A highwayman is a thief who usually steals from travelers. The term is typically used in both fictional and non-fictional historical accounts. In fiction stories, he is usually a gentleman who has manners and uses non-violent threats to steal from travelers. In history, however, these thieves weren’t always gentlemen, well-mannered, or interested in avoiding violence. Still, many people who read historical fiction enjoy reading about dashing robbers who are romanticized as dark and dangerous, yet mannerly and courageous at the same time.
The legendary highwayman is usually described as a gentleman. This does not, however, mean that the robber was born into a higher class. Instead, historical fiction may paint him as coming from a higher- or lower-class family but depict him as having the manners, habits and dress of a gentleman. This thief typically covers his face with a kerchief and threatens his victims, usually with weapons, into handing over their valuables.
Interestingly, legendary highwaymen are often described as heroes. They are typically described as stealing from the wealthy while proving generous with poor people. Fictional thieves typically steal money and jewels as well as horses and livestock, and real ones stole these things as well. Additionally, fictional characters are usually depicted as expert horsemen who conduct their robberies while mounted on their horses or with their horses waiting nearby.
Unfortunately, the life of a highwayman was probably not as heroic or romantic as it might seem in historical fiction. Some did come from wealthy families and some were well mannered, but this description doesn’t describe the majority of highway robbers. Often, they did use brute force to steal from their victims, and some raped their female victims. In fact, one by the name of Tom Wilmot cut off a woman’s finger so he could steal a difficult-to-remove ring.
Perhaps surprisingly, some of these thieves were not men; there were women who stole from travelers as well. One, named Joan Bracey, was hung for her crimes in the 1600s. In fact, many highwaymen met their demise this way. In many cases, the robber's body would be left to hang for the public to see as a warning to those who might be considering the same occupation.
In the 1800s, patrolling police forces began to make life much harder for these thieves, and mounted robbers began to decline. By some historical accounts, the last highway robberies ended in the 1830s.