What the hell is a Trail WhippAss and why do you want to become one? First off, none of us know what the hell a WhippAss is. Some say its a pun on words, some say its a mythical creature that runs through the forest seeking out mud, roots, rocks, and calls the gnarliest trails it can find home. Some say its BigFoots Sister, or the Yeti's father, or even Beowulf's long forgotten son. Theres a rumor that Trail WhippAsses like to meet up in groups and take selfies while jumping... nobody knows its just a rumor.