10 Best Holiday Events and Attractions in Portland, Oregon

Portland, Oregon celebrates the holidays with an assortment of annual events across the city. We are not exaggerating when we suggest that there are all kinds of events. For example, where else besides Portland can you go on an annual holiday river cruise that is dedicated to Cinnamon Bear a character from a 1920's radio show? 

That's not the only one of a kind holiday event found in the city. There are lots more like the annual tree lighting in downtown Portland. Maybe that seems like an event you would find in any city, but in Portland they will have 200 tubas on hand to play Christmas carols or maybe they will have a guided sing along with the thousands of people that show up. 

Of course Portland cannot celebrate any season without getting the local brewers in on it, and they do this brilliantly at the Holiday Ale Festival in Pioneer Courthouse Square each year. 

Historic District


Of outstanding quality, this ballet company continues to rise to the expectations of critics throughout the region and the nation as well. From classics like Swan Lake and the company's yearly performance of The Nutcracker. No holiday season is...  Read More



A Portland holiday tradition, the Holiday Ale Festival is an outdoor annual event taking place November 30th through December 3rd from 11 am to 9:30 pm Wednesday through Saturday, and 11am to 5pm Sunday. Even though the temperatures may be on...  Read More

South Waterfront District


You and your child will be guests of honor on this two-hour cruise. Enjoy holiday treats including hot chocolate, while a cast of fanciful characters entertain you with storytelling, music and magic. There is a perfect mix of activities to...  Read More



Built for Henry and Georgiana Pittock (who lived in the house from 1914 to 1918), the Pittock Mansion is a stunning architectural specimen and a repository for elegant furnishings. Pittock Mansion has 22 rooms and the gardens outside having...  Read More



A must-visit if you're in Portland during the holiday season. The Festival of Lights at the Grotto is a spectacular event that features 150 indoor music concerts as well as dramatic living history enactments and holiday light displays that...  Read More

Pioneer Courthouse Square Tree Arrival


Join thousands of Portlanders in the heart of the city when the massive Christmas tree that dominates Pioneer Courthouse Square arrives. There's a special tree lighting ceremony held on the Friday after Thanksgiving, allowing you a chance to...  Read More



Going strong for over 60 years, this annual Christmas event features 55 - 60 ships of all sizes, 14 to 65 feet long, bedecked with sparkling holiday lights. Each night for two weeks, boat owners proudly cruise the Willamette and Columbia Rivers,...  Read More

Southeast Portland


The residents of Peacock Lane have been decorating their Tudor style homes for the holidays since the 1920's. Their legendary light displays continue each December from the 15th until the 31st from 6 - 11 PM. The residents will be serving free...  Read More

Winter Wonderland


The granddaddy of Portland holiday events is Winter Wonderland at the Portland International Raceway. Billed as the largest holiday light exhibit west of the Mississippi, this drive-through exhibit is truly huge, with glittering animated...  Read More

Zoolights Festival


Become a kid again when you visit Portland's Oregon Zoo during holiday time. The zoo comes to life with a million and a half twinkling lights and holiday decorations. Kids will enjoy a puppet show put on especially for them, and the whole family...  Read More


Meet Meagan Wristen

Meagan Wristen is an Oregon resident by choice and thinks Portland is a tremendous city that everyone should visit. Originally a Texas girl, she has lived all around the United States,...  More About Meagan