What is a Highwayman?

N. Madison
N. Madison

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.

Robin Hood is a legendary highwayman, as he stole from the wealthy and proved to be generous with the poor.
Robin Hood is a legendary highwayman, as he stole from the wealthy and proved to be generous with the poor.

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.

A highwayman usually covered his face with a kerchief before he brandished any weapon that was meant to threaten his victims into surrendering their valuables.
A highwayman usually covered his face with a kerchief before he brandished any weapon that was meant to threaten his victims into surrendering 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.

N. Madison
N. Madison

Nicole’s thirst for knowledge inspired her to become a wiseGEEK writer, and she focuses primarily on topics such as homeschooling, parenting, health, science, and business. When not writing or spending time with her four children, Nicole enjoys reading, camping, and going to the beach.

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Discussion Comments


@Azuza - Even though you may have outgrown your highwayman fantasy there are some adaptations of the poem you might still enjoy.

Lorena McKennitt made a song out of the poem that I really enjoy. You can find it on her album "Book of Secrets." There was also a movie adaptation in 1951 as well as a novel written in 2002 that are both called "The Highwayman." I think these versions may spark your imagination again!


@manykitties2 - I think my favorite example of a highwayman in literature is of course the famous poem "The Highwayman" by Alfred Noyes. It's a very romantic poem about a highwayman who falls in love and of course the story ends tragically.

I read that poem at some point when I was in middle school and I remember dreaming of being swept of my feet by a dashing man on horseback. Of course, middle school me completely glossed over the fact that a highwayman is a criminal. It was a fun fantasy though!


Can anyone think of any favorite stories or movies you have enjoyed that featured a highwayman?

I have watched numerous films over the past decade that have a highwayman as their central character. I have found them to be a very intriguing lead character in dramas and romantic films because of the balance between being good and evil they struggle with.

The gentleman robber of old, turned to a life of crime for some noble reason seems a little cheesy to me sometimes, but I still enjoy the idea. I think it is a good idea to check out some of the various films that feature a highwayman if you are curious as to how this character can be portrayed in romance and drama.


The highwayman is a very popular character in horror stories, although they are rarely depicted as gentleman. The term seems to have been adopted to describe those that stalk the highways looking for victims who are traveling and won't be missed easily.

Not only do highwayman steal from their victims in horror stories, but they often deal out some sort of torture, whether it is psychological or real. I have found that a lot of crime dramas will create a character with the highwayman base, and take creative license from there. Often they turn the highwayman character into a serial killer that finds easy pray alongside quiet roads.

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