Discover Autumn in Winchester!

October is a beautiful time to visit Winsted/Winchester, when crisp autumn air, colorful foliage, and a full calendar of seasonal events create the perfect backdrop for a fall getaway. Spend the day exploring local shops, enjoying great food and craft beverages, discovering art and history, or getting outdoors to take in the beauty of the Litchfield Hills. Then stay awhile and enjoy the welcoming small-town spirit that makes our community special.

There’s something happening throughout the month. From fall festivals, community cleanup, and live music to family-friendly Halloween fun, community celebrations, shopping, and special programs, October offers plenty of reasons to explore Winsted and Winchester.

Upcoming Community Events

Date
Event | Start Time
Oct 3
4th Fall Cleanup, Conservation Commission/ Friends of Main Street, East End Park (9:30 am)

LIVE @AMP: Latanya Farrell, American Mural Project, 90 Whiting St (8 pm)
Oct 3-4
4th Annual Halloween Spooktacular at Whiting Mills, 100 Whiting St (10 am)
Oct 4
Fall Fest, Little Red Barn Brewers, 32 Lake St (12 pm)
Oct 9-11
Riverton Fair, on the Fairgrounds (26 Main Street) in historic Riverton, CT (see fair schedule)
Oct 10
Tag Sale, Winchester Grange, 100 Newfield Rd (9 am)

Walking for Carrie, Little Red Barn Brewers. 32 Lake St (11 am)
Oct 11
Your Voice Matters, American Mural Project, 90 Whiting St (12pm)
Oct 16
AMERICA 250: Film and Talk, American Mural Project, 90 Whiting Street (10 am)​
Oct 23
Sip & Shop After Dark, Whiting Mills, 100 Whiting St (5 pm)

Piano Happy Hour: Ysanne, American Mural Project, 90 Whiting St (5 pm)
​
Haunted Hallways, Northwest CT YMCA Winsted Branch, 480 Main St (5 pm)
​
Halloween Party, Winsted Lions Club, Crystal Peak, 164 Torrington Rd (6:30 pm)
Oct 24
Halloween Window Painting Contest,​ Friends of Main Street, 398 Main St (9 am)
​
​Trunk or Treat, Winsted Recreation, Rowley Street Playground (5:30 pm) ​
Oct 29
The Phantom Of The Opera with Live Music!  American Mural Project, 90 Whiting St (7 pm)
Oct 31
Trick or Treat on Main Street, Winsted Recreation,  Main St (11 am)

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!​
We love decorating all the poles along Main Street for the Fall Foliage Festival & Car Show, and this year’s cornstalks came from right here in our community!

We sourced them locally from a new Main Street shop, Laurel City Garden & Gifts

Be sure to stop by 896 Main Street for all your fall decorating needs, in-season veggies, and unique gifts. Supporting our local businesses helps keep Main Street vibrant! 

​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!