The Orillia Wind Ensemble was formed in Nov. 1986 as the Orillia Concert Band. At the time, newly retired Toronto music teacher Bob Plunkett was invited to conduct the band. Under his leadership, the band began presenting programs in 1987 that have become an important part of the musical life of Orillia and surrounding areas establishing a reputation for high musical standards.

Upon Plunkett's retirement in 1997, Roy Menagh became the conductor and continued to develop the level of musicianship and establish the series concept of concerts that the ensemble now presents. 

The name of the group was changed to the Orillia Wind Ensemble when Menagh took over to reflect the new direction of the band program. However, it is still a community band made up entirely of local volunteer musicians who seek an outlet for musical performance and have a wish to contribute their musical talent for the enjoyment of their audiences.