27th Annual Ciclismo Classico Jingle Ride

Check out our favorite photos from past Jingle Rides!

Started in 1996, the Jingle Ride is a leisurely 18.5-mile ride and festive bike parade from Arlington to Boston and back. Now in its 27th year, the Jingle Ride is one of the longest-running Boston holiday sporting events and certainly one of the most colorful. For those who love a parade, love to sing, or who get a kick out of wearing antlers or a holiday costume, the Jingle Ride is a must for your holiday calendar.


  • When: Sunday, December 10, 2023,  10:30 AM – 1:30/2:00 PM EST
  • Check-in Registration begins at 10:00 am.
  • Ride Starting/Ending Location:  Kickstand Café (594 Massachusetts Ave, Arlington, MA 02476), the popular café in Arlington Center next to the Minuteman Bikeway. Delicious hot beverages and pastries are available for purchase from this bike-loving business.
  • Cost:  FREE
  • A $25 suggested donation is welcomed benefiting MassBike.  MassBike is dedicated to improving bicycling for all riders across Massachusetts.  Over the years, this colorful Ciclismo Classico tradition has raised thousands of dollars for other non-profit organizations like Horizons for Homeless Children.
  • Register Now!

The 18.5-mile ride (round-trip) follows the Minuteman Bikeway and then heads for Harvard Square, the Esplanade, Boston Common, and Newbury Street. The group makes occasional stops to sing carols for passersby, and enjoys bringing some unexpected holiday cheer to all who witness the group. The most-beloved stop is at Harvard Square, where the Harvard Square Business Association serves cookies and hot cocoa to the group – an especially welcome treat in chilly December! We also make an optional après-ride stop at the Menotomy Grill & Tavern just a mile from the ride’s end – come enjoy some free appetizers and more!

It’s a parade, not a race – so if you have a bicycle, we’d love your holiday spirit along for the ride!

IMPORTANT!  This is a ride on local bike paths AND major roads. We try to keep the route mainly on roads with bike lanes or other facilities, but all riders should be comfortable with and prepared for urban riding and all its unexpected excitement. We do follow all traffic laws and our fellow road users tend to be pretty jolly about our rolling parade of fun and merriment. And no matter how you decide to dress to celebrate the festive occasion, helmets are required for all Jingle Riders!

Would you like to join our ride leader crew or be a welcome volunteer for the ride? We need volunteers to make ride day roll smoothly! Sign Up Now.