Events
In downtown Portland, OR.
Shop Small. Shop Portland!
Thursday November 6th
Small Shops Big Hearts helps you be intentional about how and where you spend your money. We make it easy for you to find businesses owned and operated by people who live in our communities and care about the neighborhoods where they operate and the people who live, work and play close by. Discover the small shops of Portland.
10:00 AM - 10:00 PM
Stimson Lumber Tree Arrival
Wednesday November 12th
Kick-off of the holiday season Downtown as Portland’s 75ft tall Douglas-fir Tree is welcomed to Portland’s Living Room, Pioneer Square. Say hello to Santa, enjoy free hot chocolate and join in the fun of this annual tradition.
11:00 AM - 12:30 PM
41st Annual Tree Lighting Ceremony at the Square
Friday November 28th
A joyful community sing-along led by Portland’s own Thomas Lauderdale of Pink Martini with many of Portland’s finest musical artists and chorale singers. Portland’s Tree Lighting Ceremony is the highlight of the holiday season in downtown. Join in this holiday tradition as Santa Claus ‘flips the switch’ to illuminate nearly 10,000 colorful lights on our City’s Tree that will shine bright throughout the holiday season. Presented by SmartPark.
05:30 PM - 06:45 PM
Portland Holiday Brew Fest
Friday December 5th
The Portland Holiday Brew Fest returns on December 5th & 6th, bringing winter cheer and delicious beer to The Square! Join us under covered, heated tents to enjoy 30+ holiday/winter beers & ciders from around the Northwest, plus music from vinyl DJs and a variety of cozy winter foods.https://www.pdxholidaybrewfest.com/
05:30 PM - 10:00 PM
11th Annual Great Figgy Pudding Caroling Competition
Friday December 12th
The 11th Annual Great Figgy Pudding Caroling Competition, hosted by KGW’s Drew Carney, is a fun, festive, and joyful competition bringing hundreds of carolers to a ten-block radius the surrounds Portland’s Living Room®. Carolers perform in front of Downtown’s favorite nearby shops, restaurants, and hotels with the top three caroling groups holding a “carol-off” at The Square. Members of the public can participate in this FREE event by registering to perform with a caroling group or by visiting performing caroling groups to vote for your favorite.
06:00 PM - 08:00 PM
34th Annual Tuba Christmas Concert
Saturday December 13th
This iconic, quirky and heart-warming holiday musical tradition is back! Experience the mighty sounds of big brass as nearly 300 tubas play in harmony while the crowd is invited to sing along. This live performance is one of the largest in the country with tuba participants travelling from all points of Oregon to join in this festive event with a crowd of thousands. Attending this seasonal performance is FREE for the public.
01:30 PM - 03:00 PM
Portland’s Public Menorah at The Square
Sunday December 14th
Chabad of Oregon invites the community to celebrate Hanukkah with the annual lighting of Portland’s Public Menorah at Pioneer Courthouse Square, Sunday, December 14 – Sunday, December 21, 2025. First Night Celebration – Sunday, December 14 at 4:00 PM Live music, traditional Chanukah foods, dignitaries, and family festivities will launch eight nights of light and joy. The menorah will be lit at 5:30 PM. Lighting Schedule: Sunday, December 14 – Festivities begin at 4:00 PM Monday, December 15 – Thursday, December 18 – 5:30 PM Friday, December 19 – 3:00 PM Saturday, December 20 – 6:30 PM Sunday, December 21 – 5:30 PM