Join us on Main Street for the 24th Annual Fall Foliage Festival. Discover why Winsted/Winchester is the perfect place to live, work, and play, offering the best of both town and country while exploring the fall foliage throughout beautiful Litchfield Hills.

Arts and Crafts
Food and Drinks
Kids Activities
Live Music
Car and Motorcycle Show
Win Big

Our event has been a beacon of autumn splendor for the past two decades, attracting area residents and visitors from afar to downtown Winsted. They come to enjoy the crafters, artisans, vendors, local businesses, and organizations, with kids' activities and live music, plus tasty treats to tickle their taste buds, from food trucks to local restaurants. It's a day of good, old-fashioned, family fun you don't want to miss.

Car and Motorcycle Entry Fee $10 at the Gate.

​There are various awards up for grabs, too. These include the Peoples Choice Award, Motorcycle-Best Paint Job, Sports Cars-Best Engine, Best Paint, Best Wheels, and Muscle Cars-Best Engine, Best Paint, and Best Interior.