Celebrate the Holidays in Portland

Celebrate the holidays with a vacation to Portland! Whether you’re visiting in October, November, or December, there are plenty of events to help get you in the spooky, thankful or festive holiday spirit. Enjoy ghost tours and pumpkin-themed festivals during October, holiday lights and farmers markets during November, and holiday shopping and New Year’s Eve celebrations during December. Portland really does have something for everyone!

October Events 

West Coast Giant Pumpkin Regatta (October 15 & 16) 

One of the most unique fall festivals in Oregon, the West Coast Giant Pumpkin Regatta, is a can’t-miss event! Join people from all over the country to cheer on costumed characters paddling giant pumpkins in a series of races. The weekend kicks off with Pumpkins and Pints and the giant pumpkin weigh-off followed by the regatta on October 16. 

The Spirit of Halloweentown (September 17 – October 31)

If you grew up watching Halloweentown then The Spirit of Halloweentown is for you! The event takes place in St. Helens (30 miles from the hotel) where the movie was filmed. Each year, St. Helens transforms into a spooky season haven complete with costume contests, trick-or-treating, haunted tours, a scarecrow contest, and more. The celebration even kicks off with the lighting of the Great Pumpkin. 

Portland Ghost Tours (dates vary depending on tour)

Scare yourself silly with a haunted ghost tour of our beloved city. Explore the most haunted places in downtown on The Ghosts of Downtown Portland tour (September 16 – November 10), indulge in a beer while discovering the Shanghai Tunnels with the BeerQuest Haunted Pub Tour (September 23 – December 31), and seek out less than peaceful spirits during A Night with Ghosts (September 16 – October 31). 

November Events 

Holiday Lights (dates vary depending on event)

Get in the holiday spirit with light shows and festivals. Head to The Grotto where, starting the day after Thanksgiving, you can enjoy the Christmas Festival of Lights. The event features outdoor caroling, puppet shows, musical guests, and plenty of lights. Head over to the Oregon Zoo for the annual Zoo Lights display (November 21 – January 5) or, for a more adult atmosphere, enjoy BrewLights (November 18 – 19). The grown-up spin on Zoo Lights includes access to the festive light displays and samples from local breweries. 

Farmers Markets (dates vary depending on event)

Take advantage of the harvest season by attending our iconic farmers markets. Enjoy delicious bites from the Portland Farmers Market at PSU (Saturdays January 22 – December 17) which boasts almost 150 farmer and vendor stands. Get your holiday shopping started at the Woodstock Harvest Market (November 20) which is known not only for its fresh produce and baked goods, but also for its jewelry, ceramics, and art. 

December Events 

Christmas Ship Parade (December 2 – 21)

You don’t want to miss the Christmas Ship Parade featuring brightly decorated boats parading along the Willamette and Columbia Rivers. Enjoy the light displays which can be seen from bank to bank on the rivers. 

Holiday Shopping (dates vary depending on event)

Portland offers tons of opportunities to shop for everyone on your list this holiday season! Stop by Crafty Wonderland (December 9 – 11) the city’s largest arts and crafts market hosting more than 250 vendors, browse the PDX Pop-Up Shops (November 16 – December 31) which uses vacant storefronts to showcase local designers and artists, and cruise through the Portland Bazaar (December 10 – 11) to support small business. 

New Year’s Eve Party Cruise (December 31)

Celebrate 2023 with a Prohibition-style party! The On the Boardwalk party cruise will take place aboard Columbia Gorge Sternwheeler featuring two decks, a lively DJ, three complimentary drinks, appetizers, and more. Don your best suits and flapper dress and ring in 2023 in style! 

Stay at Hotel Zags 

Your visit to Portland isn’t complete without staying at Hotel Zags. Our convenient downtown location is close to everywhere you want to be while our newly revamped rooms and suites offer pillow-top beds, earth-friendly bath products, and gorgeous views. Explore our Special Offers to make your holidays in Portland even more festive!