Here, we highlight the city’s most popular — and uniquely Portland — events so you don’t miss a tuba-tooted beat. The annual Tree Lighting Ceremony, a caroling contest throw-down, a beer festival and of course a concert played by 300 tubas: Pioneer Courthouse Square is the center of Downtown Portland’s holiday entertainment.
With so much going on, it can be easy to miss activities, performances and cultural traditions that call downtown Portland home. Don’t worry, we got your back.
Pioneer Courthouse Square’s Holiday Events
In celebration of its 35th holiday season, Pioneer Courthouse Square will host and produce over 37 free, family-friendly holiday events, activities, performances and beloved community traditions. The Square will kick off the downtown holiday season with the Stimson Lumber Tree Arrival on Friday, Nov. 15 at noon. Santa Claus will help bring the city’s 75-foot-tall (23 m) Douglas fir tree down Southwest Sixth Avenue and into Portland’s “living room.”
The 35th Annual Tree Lighting Ceremony, presented by SmartPark, will once again be held the day after Thanksgiving- Friday, Nov. 29 at 5:30pm. A crowd of over 25,000 Portlanders will unite in a joyful and festive sing-along led by Thomas Lauderdale, members of Pink Martini and a diverse array of our city’s talented musicians and chorale singers. The evening’s program will feature Mayor Wheeler, city dignitaries and Santa Claus as they ‘flip the switch’ and illuminate 14,000 colorful lights on our city’s centerpiece of the holiday season.
The holiday season continues with The Great Figgy Pudding Caroling Competition, presented by Portland Mall Management, Inc. This fun and festive event brings caroling groups of all ages to the heart of downtown as they perform along the Portland transit mall beginning at 6:00pm on Friday, Dec. 13. The top three caroling groups will then hold a “carol-off” at the Square where the grand prize winner will be selected by crowd applause and awarded $1,000.
The 29th Annual Tuba Christmas Concert, presented by SmartPark, will bring the sound of nearly 300 tubas to the heart of downtown on Saturday, December 14th at 1:30 p.m. This free community performance will feature the booming brass sound of nearly 300 tubas as they play festive songs with the help of singers from the Portland Opera.
Pioneer Courthouse Square will carry on the tradition of involving local schools, bands, and groups in the holiday season with festive performances in the Square and surrounding adjacent blocks throughout December. In addition, Holidays on the Mall, a free pop-up event series will bring tasty treats, performances and seasonal giveaways to select locations along Portland’s transit mall.
Holiday Ale Festival
Held in the heart of Downtown Portland, the Holiday Ale Festival returns Dec. 4–8 and keeps attendees warm and dry under a large clear top tent that covers Pioneer Courthouse Square while allowing for views of the city lights.
Gas heaters create a cozy ambiance under the boughs of one of the region’s largest decorated Christmas trees. More than 50 breweries are featured at this year’s event, all of which are bringing beers created to bring joy to all the beer fans. These aren’t beers you’ll find in the supermarket — the brewers have put together special recipes, collaborations and blends just for their fans, and will release them at the Holiday Ale Festival. From Belgians to barrel-aged creations, ciders, IPAs, hazy beers, stouts and sours, these beers are often the result of long-term planning and showcase the creative prowess of the brewers, which means you are assured to get something new and exciting to try!
More Holiday Fun Near the Square
Don’t miss these other holiday events and offerings in Downtown Portland this holiday season.
Free Parking Sundays
This year, shoppers will receive a special gift: Free parking in SmartPark garages all day on Sunday, Dec. 8, 15 and 22. Between noon and 5 p.m., show your parking ticket at the PDX Pop-Up Shop in Pioneer Place located at 700 SW Fifth Ave. on the lower level next to the Gap, or at Boys Fort located at 1001 SW Morrison St. Eligible drivers will receive a $5 parking voucher to cover the day’s cost of parking in SmartPark garages.
This year, Santa is traveling from the North Pole and making several stops in Downtown Portland. At Pioneer Place, Santa arrives on Thursday, Nov. 14, and dons his hipster threads on Dec. 7, 8, 9 and 19. Make sure your furry friends get a picture with Hipster Santa on the evening of Dec. 9.
Santa is also making a special stop by Nordstrom on Friday, Nov. 29 for the Tree Lighting Ceremony at the Square, and for a breakfast event on Thursday, Dec. 7 from 9:30 a.m.–1:30 p.m. Kids can tell him their Christmas wishes from 11 a.m.–6 p.m. on Dec. 13–15, as well as Dec. 20–24. On Christmas Eve, Santa is only available until 4 p.m. before he begins his world-wide tour that evening.
Each year, Chabad of Oregon hosts a Chanukah Menorah Lighting at Director Park. Join the Festival of Lights celebration on the first night of Chanukah with music, traditional foods, children’s crafts and a Menorah Lighting with dignitaries on Sunday, Dec. 22 from 4–6 p.m. Menorah Lightings occur nightly through Monday, Dec. 30. This is the 36th year that Chabad of Oregon is lighting Portland’s Public Menorah.
Festival of the Last Minute
‘Tis the season for Portland Saturday Market’s Festival of the Last-Minute! Open daily beginning Thursday, Dec. 19 through Christmas Eve, the marketplace will once again feature one-of-a-kind handcrafted items, exotic foods and an appropriately chilly, yet perennially cool atmosphere. The event marks the perfect opportunity to shop the work of talented area artists and support the local economy, with 40 categories of arts and crafts. After all, just because you didn’t make the gifts yourself, doesn’t make them any less handmade or thoughtful.
Holiday Spirits Fest
Portland Saturday Market presents their Holiday Spirits Fest, returning Dec. 21 and 22. This annual celebration of spirits highlights local distillers who are shaking up Portland’s vibrant scene. It’s all about meeting the makers of the local crafted spirits and the wonderful concoctions people can create using local spirits. Each distiller will have a signature cocktails to tantalize your taste buds. Tastings are free, but you can purchase cocktails and bottles too. This is a free event, and you must be 21 years or older with ID to enter.
Neighborhood Maker Fest
Old Town Creatives presents a special pop-up art gallery and shopping event, Neighborhood Maker Fest, featuring artwork, unique apparel and other goods made by creatives that make the Old Town District a colorful and creative place. To join the event, head to 333 NW Fifth Ave. on Saturday, Dec. 7 from 11 a.m. to 5 p.m.
Portland is full of bright ways to embrace the shorter days of winter; here are some of the stars in the city’s constellation of holiday light displays.
The Holiday Ale Festival, set beneath the region’s largest decorated holiday tree, returns every year with more than 50 big, bold beers designed to keep revelers warm on cold winter nights.
Like an Advent calendar loaded with sugary treats, the days leading up to Christmas in Portland hold an abundance of sweet memories.