jewelers, 801 SW 5th Ave, Portland, OR, 97204, United States
Indie-Folk Singer Songwriter Karyn Ann will be performing at Ben Bridge Jewelers on the Transit Mall!
For more information, CLICK HERE.

Enjoy a Free Caramel Apple at Mondays on the Mall!
2023-10-30 12:00 - 13:00 | Portland Transit Mall
Start your week off right with a free caramel apple from Joe Brown’s! Look for the B-line trike along the Transit Mall on Monday compliments of Portland Mall Management. While supplies last.

Stimson Lumber Tree Arrival
2023-11-08 10:00 - 11:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Celebrate the kick-off of the holiday season in Downtown as Portland’s 75ft tall Douglas-fir is welcomed into Portland’s Living Room! Say hello to Santa and join in the fun of this annual tradition.

39th Annual Tree Lighting Ceremony
2023-11-24 17:30 - 18:30 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Portland’s Tree Lighting will be live in person at Pioneer Courthouse Square the day after Thanksgiving, Friday, November 24th. Featuring a joyful sing-along with Portland’s own Thomas Lauderdale from Pink Martini, local musicians and chorale singers, this event is the highlight of the holiday season in downtown. Join in the celebration as Santa Claus ‘flips the switch’ to illuminate more than 9,500 colorful LED lights on our City’s 75ft Douglas-fir generously donated by Stimson Lumber Company for all to enjoy throughout the holiday season.
Download the official songbook HERE.

The Portland Bazaar at The Square
2023-11-26 11:00 - 16:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Portland Bazaar is popping up at Pioneer Courthouse Square! Along with its main December events, they are bringing some great local shopping and cheer to the Square on one of the busiest weekends of the holiday season. Over 38 vendors will be placed around the big, beautiful tree so visitors to the bazaar can shop outdoors with friends and family.
The Portland Bazaar was started in 2011, with the mission to highlight the numerous skilled makers, artists and small businesses in town. The market has continued to create a space for vendors to showcase and promote their businesses directly to the community. Over the last ten years, the Portland Bazaar has grown to feature over 100 vendors each weekend and truly rounds up the best of the best for local holiday shopping! For more information, CLICK HERE.

Portland Holiday Brew Fest
2023-12-02 11:00 - 21:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Portland Holiday Brew Fest will feature 25+ holiday/winter beers & ciders from around the Northwest. Join us in the heart of downtown at Pioneer Courthouse Square. The event will be under cover in heated tents.
For more information, CLICK HERE.
To purchase tickets for Saturday, December 2nd, CLICK HERE.

Holidays on Downtown’s Transit Mall
2023-12-02 12:00 - 13:00 | Nordstrom @ SW Morrison & Broadway, 701 SW Broadway St., Portland, OR, 97205, United States
The Square and Portland Mall Management bring musician Kris Deelane to perform holiday music in front of Nordstrom at SW Morrison & Broadway!

In partnership with Waterfront Blues Festival

Holidays on Downtown’s Transit Mall
2023-12-02 17:00 - 18:00 | Nordstrom @ SW Morrison & Park, 701 SW Broadway St., Portland, OR, 97205, United States
The Square and Portland Mall Management bring musician Gus Jeffers to perform holiday music in front of Nordstrom at SW Morrison & Park!

In partnership with Waterfront Blues Festival

Portland Holiday Brew Fest
2023-12-03 10:00 - 17:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Portland Holiday Brew Fest will feature 25+ holiday/winter beers & ciders from around the Northwest. Join us in the heart of downtown at Pioneer Courthouse Square. The event will be under cover in heated tents.
For more information, CLICK HERE.
To purchase tickets for Sunday, December 3rd, CLICK HERE.

Holidays on Downtown’s Transit Mall
2023-12-03 12:00 - 13:00 | Charles Schwab, 820 SW Morrison St, Portland, 97205, United States
The Square and Portland Mall Management bring musician Isabel Dammann to perform holiday music in front of Charles Schwab on SW Morrison!

