A December Jingle Ride in Boston
Braving the cold for the season of joy
By Tim Wilson
You may not think of December as cycling season but here in Boston we have an annual ride that always b-r-rightens the season of joy.
The Jingle Ride traditionally takes place on the second or third Sunday in December. The brainchild of bicycle Tour company Ciclismo Classico, for 28 years it has attracted bicyclists clad in holiday outfits from Santa to elves to reindeer to gingerbread men on an 18-mile loop. Starting in Arlington, Mass., it travels through Cambridge and Boston and back with multiple stops for caroling and an uber boom box in tow belting out holiday tunes.
This year more than 200 people pedaled the Jingle Ride on bicycles decked out with bells, lights, ornaments, wreaths, tinsel and even a chimney on the back of the “sweep” rider’s bike. Temperatures were in the low 30s when the Jingle Ride rolled out but as always, it did not fail to warm hearts. Exhibit A is the reception Jingle Riders receive from not all, but the vast majority of drivers.
Moving 200-plus riders in all manner of bicycles and levels of experience through busy city intersections can take a little time. Thankfully, most motorists are smiling and consumed with chuckles when Elf rides past followed by six Santas and a Rudolph complete with red nose accompanied by a chorus of colorful cyclists singing “Jingle Bells.”
For the riders, the fun of the day includes being the subject of dozens of amateur paparazzi as bystanders in downtown Boston pull out their phones to capture photos and video of the unexpected outbreak of holiday cheer on two wheels.
We have the better part of a year until the Jingle Ride comes around again. Until then, I encourage all of us to embrace the spirt of the ride as we roll through 2025.
About the author: Tim Wilson is a lifelong resident of Massachusetts. He is passionate about his family, Marquette University, bicycling and all Boston sports.