Explore, Celebrate & Unwind!Enjoy live music at local breweries, lounges, outdoor restaurants, and community venues while discovering family-friendly activities, outdoor adventures, great dining, unique shopping, and hometown celebrations throughout Winsted and Winchester.
August is the perfect time to experience everything Winchester has to offer. Spend Thursday evenings at the Friends of Main Street Outdoor Summer Concert Series, step back in time at the American Mural Project's America 250 exhibit featuring the story of Connecticut's Great Flood of 1955, and celebrate cherished local traditions at the 76th Winchester Grange Fair & Flea Market and the 165th Winsted Fire Department Annual Carnival & Parade. Between events, explore the natural beauty of Highland Lake and the surrounding trails. Whether you enjoy boating, paddling, fishing, hiking, or simply relaxing outdoors, there's no shortage of ways to make the most of summer. Whether you're planning a day trip or a weekend getaway, August is the perfect time to explore Winchester. Upcoming Community Events
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 a cherished community tradition at the 75th Annual Winchester Grange Fair & Flea Market! Whether you're looking to browse unique treasures, enjoy homemade food and baked goods, admire local exhibits, or showcase your own flowers, produce, or baking, there's something for everyone. Join friends and neighbors for a day of fun, fellowship, and small-town charm. 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!
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