In partnership with Waterfront Blues Festival

Art for Your Heart
2023-12-05 11:30 - 13:30 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Portland creative Larry Yes pops up this Holiday Season in The Square bringing his FREE Art in The Park program Downtown, December 5th – 6th under the shimmering lights of our City’s Tree. Kids, adults, neighbors, and friends are invited to come out to participate in festive holiday card making for loved ones through painting, fun, connection, and music. Cards and art materials provided while supplies last!

Holidays on Downtown’s Transit Mall
2023-12-06 12:00 - 13:00 | Pendleton, 825 SW Yamhill St, Portland, OR, 97205, United States
The Square and Portland Mall Management bring the Rae Gordon Duo to perform holiday music in front of Pendleton on SW Yamhill!

In partnership with Waterfront Blues Festival

Portland’s Public Menorah at Pioneer Courthouse Square
2023-12-07 - 2023-12-15 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Chabad of Oregon will light Portland’s Public Hanukkah menorah at Pioneer Courthouse Square each night of Chanukah.
For more information about Chanukah and a local schedule of events visit CLICK HERE.

The Great Figgy Pudding Caroling Competition
2023-12-08 18:00 - 19:30 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
Pioneer Courthouse Square is excited to host the Great Figgy Pudding Caroling Competition – a fun, festive, and joyful competition that will bring caroling groups to Portland’s Living Room and extend to a ten-block radius in downtown. The top three caroling groups will hold a “carol-off” at the Square hosted by KGW’s Drew Carney and the grand prize winner will be selected by crowd applause and awarded $1,000. Second and third place prizes, as well as the coveted People’s Choice designation, will also be awarded. This FREE caroling competition will be held rain or shine from 6:00-7:30 pm.
Download Your Caroling Map and Event Guide HERE.

Dance Fusion Northwest – Holiday Performances at The Square
2023-12-10 12:00 - 13:00 | 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.

Holidays on Downtown’s Transit Mall
2023-12-12 12:00 - 13:00 | Big Pink, 111 SW 5th Ave #1250, Portland, OR, 97204, United States
Jennifer O’Leary will be performing holiday music at US Bancorp Tower on the Transit Mall!

Holidays on Downtown’s Transit Mall
2023-12-13 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Square and Portland Mall Management bring musicians LaRhonda & Mark Steele to perform holiday music in The Square!

In partnership with Waterfront Blues Festival

Holidays on Downtown’s Transit Mall
2023-12-13 17:00 - 18:00, 2023-12-15 17:00 - 18:00 | OR
Enjoy caroling classics performed by A Cappella singers clad in traditional Old English costumes as they stroll along the transit mall!

Quadraphonnes – Holiday Performances at The Square
2023-12-14 12:00 - 13:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Quadraphonnes will perform holiday music in The Square!

Holidays on Downtown’s Transit Mall
2023-12-14 12:00 - 14:00 | SW 6th Ave & SW Main St, Portland, OR 97205, SW 6th Ave & SW Main St, Portland, OR, 97205, United States
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.
Sasa Fox will be performing holiday music at Sixth+Main!

Holidays on Downtown’s Transit Mall
2023-12-14 17:00 - 18:00 | Portland Transit Mall
The Fireside Carolers will be performing holiday music along the Transit Mall
For more information, CLICK HERE.

Mac Balladeers – Holiday Performances at The Square
2023-12-14 17:00 - 18:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
The Mac Balladeers will be performing holiday music in The Square!

32nd Annual Tuba Christmas Concert
2023-12-16 13:30 - 15:00 | Pioneer Courthouse Square, 701 SW 6th Ave., Portland, OR, 97204, United States
We welcome you back to downtown for this holiday tradition! Experience the sounds of big brass as over 200 tubas play in unison for the 32nd Annual Tuba Christmas Concert in Portland’s Living Room. Attending this seasonal performance is FREE for the public.
Registration to perform in Tuba Christmas is online only. CLICK HERE to register.

Power Pep Band – Holiday Performances at The Square
2023-12-17 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.
