16 Ways to Keep Yourself (and Your Guests) Entertained This Winter

Our guide to Portland's best seasonal shows, winter sports, holiday lights, and after-hours fun

By Zach Dundas, Aaron Scott, Kelly Clarke, and Marty Patail December 1, 2014 Published in the December 2014 issue of Portland Monthly

Go Watch Art

You don’t have to be a fan of schmaltz fests to find shows to fill you with winter cheer. 


For the humbug in all of us: Writer David Sedaris’s wry, painfully funny catalog of holiday snark returns. Portland Center Stage

The Christmas Carol Dec 4–Dec 28

Last year, Portland Playhouse’s musical adaptation of the Dickens classic infused the staid tale with new warmth, earning the theater Drammys for best ensemble, director, and production. Portland Playhouse

Chamber Music Northwest Winter Festival Jan 27–Feb 1

Brush up on your Beethoven and school yourself in Schubert with world-class musicians, as CMNW returns for the second annual winter fest—this time with a focus on “masterpieces.” Various venues, 503-294-6400

Italian Style: Fashion Since 1945 Feb 7–May 3

Gucci, Armani, Prada, Versace. You know their names; now learn their stories in the only West Coast stop for this exhibition of some 100 couture ensembles, which includes threads from Reed alum (’37) Emilio Pucci. Portland Art Museum

Cinderella Squared

Better get yourself two new ball gowns; February brings two very different takes on the greatest makeover of all time. First, the touring Broadway revival dresses up the Rodgers and Hammerstein classic with contemporary flair. Then, Oregon Ballet Theatre stages the popular Ben Stevenson ballet with music by Sergei Prokofiev. Broadway Across America’s Rodgers and Hammerstein’s Cinderella, Feb 17–22, Keller Auditorium. Oregon Ballet Theatre’s Cinderella, Feb 28–Mar 7, Keller Auditorium

Ride the Nostalgic Rails

Maybe you’ve got a train kid. You know the Thomas pantheon by sight and spend hours explaining light-rail engineering. Or maybe you’re a graduated train kid yourself, prone to reveries about the glories of a rail-bound, TSA-free past. Either way, the Oregon Rail Heritage Foundation’s annual slate of Holiday Express train rides has the low-key evening jaunt for you. Relax in vintage passenger cars the nonprofit lovingly preserves, pulled by a thundering diesel locomotive. Darkened woods roll past. Santa often strolls the aisles. No, you’re not really going anywhere—except, briefly, a happy place.

Cheer on your Winterhawks

Nostalgic for sports? (And we mean sports—not Jumbotron-addled, $10-beer, Maybach-driving SportsCenter fodder.) Grab seats for the Winterhawks, and embrace a humbler, rowdier era, when the sponsor was the local tire company and visiting players just got off the bus from Moose Jaw. At Winterhawks games, they play AC/DC songs. Diehard fans sport team gear (and team tats) they’ve probably owned since the ’80s. The players—all junior-hockey prospects with major-league hopes, some as young as 16—smash each other. Hard. And unlike some local teams we could mention, the ’Hawks have a fresh (2013) league championship in their trophy case.

Sing your heart out with a bunch of strangers

One second you’re drinking a beer; the next you’re holding a songbook and belting out Kelis’s “Milkshake,” shoulder to shoulder with an ad hoc choir of strangers. Just follow the off-key trills that emanate from the back room of Southeast Portland’s Crush Bar the last Friday of every month, where A People’s Choir holds its giddy-making meet-ups. Think of it as karaoke for wimps, or a dance party for shower singers; either way, the impromptu bar sing-alongs spark goodwill and camaraderie. Organizers choose a new theme each month—from divas to new beginnings to animals. If you want to sing out, sing out. A special holiday edition of A People’s Choir takes place on Dec 19 at Crush Bar

Just pretend it's still summer

Tired of cowering under that gray dome? Then rise and reclaim the summer! Prep for the blistering (imaginary) heat with a base tan from Organic Bronze Bar, a waterfront spot that’ll airbrush you with nonstreaking spray that boasts SPF protection on the slim chance you actually do make contact with a stray sunbeam. Next, amp up at the Celilo Natural Health Center’s B12 Happy Hour (4–6 pm Wednesdays), where staffers will literally inject you with a shot of “liquid sunshine”—a.k.a. an invigorating cocktail of mood- and immune-boosting vitamins. Then, wade into the crashing surf at North Clackamas Aquatic Park’s roomy wave pool and careen down the Milwaukie complex’s trio of big waterslides. Decompress with a potent potable at balmy Northeast tiki haven Hale Pele (above). If the hi-fi recordings of tropical rain don’t wash away your chilly mood, a couple of flaming rum Volcano Bowls will. Cap off your sunny sojourn by roasting your own s’mores over a personal (tabletop) campfire at Southeast bar White Owl Social Club

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