The Kenosha JROTC program was originally established at Reuther Central High School by General Order #22, 1 July 1995, and was redesigned by the Department of the Army as the Kenosha Military Academy, effective 17 January 1998. The unit was officially activated on 7 October 1998 with a formal ceremony held in the Reuther Central High School auditorium.

In September of 2002, the Kenosha Military Academy changed location from Reuther Central High School to Indian Trail Academy, today known as Indian Trail High School and Academy. The District added comprehensive education programming to the building, making it a general high school, along with keeping the specialized academies.

The Kenosha Military Academy cadets attend classes within the comprehensive high school, they participate in the athletic programs and they get the benefits of a performance-based, learner-centered leadership education and co-curricular programming of the JROTC curriculum.