Holiday Stroll in Ridgefield

Fri Dec 5, 2025 - Sat Dec 6, 2025
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Repeating every week — Fridays, and Saturdays through December 6, 2025.
6:00pm ET
Age: All Ages
Price: Free
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Ridgefield, are you ready to stroll into the holiday season? T Save the dates for a weekend of merry-making, music, and more.

Here’s the rundown:

Friday, December 5th

  • DJ spinning holiday hits: 6-9 PM
  • Toy Soldiers marching down Main Street & Bailey Avenue: 6-9 PM
  • Victorian Carolers jingling all the way: 6-9 PM
  • Horse & Carriage Rides (pickup at Veterans Park Elementary & Ridgefield Library): 6-9 PM
  • Special Performances: Hearts in Harmony: Caroling for a Cause will be singing merry melodies at Veterans Park Elementary: 6-9 PM;
  • A.C.T. of CT Youth Choir will be performing on the steps of the Ridgefield Library’s historic Morris Building: 6-9 PM
  • Keeler Tavern Museum & History Center: Open House: 5-7 PM
  • North Pole Alert: Experience the magic of the holiday, as the Lounsbury House transforms into Santa’s HQ with Santa & Mrs. Claus, live reindeer, and postcards for our troops: 6-9 PM

Saturday, December 6th

  • DJ keeps the holiday beats going: 12 PM-4 PM
  • Outdoor Holiday Market on Bailey Avenue: 12-4
  • Toy Soldiers return for more Main Street magic: 12 noon -3 PM
  • Santa will be strolling down Main Street, spreading cheer and greeting his fans along the way! 2:30-4:00 PM
  • Holiday Pony Rides at Veterans Park Elementary: 12-2
  • Bernese Mountain Dog Parade: Meet and mingle at 12 PM at St. Stephen’s courtyard, with a parade to Jesse Lee Memorial Church at 1 PM. (please note: parking will not be available at St. Stephens)
  • Special Performances by the A.C.T of CT Youth Choir will perform on the steps of the Ridgefield Library’s historic Morris Building: 2 PM
** Activity dates/times are subject to change. Please click through to the activity website to verify.