Center stage in the Town of Windham 's cultural life is the Windham Chamber Music Festival, a not-for-profit organization that presents a series of year-round classical music and classical jazz concerts in the historic Windham Civic Centre (the old Centre Church ) on Main Street in the Village of Windham . Nationally acclaimed visiting artists are presented, and performances have been featured on National Public Radio's "Performance Today."

Special events like The Autumn A-Fair always feature bands and solo performers in a wide range of musical styles from jazz to folk, rock, Dixieland, and country & western.