November 30 and December 6/7, 2025 Enjoy this Year's Holiday Events!
It's the most enchanting time of the year! Children can imagine themselves aboard the magical Winsted Winter Express, embarking on an unforgettable journey to the North Pole – plus plenty of shopping! Get into the holiday spirit starting Sunday, November 30, in Winchester Center! At 4:30 pm, go to the Winchester Center Congregational Church for the annual tree lighting and caroling.
On Sunday, December 6, join us in Downtown Winstedto explore Main, Rowley, Lake, and Whiting Streets for exciting holiday shopping and fun!
You won't want to miss taking pictures at the North Pole in front of our 75 ft mural – The Winsted Winter Express – located at 372 Main Street, honoring the trains that journeyed to Winsted. At 1:00 pm, Friends of Main Street and Northwest Community Bank will have a ribbon cutting for a special Ice Carving.
Head to Winchester Recreation Department activities at Rowley Playground Building at 2 pm and then to East End Park for S'mores, Caroling, and Tree Lighting at 4:30 pm. Cap off the day at A Sandra Boynton Christmas at the AMP at 7:00 pm. Enjoy visiting the American Museum of Tort Law, the American Mural Project, and the Holiday Open StudiosWeekend at Whiting Mills –rounding out Christmas in Winsted-Winchester!
