Holiday Tree Lightings & Festivals in Portland

Even though big retail stores have had Christmas decorations out since the end of October, for many of us, the real harbinger of the holidays is the annual holiday tree lighting. And no matter where you live in Portland, there’s a tree lighting or festival just an easy bus ride away. I’ve even included a couple lightings in the nearby cities of Gresham and Milwaukie. Each listing below includes the closest TriMet stops to the corresponding tree lighting. Take advantage of TriMet’s trip planner to enter your starting location and the event’s address as the ending location for a detailed trip itinerary. Happy Holidays!

1. Pioneer Courthouse Square 701 SW 6th Ave., Portland, OR 97204

Friday, November 28th 5:30 – 6:30 p.m. 


Photo by Travel Portland

“Thousands of Portlanders will gather at the Square to celebrate 30 years of lighting of the spectacular 75ft Tree provided by Stimson Lumber Company.  This year’s event will feature a holiday sing-a-long featuring Thomas Lauderdale with members of Pink Martini, “Oregon’s Own” 234th Army Band and the Pacific Youth Choir.  A pre-show with the NW Community Gospel Choir will begin at 5:00pm.” Click here for more information.

2. Gresham Arts Plaza 401 N.E. Second StGresham, OR 97030

Saturday, November 29th 5:00 – 6:30 p.m.

Photo by Daniel from Sacramento on flickr

“Gresham’s kick-off to the holiday season, the Spirit of Christmas will feature a free program full of family-friendly fun, including performances by local musicians, hot cocoa and treats. Santa Claus will be at the event and Mayor Shane Bemis will lead the lighting of the 60-foot Ponderosa pine tree.” Click here for more information.

3. Jamison Square 810 NW 11th Ave, Portland, OR 97209

Saturday, November 29th 4:00 – 6:00 p.m.


Photo by Randy Kashka on flickr

“Enjoy a holiday light show and festive caroling in Jamison Square, before taking in the area’s best dining and shopping. Plus, the first 50 guests receive a FREE logo umbrella!” Click here for more information.

4. Mississippi Commons 3731 N Mississippi , Portland, Oregon 97211

Saturday November 29th 5:00 – 6:00 p.m.


Photo by Mississippi Ave.

“Join Mississippi Ave on Saturday, November 29th at Mississippi Commons for the annual holiday tree lighting, featuring an exclusive performance by children’s performer Mr. Ben and the Portland Youth Ukulele Orchestra. The Ukeladies PDX open the show. Sing along with free songbooks and be treated to free tea and cookies from Stash Tea and New Seasons Market.” Click here for more information.

5. Providence Festival of Trees Oregon Convention Center, Hall A, 777 NE Martin Luther King Jr. Blvd., Portland, OR 97232

Friday, December 5th 10:30 a.m. – 5:00 p.m. and Saturday, December 6th 9:00 a.m. – 5:00 p.m.


Photo by Providence Festival of Trees Portland

“This wondrous event helps usher in the holiday season with visions of beautifully adorned trees and wreaths, smells of Christmas cookies and sounds of jingle bells, and, all around, the spirit of giving. Festival-goers will get to experience these delights at the Oregon Convention Center.” Click here for more information.

6. Milwaukie Umbrella Parade and Tree Lighting 10722 SE Main St, Milwaukie, OR 97222

Saturday, December 6th 3:30-5:00 p.m.


Photo by Metro Parent’s PDX Kids Calendar 

“Milwaukie’s Umbrella Parade & Tree Lighting Ceremony, the popular event where participants decorate their umbrellas and compete for prizes, is set for Sat., Dec. 6, 2014. Staging for the parade begins at 3:30 p.m. at the Portland Waldorf School’s south parking lot, (21st Avenue and Monroe Street) and the Tree Lighting Ceremony follows the parade at City Hall (Jackson and Main) around 4:45 p.m. Umbrella contest categories include: most creative, most festive and most Milwaukie. Santa Claus is scheduled to be back again this year, and will visit with children at City Hall during the Tree Lighting Ceremony where hot cocoa and cookies will be served. This year attendees are asked to bring a new, unwrapped toy to donate to the Annie Ross House, the emergency shelter for families that’s located in Milwaukie. Milwaukie’s emergency response team volunteers (CERT) is helping with parade staging and logistics, and as in year’s past, the Milwaukie High School band will lead the parade.” Click here for more information.

7. St Johns Winterfest St. Johns Plaza, N Lombard & N Philadelphia, Portland, OR 97203

Sunday, December 7th 1:00 – 6:00 p.m.

Photo by Kilmi on flickr

“Every year this is a pretty cool event, but this year it will be extra-special, as Winter Fest is raising funds for the Community of Hope. This year’s event will include the St. Johns Winter Farmers Market, vendors in the North End Winter Market, and living legends like Tiny Tim and Scrooge. The James John Café will put on a Winter Feast, there will be a tree lighting at dusk, music and shopping.” Click here for more information.

Article by Stephanie Paris

Cover photo by Travel Portland


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s