The Ride happens the 3rd Saturday of every September and is the official Ride route to commemorate the Trail of Tears. The route follows the Tennessee River as it winds across northern Alabama from Bridgeport to Waterloo. Native Americans, Cherokees and the other tribes, were forced to walk from Ross's landing near Chattanooga to waterloo. At waterloo they joined with others to continue their march by foot to the designated Indian territories in Oklahoma. This route is designated as the official route that is recognized by the Alabama Indian Affairs Commission as "dedicated to following the historical route to Waterloo, AL."

The Laconia Motorcycle Week rally is often mentioned in the same breath as events in Daytona, Florida and Sturgis, South Dakota. After all, these are three of the most popular motorcycle rallies in the country, drawing in over a million riders and motorcycle enthusiasts, combined, every year.

But Laconia can make a claim that the other two cannot. Often referred to as the Oldest National Motorcycle Rally, these roots reach back to the summer of 1916, when a Gypsy Tour gathered for several days at Weirs Beach on the southern shores of Lake Winnipesaukee.