It's going to be a Winter Wonderland!

🚂 As the seasons change, Main Street transforms from eerie storefronts into a Winter Wonderland right before your eyes. It’s a place where we come together each year to create unforgettable memories, and where children can dream of catching a magical ride on the Winsted Winter Express to the North Pole. 

Shop along Main Street this holiday season for unique 🎁s for your family and friends. Enjoy the festive decorations in the windows. Join us for holiday fairs, a church bazaar, 20th Anniversary of the Holiday Open Studio Weekend at Whiting Mills, caroling, the unveiling of an ice sculpture, pictures with 🎅, and the annual🎄lighting at East End Park. Don’t miss the Sandra Boynton Christmas event at the American Mural Project on Whiting Street! – Wishing You a Season Filled with Light and Love 🦌

Don't miss out on any of the fun - sign up for THE WEEKLY to stay up-to-date on all community events throughout the year!

Upcoming Community Events

Date
Event | Start Time
Dec 1
A Winsted-Winchester Christmas 
Winchester Center (4:30 – 7:30 pm)​​
  • Annual Christmas Tree Lighting & Carol. Singing (4:30 to 7:30 pm) at Winchester Center Congregational Church
Dec 7
A Winsted-Winchester Christmas ​Downtown Winsted (8 am – 7 pm)             –  Music
            –  Pictures with Santa
            –  Crafts
            –  Hot Cocoa
             – Ugly Sweater Contest
             – Carolers
             – Pictures with The Grinch ​              – Holiday Decorations sponsored by Women Business Owners of Winsted (W.O.W)
             – S'mores sponsored by Winsted Fire Department
Dec 8
A Winsted-Winchester Christmas  
​Downtown ​Winsted (10 am – 5 pm)
Dec 11
​Blue Christmas Service, Winchester Center Congregational Church, 1 West St., Winchester Center (7pm)
Dec 13
13th Annual Freezin' for a Reason
​ Northwestern Connecticut YMCA, East End Park
Dec 14
Breakfast with Santa, Winsted Y, 480 Main Street  (9am)
Dec 15
Makers Shoppes, Whiting Mills, 100 Whiting Street (11am)
Dec 18
Holiday Tree Decorating Contest-Awards, Winsted Recreation Department, 338 Main Street (10am)
Dec 21
The Gator Parade, Winsted Fire Department, Main Street (5pm)​
Dec 27
Piano Happy Hour - Dan Ringuette, Winter Holidays Sing-a-Long, AMP, 90 Whiting St (5pm)
Dec 31
🥳​ Happy New Year's Eve!

Check out Winsted's Growing Music & Comedy Scene
Music in a Mile!


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Welcome. 

We're making positive things happen in Winsted since 1999!

Friends of Main Street Winsted is a 501(c)(3) not-for-profit organization dedicated to supporting the historic preservation, beautification, and economic growth of Winsted.

We achieve this by helping to attract new businesses, support existing businesses, and encourage traffic to downtown.

Donations are always welcome!​
Children can imagine themselves aboard the magical Winsted Winter Express, embarking on an unforgettable journey to the North Pole. The Community Health & Wellness Center has allowed Friends of Main Street to transform the empty windows at its building at 372 Main Street into a festive holiday mural designed and painted by artist Michael Genovese. This mural pays tribute to the trains that once traveled to Winsted.

​Proud member of:
Strong supporter of:
Strong supporter of: 
​Northwest CT Main Street PROMISE Program
​It’s purpose is to help strengthen the region’s town centers and main streets through an iterative four-year collaboration.

Whatever your interests may be – Winsted Has It!

Get your 2024 Tourism Map on Main Street!

Are you ready to explore Winsted and its surrounding towns this summer? Make sure to grab a copy of the new 2024 Tourist Maps, available in over 40 locations downtown. 
These comprehensive maps are easy to use, highlighting various cultural attractions, outdoor activities, excellent restaurants & cafés, and unique shops. There are so many new shops and restaurants, along with the addition of the new Hartford HealthCare HealthCenter ER and heliport, The Joyner Center, CT State Northwestern, American Mural Project, American Museum of Tort Law, the Sue Grossman Greenway and Tatros Park – your adventure is bound to be exciting!