In the fall of 1993 in Garden City, Michigan, Chuck (Tramp) Dare and the commander of Michigan's American Legion Post 396, (Polka) Bill Kaledas shared an idea to start an association of motorcycle enthusiasts within The American Legion. The two Legionnaires--both long-time riders--wanted to provide an environment where post, Auxiliary and Sons of The American Legion members who shared a common love for motorcycles could come together.

Dare and Kaledas prepared a letter to Michigan Department Adjutant Hubert Hess. In his November 19th, 1993 reply, Hess agreed with the concept and stated that it "sounds like a great idea...let's work it out." In further correspondence and follow-up phone conversations, Hess gave the two riders instructions on how to manage such a program at the post level. He also provided information on how to get approval for the use of the American Legion Emblem and to get this program recognized and supported by the membership. The members of Post 396, at a regular Legion meeting, considered a resolution for a new post program to be known as the "American Legion Riders". The resolution passed, establishing the birth of the new program.

Dare and Kaledas, joined by 19 other founding members of the Garden City Post 396, soon found themselves inundated with requests for information about the new organization, and agreed to establish a central source of information about the Riders, to make certain that the new "chapters" around the country formed not as motorcycle clubs or gangs, but as Legionnaires, Auxiliary, and SAL members joining to ride as members of The American Legion family. Pat Babcock, an SAL member from Michigan, soon established a website with sample by-laws and instructions for forming new Chapters.