After building his own, "motorized bicycle" to pay tribute to his great grandfather, Cutler Gray rides 1000 miles just as "Buck DuSell" did over a century earlier during the advent of the now common "motorcycle". Along the way, Cutler and his support team learn just what it must have been like to take part in the original "endurance runs of 1908" - a competition in which "Buck" participated - competing against Walter Davidson of Harley Davidson among many other legendary "Test Pilots". Historical Documents and Newspaper Articles help to paint a portrait of roadside bike repairs, spontaneous camping, ironclad camaraderie, and the simple joys of riding. It is through the invention of the motorcycle, that the group makes connections not only to Buck DuSell's past, but also to their own.