FRIENDS OF MAIN STREET
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A Winsted-Winchester Christmas 

Picture
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 Winsted to 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 Studios Weekend at Whiting Mills –​ rounding out Christmas in Winsted-Winchester!


2024 Event Schedule

December 1
 – Winchester Center! (4:30 pm) 
  • Annual Tree Lighting and Caroling (4:30 to 7:30 pm) at Winchester Center Congregational Church 

December 7 – Downtown Winsted (8 am – 7 pm)
  • 102nd Christmas Fair (8 am to 3 pm) at First Church of Winsted
  • Christmas Bazaar (9 am to 2 pm) at St. Joseph Church ​
  • Holiday Open Studios Weekend (10 am to 4 pm) at Whiting Mills
  • Mural Tours (10 am to 5 pm) at American Mural Project, 90 Whiting St –Free coffee, tea, cocoa, and hot cider!
  • Holiday Open House (11 am to 1 pm) at Beardsley Library, 40 Munro Pl – Special visit with Santa, crafts, music "The Substitutes," and refreshments 
  • Holiday Open House (11 am to 4 pm) American Museum of Tort Law, 654 Main St – Free admission and exclusive holiday deals!​​
  • 🚂 Ribbon Cutting–Winsted Winter Express Ice Sculpture (1 pm) at 372 Main Street, Friends of Main Street / Northwest Community Bank ​
  • 🎅🏼 Winchester Recreation Holiday Event (2 to 4:30 pm)​​​​ Rowley Recreation Building
            –  Music
            –  Pictures with Santa
            –  Crafts
            –  Hot Cocoa
             – Ugly Sweater Contest
             – Carolers
             – Pictures with The Grinch
  • 🎄Tree Lighting at East End Park  (4:30 pm)
​              – Holiday Decorations sponsored by Women Business Owners of Winsted (W.O.W)
             – S'mores sponsored by Winsted Fire Department
  •  🐮 A Sandra Boynton Christmas  (7 pm) at American Mural Project​

​December 8 – Downtown Winsted (10 am – 5 pm)
  • Holiday Open Studios Weekend (10 am to 4 pm) at Whiting Mills
  • Mural Tours (12 to 5 pm) at American Mural Project, 90 Whiting St – Free coffee, tea, cocoa, and hot cider!

2024 Holiday Events!

​Wishing you a Season Filled with Light, Love, and Wonder. ​

© 2025 Friends of Main Street Winsted-Winchester, Inc., PO Box 18, 398 Main Street, Winsted, CT 06098
  • HOME
  • ABOUT
    • Mission, Location & Hours
    • What We Do
    • Work, Play, Day Tripping: Winchester
    • Board of Directors
  • SUPPORT
    • Donate & Volunteer
    • Sponsors
  • EVENTS
    • Bubble & Truffles 2025
    • Restaurant Week
    • Earth Day Cleanup
    • Flowers on Main Street
    • Summer Concert Series
    • Fall Foliage Festival >
      • 25th Fall Foliage Festival
      • Sponsor Opportunities
      • Vendor Application
    • Fall River Cleanup
    • Halloween Window Painting
    • A Winsted-Winchester Christmas
  • CALENDAR
    • Community Calendar & THE WEEKLY Newsletter
    • Blog
  • FOOD, BREW, FUN & NECESSITIES
    • Antiques
    • Attractions
    • Food, Brew & Catering
    • Necessities
    • Recreation & Exercise
    • Salons & Personal Services
    • Shopping
  • CONTACT