A Winsted-Winchester Christmas

November 29 and December 5-13 and 20, 2026

Enjoy this Year's Holiday Events!

It's the most enchanting time of the year! Get into the holiday spirit starting Sunday, November 29, in Winchester Center! At 4:30 pm, go to the green at Winchester Center for the Annual Graham Waldron Tree Lighting and Caroling.

On Saturday, December 5, join us in Downtown Winsted for exciting holiday shopping and fun with a Christmas Fair and Bazaar starting at 8:00 am!

We’re thrilled to announce that the beloved horse-drawn carriage rides are returning this holiday season! Join Friends of Main Street from 11:00 am to 1:00 pm at the corner of Main and Elm Streets for activities for the whole family.

Horse-Drawn Carriage Rides by Utopia Percherons of Goshen
Hot Cocoa served by Boy Scout Troop 1027
Holiday Storytelling at The Curious Cat Bookshop
🎶 Caroling by The Gilbert School Carolers strolling down Main Street
S'mores sponsored by Winsted Fire Department
Red Kettle Donations to The Salvation Army - Winsted Regional Service Center

Enjoy open houses and tours at the Beardsley Library, American Museum of Tort Law, the American Mural Project, and the Holiday Open Studios Weekend at Whiting Mills (December 5/6).

On Saturday, December 12 enjoy Breakfast with Santa at the YMCA, then head to Winchester Recreation Department activities at Rowley Playground Building at 2 pm, followed by walking to East End Park for S'mores, Caroling, and Tree Lighting at 3:30 pm. Enjoy the last Maker's Shoppes at Whiting Mills on Sunday, December 13 — rounding out Christmas in Winsted-Winchester!

🔔 2025 Event Schedule

November 29 – Winchester Center! (11 am to 7:30 pm)

Holiday Maker Shoppes (11 am to 4 pm) at Whiting Mills
Annual Graham Waldron Tree Lighting and Caroling (4:30 to 7:30 pm) on the Green at Winchester Center

December 5 – Downtown Winsted (8 am – 5 pm)

104th 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 House (10 am to 5 pm) American Museum of Tort Law, 654 Main St – Free admission and exclusive holiday deals!
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, live music, and refreshments
Horse-Drawn Carriage Rides (11 am to 1 pm) at the corner of Main and Elm Streets, Friends of Main Street / Northwest Community Bank
Hot Cocoa served by Boy Scout Troop 1027
S'mores sponsored by Winsted Fire Department
Holiday Storytelling at The Curious Cat Bookshop
🎶 Caroling by The Gilbert School Carolers strolling down Main Street
Red Kettle Donations to The Salvation Army

December 6 – 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!

December 12 – Downtown Winsted (9 am – 4:30 pm)

🎅🏼 Breakfast with Santa, Winsted YMCA, 480 Main Street (9am)
Winchester Recreation Holiday Event (2 to 3:30 pm) Rowley Recreation Building

– Pictures with Santa and The Grinch
– Decorate ornaments

🎄 East End Park Tree Lighting (3:30 to 4:30 pm)

– 🎶 Carolers
– Hot Cocoa
– S'mores sponsored by Winsted Fire Department
– Tree Lighting at 4:30 pm
December 13 – Downtown Winsted (11 am – 4 pm)

Holiday Maker Shoppes (11 am to 4 pm) at Whiting Mills

December 19– Winsted (5 – 7 pm)

"Gator" Christmas Parade, Winsted Fire Department. Emergency vehicles line up on Meadow Street, after which the parade follows a predefined route through town. 🚒 🚑 🚓

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