Hershey Highwayman Share definition Flag A man who likes bashing other male's turds. Kevin: Christ, look at the leather trousers on him, he must be a hershey highwayman. Hershey Highwayman by Dexter Von Shithaase April 25, 2010 0 0 Get merch Get the Hershey Highwayman mug. Buy Now — $32.95 See more merch