Know Before You Go
Editor’s Note: Check back in November 2020 for information about this year’s holiday season.
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
Celebrating nearly four decades of holiday cheer, Pioneer Courthouse Square hosts and produces dozens of free, family-friendly holiday events, activities, performances and beloved community traditions every year. The Square kicks off the downtown holiday season with the Stimson Lumber Tree Arrival in mid-November. Santa Claus helps bring the city’s 75-foot-tall (23 m) Douglas fir tree down Southwest Sixth Avenue and into Portland’s “living room.”
The Annual Tree Lighting Ceremony, presented by SmartPark, returns the night after Thanksgiving. A crowd of over 25,000 Portlanders unite in a joyful and festive sing-along, typically 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 features 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. The top three caroling groups then hold a “carol-off” at the Square where the grand prize winner is selected by crowd applause and awarded $1,000.
The Annual Tuba Christmas Concert, presented by SmartPark, brings the sound of nearly 300 tubas to the heart of downtown every December. This free community performance features 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 carries 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 brings 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 every December 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. Over 50 breweries are typically represented at the festival, pouring beers crafted to bring joy to all their fans. These aren’t beers you’ll find in the supermarket — the brewers put together special recipes, collaborations and blends just for their fans, and 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
In 2019, shoppers received a special gift: Free parking in SmartPark garages all day on Sunday, Dec. 8, 15 and 22. Between noon and 5 p.m., visitors could show their parking ticket at at Boys Fort located at 1001 SW Morrison St. Eligible drivers received a $5 parking voucher to cover the day’s cost of parking in SmartPark garages.
Every year, Santa travels from the North Pole and makes several stops in Downtown Portland. At Pioneer Place, Santa even dons hipster attire for a uniquely Portland photo opportunity. (Make sure your furry friends get a picture with Hipster Santa on pet-friendly days.)
Santa also makes a special stop at Nordstrom for the Tree Lighting Ceremony at the Square, and returns several times in December leading up to Christmas Eve (before he begins his world-wide tour that evening).
Each year, Chabad of Oregon hosts a Chanukah Menorah Lighting at Director Park. Visitors can join in the Festival of Lights celebration on the first night of Chanukah with music, traditional foods, children’s crafts, Chanukah treats and a Grand Menorah Lighting.
Menorah Lightings occur nightly through the end of Chanukah. In 2019, the Chabad of Oregon celebrated its 36th year of lighting Portland’s Public Menorah.
Festival of the Last Minute
Celebrate the season at Portland Saturday Market’s Festival of the Last-Minute! Open daily beginning in mid-December through Christmas Eve, the marketplace features 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 hosts their Holiday Spirits Fest every December. This annual celebration of spirits highlights local distillers who are shaking up Portland’s vibrant cocktail scene. It’s all about meeting the makers of these locally crafted spirits and the wonderful concoctions people can create using them. Each distiller has 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
In 2019, Old Town Creatives presented a special pop-up art gallery and shopping event, Neighborhood Maker Fest, featuring artwork, unique apparel and other goods made by the people who make Old Town such a colorful and creative place.
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.