The Best Holiday Shows in Portland This Season

Drag queens, Nutcrackers, Kwanzaa performances, and more

By Conner Reed

Ginger Minj's Winter Wonderland, featuring the Drag Race All Stars runner-up, comes to the Aladdin on December 9

You've chosen your holiday lights display. You've gotten a grip on your shopping. Maybe you've even popped in to a holiday market or two, we won't tell. Now it's time to book some tickets, kick back, and absorb a healthy dose of holiday entertainment. From nutcrackers to drag queens to a pair of 1940s classics, these are the best holiday shows on offer in Portland this season. 

Remember the Night 

2 p.m. Sat–Sun, Dec 4–5, Hollywood Theatre, $7  

The Hollywood Theatre will kick off its December programming with this 1940 blast of Preston Sturges charm (the final film he wrote but did not direct). Barbara Stanwyck is a shoplifter whose trial runs through Christmas, Fred MacMurray her sympathetic DA, and the rest is screwball yuletide magic, perfect for a full-family matinee.  

Ginger Minj’s Winter Wonderland 

7 p.m. Thu, Dec 9, Aladdin Theater, $30 

The Drag Race All Stars runner-up (who does a hell of a Tammy Faye Bakker—look out Jessica Chastain) teams up with longtime friend Gidget Galore for a spirit-lifting nondenominational variety show inspired by the blissed-out technicolor spectacles of Andy Williams. Expect cheeky twists on classic carols, magic tricks, videos, dreidels, and more. 


8 p.m. Fri–Sat, 3 p.m. Sun, Dec 10–12, Newmark Theatre, $19–56  

The Portland Gay Men’s Chorus returns to live performance with this winter concert at the Newmark. Expect holiday tunes, less-specific winter fare, and—as always—gorgeous choral harmonies from one of the city's most delightful vocal ensembles. We would be remiss if we did not note that the poster for this event consists of four penguins and a few stripes of the trans flag, confirming the flightless birds as nature's most LGBT animals.

The Nutcracker 

Various dates & times Dec 11–26, Keller Auditorium, $24–156 

You know it, you love it, you’ve probably been seeing it since you were six—no reason to stop now. The Oregon Ballet Theatre continues their 2021/22 season with this sturdy holiday favorite after cancelling it last year for the first time since the company formed in 1989. Welcome back, Rat King, and may your rein be prosperous. (I haven't seen The Nutcracker for a while.)

It’s a Wonderful Life in Concert 

7:30 p.m. Mon, Dec 13, Arlene Schnitzer Concert Hall, $29–99  

The Oregon Symphony will screen Frank Capra's ever-enchanting 1946 fable about guardian angels and American greed(?) at the Schnitz, with its musicians providing live accompaniment. The classic score is by Dimitri Tiomkin, a Russian composer whom Capra hired for his first job in 1937, and who later went on to compose themes for 108 films, including Giant, High Noon, and Dial M for Murder.

Kwanzaa on Killingsworth 

Noon–5 p.m. Sun, Dec 19, 14 NE Killingsworth St, FREE 

Local composer Darrell Grant began the Soul Restoration Project, an initiative that investigates how “art can activate and renew our civic space,” over the summer—Kwanzaa on Killingsworth is its latest output. The market-slash-cultural celebration will feature work from Black artists in a variety of mediums, plus performances from Brown Calculus, soul duo LaRhonda and Mark Steele, and a youth showcase from Friends of Noise 

The Return of the Jinkx & DeLa Holiday Show 

8 p.m. Thu, Dec 30, Newmark Theatre, $29–99 

Drag Race champion and Portland native Jinkx Monsoon recorded their randy, cynical holiday special for Hulu last December with fellow Drag Race contestant BenDeLaCreme. This year, the duo is taking their cheeky brand of holiday humor to the stage with new songs 

New Year’s Eve with Gladys Knight & the Oregon Symphony 

7:30 p.m. Fri, Dec 31, Arlene Schnitzer Concert Hall, $49–125 

No need to scramble for New Year's plans this year: simply welcome 2022 by watching the reigning empress of soul join the Oregon Symphony to croon a program of classics old and new. While in reality, you'll be able to attend this concert and be home with plenty of time to pop the champagne (and perhaps even sneak in a viewing of Phantom Thread, a canonical New Year's Eve movie), we can't help but wish Knight would be belting out "Midnight Train to Georgia" when the clock strikes twelve.