Christmas Portland

9 Delightful Ways to Be Festive During the Holiday Season in Portland

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‘Tis the season to browse pop-up markets for presents, sip cocoa under twinkling lights, and dance the night away with a crowd of Santas. There’s plenty to keep you in a festive mood all December long in Portland.

1. Find Your Perfect Christmas Tree (mid-November to mid-December)

Cost: Free to go to the farms (price of trees varies)

The Pacific Northwest is the home of Christmas Trees, and several U-cut farms are available in town. Christmas tree season starts in mid-November and farms close early if the trees run out (due to weather conditions and high demand, many farms are sold out by early December). A brutally hot and dry summer in 2021 and 2022 has been especially devastating, and many farms are open for one weekend only in November.

2. Cheer on the Carolers at the Great Figgy Pudding Caroling Competition (December 9)

Cost: Free

Set in and around Pioneer Courthouse Square in downtown Portland, the Great Figgy Pudding Caroling Competition is a free and festive event that allows the audience to decide on who the “best” caroling group is. It is a delight to stroll along and listen to Dickens carolers (dressed in Victorian garb) sing Christmas classics and a pirate-themed group (the PDXYar) belt out shantys. The event takes place rain-or-shine from 5:30-7:30pm (which also makes it the perfect opportunity to make a day of it downtown and shop for presents or grab a bite to eat).

3. Buy Presents From Local Makers and Artisans

Cost: Free

Portland is full of creative folk and December is the perfect time to snap up quality handmade and small batch items.

  • PDX Pop-Up Shops (Nov. 30-Dec. 31): Local designers and artists are given space in vacant storefronts in downtown Portland during the holiday season. Some of these pop-up shops later go on to become their own brick-and-mortar businesses. 2022’s pop-ups include bottles from urban wineries, the Oregon Potters Association, and NW travel inspired gifts. Take advantage of free Sunday parking at downtown Smartparks (the city run parking garages) during the holiday season.
  • Portland Saturday Market (Sundays through December 18th): A weekly market on the Waterfront (2 SW Naito Parkway), which is the largest continuously operating open-air arts and crafts market in the country (since 1974!). This Portland institution is a favorite place to buy local arts and crafts, including during the holidays.
  • ScanFair (December 10-11): This free event provides Portlanders with a taste of the Nordic with traditional food vendors and crafts. Historically it took place at Nordic House (8800 SW Oleson Road), a wood building in a modern Scandinavian design that holds the nonprofit Nordic Northwest. In 2022, it is taking place at the Oregon Convention Center (certainly a less charming, if larger, venue). Can’t get enough of hygge Scandinavian events? Nordic House has a range of holiday events, from a Julbord holiday dinner to dala horse Christmas ornament carving.
  • Portland Night Market (December 3-5): A quarterly event with food, music, drinks, photo ops, and vendors, you can enjoy a full night of fun and shopping (100 SE Alder St). While the main nights are free, a limited ticketed preview is available for a price on Thursday night ($23 – includes a free canned cocktail).
  • Woodworker Holiday Market (December 3): A celebration of wood and all it can make (from toys to jewelry to sunglasses) at Baerlic Brewing Company (2235 SE 11th Ave). Buy quality local products and grab a pint of barrel-aged beer.
  • Unique Markets Pop-Up (December 4-5): A new pop-up event at the Veterans Memorial Coliseum, attendees can enjoy 140 vendors as well as freed mulled or sparkling wine, a DIY gift wrapping station, and photo booths.
  • Crafty Wonderland Holiday Art + Craft Market (December 9-11): This biannual arts and crafts market at the Oregon Convention Center boasts hundreds of vendors. Historically it’s been a free event, but a small ($4) fee is being charged this year in order to cover the costs of COVID safety protocols. An exclusive pre-show is also available for $23 (which includes a free drink ticket).
  • Portland Bazaar (December 10-11, 17-18): Held over two weekends, this market features over 100 vendors in NW Portland at the Gear & Machine Works building (1715 NW 17th Ave).

4. Get in the Spirit with the Holiday Display at the Historic Pittock Mansion (November 21-January 4)

Cost: Adults: $15.50/Seniors: $13.50/Youth: $11.50/Under 6: Free

Built in the early 20th century to mimic a French Rennaissance-style chateau, Pittock Mansion rests atop the West Hills. On a clear day you can enjoy a panoramic view of Mount Hood, Mount St. Helens Mount Adams, Mount Rainier, and Mount Jefferson. A tourist attraction any time of year with its grand architecture and stunning views, Pittock Mansion dresses itself up with a festive holiday display in December. In 2022, the theme is “Music Makes the Season.” Be sure to buy tickets online in advance, otherwise they may sell out.

