The ride begins near Moultry Creek at present-day Treaty Park, where the Treaty of Moultrie Creek was signed in 1823 between Seminole leaders and the federal government. From there, the route moves briefly through the urban edge of St. Augustine before reaching quiet farming communities such as Bakersville, Sanksville, and Picolata, following the Saint Johns River beneath oak canopies and past historic riverfront homes.
After passing through Tocoi, Riverdale, and Racy Point, the ride enters conservation areas such as Twelve Mile Swamp and Deep Creek. The final miles follow the East Coast Greenway on a former railroad corridor, crossing Spuds, Armstrong, Elkton, and Vermont Heights, before returning to the starting point.