As the days grow shorter and the rain settles in, Portland knows exactly how to chase away the gloom: with thousands of twinkling lights and joyful community gatherings. This holiday season, the city and its surrounding neighborhoods are gearing up for a series of tree lighting ceremonies that mark the unofficial start of Christmas cheer. These free or low-cost events bring families, friends, and even strangers together for carols, hot cocoa, and that magical moment when a towering evergreen bursts into color. Here are some of the most anticipated active and upcoming ceremonies in and around Portland.
The crown jewel remains the Annual Tree Lighting at Pioneer Courthouse Square in downtown Portland. On Friday, November 28, starting around 5:30 p.m., thousands will pack “Portland’s living room” for a festive sing-along led by Thomas Lauderdale of Pink Martini fame, alongside local choruses and musicians. Santa himself flips the switch to illuminate a majestic 75-foot Douglas fir, donated by Stimson Lumber and adorned with colorful LED lights. This beloved tradition feels like the heartbeat of the city’s holiday spirit. Arrive early, bundle up, and join the crowd in belting out classics. It is free and family-friendly. More info here: https://www.travelportland.com/event/1486667/ or https://www.thesquarepdx.org/events.
Just northeast of the city center, The Grotto’s Christmas Festival of Lights kicks off on Friday, November 28, and runs nightly (except Christmas Day) through December 30. The opening night features the grand illumination of over a million lights across the serene gardens and cliffs, though the festival offers ongoing illumination and events rather than a single tree moment. Visitors wander paths lined with dazzling displays, enjoy indoor choral concerts in the chapel, outdoor caroling, puppet shows, and a petting zoo. Admission is modestly priced with online discounts. Official site: https://thegrotto.org/christmas/.
In the suburbs, several neighborhoods host their own charming events. Hillsboro’s Holly Days Celebration already lit up downtown on Saturday, November 22, with the main tree ceremony at 6 p.m., surrounded by artisan markets and performances. Details at: https://www.downtownhillsboro.org/holly-days-celebration/.
Coming up next: Lake Oswego’s 61st Annual Tree Lighting Festival on Friday, November 28, from 3-7 p.m. at Millennium Plaza Park, featuring music, a holiday market, Santa, and the big lighting at 5:30 p.m. Info here: https://www.ci.oswego.or.us/parksrec/61st-annual-tree-lighting-festival.
Beaverton Winter Lights and Tree Lighting takes place Friday, December 5, starting at 6 p.m. in Beaverton City Park, with performances, vendors, and the tree illumination around 7 p.m. Check the city’s page: https://www.beavertonoregon.gov/502/Beaverton-Winter-Lights.
Nearby, Bethany Village Tree Lighting and Holiday Market is set for Tuesday, December 2, from 4-8 p.m., with the lighting at 5:30 p.m., local student performances, Santa photos, and vendors. More at: https://www.bethanyvillage.com/tree-lighting/.
These ceremonies remind us why Portland shines brightest in winter. They are more than photo ops; they are chances to pause, sing off-key with neighbors, and feel the warmth of community amid the chill. Whether you head downtown or to a nearby suburb, grab a scarf and go. The lights are calling. Happy holidays, Portland. May your days be merry and bright.
