A highwayman was a robber on horseback who stopped travelers on roads and highways, demanding their money and valuables at gunpoint. These bandits were most common in England from the 1600s through the early 1800s, before modern police forces existed.

Picture a masked rider galloping out from the trees on a lonely road at night, blocking a stagecoach and shouting the famous command: “Stand and deliver!” That meant hand over your valuables or face trouble. Highwaymen typically robbed wealthy travelers, mail coaches carrying money, or anyone journeying between towns on isolated roads.