Local Tip: Pittock Mansion can be accessed via the Wildwood Trail in Forest Park. Get your daily walk and holiday festivities in one event! My favorite route is from Lower Macleay Park Trailhead, which is near NW 23rd (a popular shopping street). It’s a 5.7 mile round trip hike and it gets pretty steep in parts. If you hike it in December, it may be muddy as well because of the rainy season. If you want a little bit shorter route (which unfortunately does not cut out the steepest bits), you can start at the Upper Macleay trailhead for a 2.7 mile roundtrip.

5. Watch a Holiday Performance

Cost: Varies

December is the time to be transported to another world with Christmas classics like The Nutcracker or A Christmas Carol.

  • The Nutcracker with the Oregon Ballet Theatre (December 10-24): The story of Clara and her nutckracker-turned-prince is one of the most popular ballets in the world and a Christmas tradition. Tickets start at $29 and many shows are accompanied by a live orchestra (what better way to hear “Dance of the Sugar Plum Fairy”?).
  • The Christmas Carol: Portland Playhouse, an intimate theater in an old church, puts on a performance of Dickens’ holiday classic that includes Christmas carols (Nov. 25-Dec. 30, tickets start at $32.50).
  • Musical Panto (December 10-18): While panto is not strictly holiday-related, the Portland Panto Players put on a family-friendly event every December based on a beloved children’s story (tickets start at $19). Past years have included Alice in Wonderland and The Wizard of Oz, and 2022 brings Peter Pan. Panto is an interactive theater experience, which is delightful for everyone and keeps children engaged.
  • It’s a Tony Starlight Christmas (December 11): A throwback to a 1950s-style revue, this show has a mixture of musical acts, Bing Crosby impressions, and comedy routines (tickets start at $30). I caught a show in 2018, and while I was too young to appreciate all the jokes and impressions, it was an energetic and entertaining show.
  • Elf in Concert (December 17): Watch a showing of the feature film, accompanied by the Oregon Symphony (tickets start at $29).

6. Ride the Holiday Express (November 24-December 19)

Cost: Adults: $25/Kids: $20

Take a short (40-45 min) trip in vintage rail cars decked out with garlands and lights from Oaks Park Amusement Park through the Oaks Bottom Wildlife Refuge. Santa and his elves are also catching a ride onboard. Don’t be late – the trains leave on time.

Local Tip: If you can’t get enough of trains, get a hot tea at Tea Chai Te in Sellwood afterwards. It’s built into an old caboose, and you can sit in the caboose or below in the atrium.

Mukilteoedits (Wikipedia)

7. See the Night Lit Up with Holiday Lights

Cost: Varies

Holiday light displays are out in full force to make the season bright throughout the month.

  • Zoolights (November 19-January 1): With animal-themed light displays with over a million lights (but sadly, no real animals visible), Zoolights is a favorite with families (tickets starting at $16). On select nights, you can drive through the lights ($65/vehicle).
  • Winter Wonderland at the Portland International Raceway (November 26-January 1): A drive-through event (except for special * nights), this is the “Largest Holiday Light Show West of the Mississippi” with over 250 light set pieces, including fully animated scenes (car: $35/RV: $75).
  • Christmas Festival of Lights at the Grotto (November 26-January 2): The largest Christmas choral festival in the world, with five different choir performances occurring throughout the night. There’s also a puppet show, a petting zoo (cancelled for 2021), and peaceful grounds decked out with light displays (tickets are $16 for adults/$8 for kids at the gate).
  • Peacock Lane (December 15-31): The houses on this SE Portland street put on a free light display with themes from Santa Claus to Star Wars. Because of its accessibility and affordability, Peacock Lane gets busy. My favorite is going on a Pedestrians-Only night (NOTE: these will not be held in 2021) when it’s drizzling. Despite it being Portland, the city of rain, precipitation helps keep the crowds away.
  • Christmas Ships Parade (select lights from December 3-21): Head to the waterfront around 7pm to watch proud boat owners who’ve decked out their crafts with festive lights. For a view of the marine parade from the water, you can take the Christmas Ship Dinner Cruise on the Portland Spirit (adult: $86/child: $43).

8. Listen to the Sounds of the Season with Christmas Concerts

I have a strict No-Christmas-Music-Until-After-Thanksgiving policy, much to my husband’s dismay (he is one of those folks who would turn it on as soon as the last piece of Halloween candy was passed out). But once leftover turkey sandwiches give way to Advent Calendar chocolate, I’m all in on the music. No matter what kind of Christmas music gets you in the spirit – gospel, Celtic, classical – there is a concert in Portland for you.

9. Party with Santa at Stumptown Santacon (December 18th)

Cost: $23

A themed bar crawl and outdoor dance party from 4pm-10pm (the dance party starts at 6pm), costumes are mandatory at Stumptown Santacon. If you don’t want to dress like Old Saint Nick, you can put on an ugly Christmas sweater, a santa hat, reindeer antlers, or whatever festive costume inspires you to drink and dance the night away, Christmas style. And this event truly captures the holiday spirit – part of the proceeds are donated to local charities.

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