In the fall of 1993 Chuck (Tramp) Dare shared a dream with then Post Commander (Polka) Bill Kaledas at the American Legion Post 396 in Garden City, Michigan. The idea came about to start a motorcycle association that would operate within the American Legion. The idea was to provide an atmosphere whereas Post, Auxiliary and S.A.L. members, who shared an enthusiasm for motorcycles, could come together. It was meant to be a family oriented group.

The idea was brought up at a Post 396 meeting to sponsor the group to be known as the "American Legion Riders". It was passed by their members and thus became first American Legion Riders group.

By 2007, the American Legion Riders program had grown to over 600 chapters in the United States and overseas.