Join us on Main Street for Winsted’s 26th Fall Foliage Festival & Car Show! Celebrate the beauty of fall and discover why Winsted/Winchester is the perfect place to live, work, and play—offering the very best of town and country.

Main Street will come alive with a full day of fun, food, shopping, and entertainment! Browse the unique creations of crafters and artisans, shop with local vendors and businesses, and connect with our community organizations. There’s something for everyone, including kids’ activities, live entertainment, and plenty of family fun! 🎶🍁

And come hungry! 😋 Enjoy delicious offerings from food trucks, festival vendors, and local restaurants, with plenty of tasty choices to keep you fueled throughout the day.

🚗 REV UP YOUR ENGINES! 🚗

We’re excited to feature a spectacular Car Show as part of this year’s festival! Check out an impressive lineup of classic, muscle, and sports cars, with a variety of awards up for grabs. Whether you’re a serious car enthusiast or love a beautiful set of wheels, you won’t want to miss it!

🍂 Good old-fashioned family fun, right here on Main Street! 

Please remove all vehicles from Main Street—the retail side, including the areas in front of stores and restaurants—by 6:00 am on festival day. This will allow our team to safely set up the exhibitors, vendors, and Car Show, and prepare Main Street for the festival.