Festive Fun

21 Portland Holiday Happenings for Maximum Seasonal Fun

The most wonderful time of the year is here and there’s so. Much. To. Do.

By Kayla Brock November 30, 2017

Nutcracker qggwbs

OBT's The Nutcracker returns along with lots of other holiday goodies. 

Image: James McGrew

Thanksgiving is done and digested (ish), which can mean only one thing: the holidays are rolling toward us apace, with trees to trim, Santas to spot, glad rags to don, and guilty pleasures aplenty to enjoy. Check out these 21 events through December to ramp up your holiday spirit, handily organized for whatever it is you need this year.

In search of: Santas (many, many Santas)

Stumptown Santa Con

4 p.m. Sat, Dec 16, Splash Bar, $10
This annual traveling costume party is back, with "Island of Misfit Toys" as this year’s theme. Kicking off at the Pearl District's Splash Bar, there are DJs, fire pits, and plenty of pit stops promised. Proceeds go to Portland Police Bureau’s Sunshine Division and Stumptown Events.

In search of: a holiday classic

The Nutcracker

Various times Dec 9–24, Keller Auditorium, $23–105
The Oregon Ballet Theatre brings back its annual performance of George Balanchine’s Christmas classic, featuring soloist Candace Bouchard taking on her favorite roles of Dew Drop and the Sugar Plum Fairy for the last time before retirement.

In search of: belly laughs

Twist Your Dickens

7:30 p.m. Tue–Sun, 2 p.m. Sat–Sun, noon Thu, Dec 5–31, Portland Center Stage, $25–52
Legendary comedy troupe Second City sends up Dickens’s A Christmas Carol, with audience participation and lots of improv. (Recommended for ages 14 and up.)

In search of: seasonal luminosity

Winter Wonderland

5:30–9:30 p.m. Sun–Thu, 5–11 p.m. Fri–Sat thru Dec 26, Portland International Raceway, $6–50
Claiming to be the “largest light show West of the Mississippi,” PIR's Winter Wonderland display celebrates 25 years this season. Marvel at more than 250 colorful light set pieces from the cozy confines of your car as you drive around the track. If you’d prefer to stretch your legs, check out the Lights and Leashes Dog Walk on Tuesday, December 5.


5–9 p.m. thru Jan 7, Oregon Zoo, FREE–$14.95
The one thing better than the zoo by day is the zoo by Christmas night. This tiny world in the West Hills is a spectacle of color and light over the festive season. If that’s not enough to lure you there, let us add two magical words: elephant ears. No wonder Santa makes an appearance here.

Peacock Lane

6–11 p.m. Dec 15–31, SE Peacock Lane, FREE
Stroll this neighborhood extravaganza sipping hot cocoa or cider and taking in the manic, monumental effort to outshine the house next door. Expect nativity scenes, moving parts, cartoon characters, and lots and lots of spectators.

In search of: holiday beverages

Holiday Ale Festival

11 a.m.–9:30 p.m. Wed–Sat, 11 a.m.–5 p.m. Sun, Nov 29–Dec 3, Pioneer Courthouse Square, $35–100
Beer lovers rejoice! More than 50 craft beers are wrapped into one winter event smack in the middle of the city. The five-day celebration showcases such local suds as Gigantic’s The Cat Ate My Stash and Pissed on The Christmas Tree IPA, Hopworks's Yule Only Live Once Imperial Dessert Beer, and Pelican Brewing’s Dark Hearted Blonde Pale Stout.

Gingerbread House Party

2 p.m. Sat–Sun, Dec 16–17, Hip Chicks Do Wine, $20
The Southeast urban winery offers two afternoons of gingerbread house decoration. Expect wine, beer, or hot cider, plus plenty of artisanal architecture. For the competitive builders among us, there will be a social media contest for a $25 gift certificate.

In search of: a reason to get fancy

Vespertine Ball

9 p.m.–2 a.m. Sat, Dec 9, Melody Ballroom, $40–45
Held in the Melody's Grand Ballroom, this masquerade ball is a snowy wonderland. Don a costume or formal attire, and expect gothic/industrial beats from Portland's DJ Carrion until the clock strikes midnight, when classical music kicks in for a traditional waltz.

