This December, whether you’re visiting for a day or celebrating a full holiday weekend, wander down one of Connecticut’s longest—and most magical—Main Streets! Discover unique shops, vintage treasures, delicious food, live music, craft brews, and even axe throwing. Soak in the twinkling lights, the small-town charm, and the joyful community spirit—and make holiday memories that will warm your heart all season long!
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Upcoming Community Events

Date
Event | Start Time
Dec 1-18
Winsted Winter Wonderland Window-Decorating Contest, Friends of. Main Street
Dec 6
A Winsted-Winchester Christmas | Downtown Winsted (8 am – 5 pm)
Dec 7
A Winsted-Winchester Christmas  
​Downtown ​Winsted (10 am – 5 pm)
Dec 10
​​Blue Christmas, Winchester Center Congregational Church, 1 West Street, Winchester Center (7pm)
Dec 12
14th Annual Freezin’ for a Reason Sleep Out and Fundraiser, Northwestern CT YMCA, East End Park (6pm)
Dec 13
🎅🏼 ​Breakfast with Santa, Winsted YMCA, 480 Main Street  (9am)

Winchester Recreation Holiday Event (2 pm)​​​​ Rowley Recreation Building
            –  Pictures with Santa and The
                 Grinch
            –  Decorating Ornaments
            –  Pictures with 
🎄 East End Park & Tree Lighting  (3:30 pm)
​             –  Hot Cocoa
             –  Carolers
             –  S'mores sponsored by Winsted Fire
                   Department
Dec 14
Holiday Makers Shoppes, Whiting Mills, 100 Whiting Street (11am)
Dec 20
Gator Parade Tailgate and Watch Party! Faith Bible Church, 368 Main St (5pm)

The Gator Parade, Winsted Fire Department, Main Street (5pm to 7pm)
Dec 26
Happy Hour Piano Series: Dan Ringuette, American Mural Project, 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!​
Celebrate the holidays in Winsted-Winchester – so many events to enjoy! When you shop and eat local, you’re not just buying products—you’re investing in people, dreams, and the heart of your hometown. ❤️ #SupportLocal​  – Background picture courtesy of  Utopia Percherons.

​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!