Arthur W. Levine was the Simsbury Community Band's first director. A Connecticut native from Meriden, Art received his musical training at Hartt College, University of Hartford. He came to Simsbury in 1969 to begin what was a continuing career, teaching instrumental music in the public schools. At the time of the Simsbury Community Band's beginning, Art was teaching at the junior high school and some of the elementary schools, before teaching instrumental music at Latimer Lane and Tootin' Hills elementary schools. Art started with the 13-member band in 1973 and retired as director in 1981.
William Channon served as the Simsbury Community Band's second director. Bill had come to Simsbury in 1956 to initiate the first formal music program in the Simsbury schools. For several years, he taught at all level, elementary through high school. The town and its schools grew and Bill focused on the high school starting in 1965. He then served as head of the school system's music department for 19 years until 1975. In addition, Bill started the summer Music and Arts Program in 1962. A brass player and arranger, Bill continued to teach privately. He was named Director Emeritus of the Community Band in 1995
Warren Gedstad was the Simsbury Community Band's third director, and was a musical product of the rich heritage of school and community music of the upper Midwest. His father was his first clarinet teacher and, while still in high school, he was clarinet soloist with the Sioux Falls, South Dakota Municipal Band. Warren received Bachelor's and Master's Degrees in music from the University of Illinois at Champaign-Urbana where he was a member of a variety of vocal and instrumental ensembles including the University's world renowned Symphonic Band. He was recognized by the University for outstanding contributions to University Bands. Before launching a business career, Warren was high school band director in Washington, Illinois. He joined the Simsbury Community Band in 1981 as both clarinetist and assistant director, and became Director in 1995.