Annie Seo

In the winter, Pioneer Courthouse Square becomes an unholy vortex of bitter winds as sharp and cold as frozen daggers that ricochet off the surrounding buildings and swirl around the giant Christmas tree. It is hell and you should not go there.

Unless you love Christmas carols! I do not. However, I did recently venture into Portland’s frozen tundra of a living room for the Fourth Annual Great Figgy Pudding Caroling Competition. Upon arrival, I found a couple hundred revelers milling around the square. Small tents sold toys and chestnuts roasting on an open fire. (Note: I did not investigate the nuts/open fire logistics—sounded dangerous given the wind situation.)

The competition’s judges were the Dickens Carolers, a quartet sporting Victorian-era attire complete with top hats and bonnets. They took the stage and sang a festive number. It was pleasant, but not overly engaging—the two most critical components of successful caroling. Then the dozen or so competing groups broke off to perform on street corners around the square.

Already numb and seething, I followed the green glow of the Starbucks sign, waited in line for 20 minutes, and attempted to feel something by pumping my body full of peppermint mocha. This attempt was unsuccessful.

Nevertheless, I made my way to the nearest street corner to drink in the sounds of the Westside Singers, who were performing an eye contact-heavy version of “Holly Jolly Christmas.” When the judges departed to observe another group, I decided to follow and eavesdrop on their process, but they seemed to notice me loitering in their wake. Exposed, I was forced to stop trailing them.

My favorite group was the Portland Timbre, who changed the chorus of Toto’s “Africa” to “I had Christmas down in Africa.” I enjoyed this, probably because “Africa” is a righteous banger in any context. And then I stumbled upon PDXYar—a troupe of caroling pirates wearing heavy cloaks, furs, and tricorn hats. They yelled “HUZZAH,” dinged a loud bell, and sang about cannonballs and rum. If we’re judging on my personal caroling success scale, I’ll admit PDXYar didn’t rank high. But both the judges and the audience loved them, so they beat out the other two finalists for the $1,000 grand prize.

Caroling is a thankless sport—singing for heartless Grinches (like myself) while exposed to the elements must wear you down. Although I can’t support the intersection of pirate culture and Christmas, and although I would never be caught dead caroling myself, based on the impressive endurance and stamina required to partake in this yuletide activity, I’m giving it 10 out of 10 candy canes.


Overall Christmas rating: 10 candy canes.