In search of: a moment in nature

Christmas Tree Tour

Noon Sat, Dec 16, Hoyt Arboretum, $3 recommended
Join local conifer expert Ken Denniston for a guided tour of popular Christmas trees at the Hoyt Arboretum, including Oregon natives and other Christmas trees available in the Portland area. Learn Christmas tree history and tips on picking out the perfect specimen. 

In search of: last-minute gifts

Crafty Wonderland

11 a.m.–6 p.m. Sat–Sun, Dec 9–10, Oregon Convention Center, FREE
More than 250 vendors sell their wares—T-shirts, totes, jewelry, art, and more—at this annual gift bonanza.

Portland Night Market

4 p.m.–11 p.m. Fri–Sat, 11 a.m.–4 p.m. Sun, Dec 1–3, 100 SE Alder St, FREE
Enjoy the last of these indoor Portland markets until next spring, with more than 100 vendors to choose from. Take in free samples of beer, cider, cheese, and chocolate as you rummage through the stalls for gifts.

Give Good Gift

5–9 p.m. Fri, 10 a.m.–3 p.m. Sat, Dec 1–2, 525 SE Pine St, FREE
Returning to Union/Pine, the two-day holiday pop-up features such local brands as Bridge & Burn, Bee Local, Goodwell, and Altar.

America's Largest Christmas Bazaar

10 a.m.–6 p.m. Fri–Sat, 10 a.m.–5 p.m. Sun, Dec 1–3, Portland Expo Center, FREE–$8
This “craft-based event” promises products including pet paraphernalia, journals made from vintage children’s books, fudge, handmade baby quilts, handmade personalized ornaments, flavored soap, log furniture, and, yes, even more.

In search of: Christmas music

27th Annual Tuba Christmas Concert

1:30–3 p.m. Sat, Dec 9, Pioneer Courthouse Square, FREE
Hark as 300 tubas blast the joys of the season through downtown Portland.

The Grotto's Christmas Festival of Lights

5–9:30 p.m. daily thru Dec 30, 8840 NE Skidmore St, FREE–$11
Featuring nearly 160 indoor holiday concerts, the Grotto proudly calls this the largest Christmas choral festival in the world. Sit inside the 600-seat chapel, known for its acoustic vibrations, and enjoy outdoor activities such as caroling, puppet shows, and a petting zoo.

Portland's Singing Christmas Singing Tree

7:30 p.m Thu, 7:30 p.m. Fri, 2 and 7 p.m. Sat, noon Sun, Nov 30–Dec 3, Keller Auditorium, $20–60
This two-hour holiday concert returns for the 55th year, with more than 350 adult and youth choir members and a few numbers from the Jefferson Dancers.

Gospel Christmas with the Oregon Symphony

7:30 p.m. Fri–Sat, 4 p.m. Sun, Dec 8–10, Arlene Schnitzer Concert Hall, $35–115
Conductor Charles Floyd leads the Northwest Community Gospel Choir and Oregon Symphony for a performance of soulful gospel music.    

Holidays on the Mall—The Dickens Carolers

5:30–6:30 p.m. Fri, Dec 15, downtown Portland, FREE
Clad in traditional Old English costumes, a capella carolers will stroll down Southewest Morrison and Yamhill Streets and 5th and 6th Avenues heralding ye olde Yuletide season.

In search of: a night at the theater

A Christmas Memory/Winter Song

7:30 p.m. Tue–Sat, 2 and 7:30 p.m. Sat–Sun, noon Thu thru Dec 31, Gerding Theater, $25–60
It’s fruitcake weather, so Truman Capote’s classic tale seems an apt addition to the holiday calendar. Portland Center Stage pairs it with a cycle of seasonal songs created by Merideth Kay Clark (a.k.a. Elphaba in the first touring production of Wicked) and PCS production associate Brandon Woolley.

A Christmas Carol: A One-Man Ghost Story

7:30 p.m. Wed–Sat, Dec 20–23, Theatre Vertigo, $10–20
Phillip J. Berns’s one-man telling of Charles Dickens's A Christmas Carol returns, with music by Christopher Beatty. Tiny Tim never gets old.

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