Top 3 Halloween Legends & Origins

Bloody Mary, the Headless Horseman, that one haunting story passed down throughyour family- we all know of a chilling tale or two told around the fire during this time of year, involving ghosts or spirits or other ghastly subjects.

In honor of the Halloween season, we’ve compiled a list of some of our favorite legends and their frightening origins.

Will o’ Wisp & Jack o’ Lantern

While we commonly wouldn’t think of two common ideas- a mysterious fairy light leading travelers astray, and a common pumpkin carved and lit beside doorsteps- as the same, their origins are deeply intertwined, to the point that one refers to the other in some lands. Classically, these two legends explained by two sinners- named Will and Jack, as you might expect.

Will the Smith, (not to be mistaken for the famous actor,) was such a captious scoundrel during his life that when he passed, he was denied from the gates of the afterlife, and told to return after his second life. And yet, his second life was twice as much intolerable, and so he was cursed to roam the Earth for eternity.

The Devil himself, impressed by Will’s evils, offered him an eternally burning coal to keep him warm during the cold nights. Will took this coal and decided to make himself a torch, and lure innocents into danger. Thus, we have Will o’ the Wisp.

Stingy Jack’s story holds many variations, but it always holds certain themes. Jack is typically a drunkard known to be a dreg of society and a manipulator, a silver-tongued snake. When the devil comes to collect his soul, he makes a final request- that he should drink ale before he departs to the underworld. Seeing no reason not to agree to this, the devil allows him a visit to a pub.

Once Jack has had his fill, he asks the tab be paid- and convinces the devil to transform into a silver coin to do so. Satan is impressed by Jack’s unending tactics and trickery, and so agrees, leaping into Jack’s wallet when no mortal is looking. But inside Jack’s wallet is a crucifix, and so the devil cannot escape his form. Jack bargains for ten more years, and in exchange, gives the devil his freedom.

Ten years from that date, Satan arrives to claim Jack’s soul once more, and Jack seems to accept this. He gives the devil one more final request, a simple apple to fill his starving stomach before they go. Satan, still holding respect for Jack’s evil, again acquiesces. As he climbs the apple tree to retrieve one, Jack quickly surrounds the trunk of the tree with crucifixes, rendering the now very frustrated devil incapable of climbing down. Jack demands that his soul is never taken to the underworld, and in exchange frees Satan once more.

Much like Will, when Jack does eventually die, he is denied from the gates of heaven. Forced to go, he seeks out Satan and begs to be allowed into the underworld, but Satan, keeping his terms, cannot and will not accept Jack’s soul. He flicks an ember to Jack, whether out of pity or spite is debatable, and Jack from then on is doomed to roam the land without anywhere to reside. He sets the ember inside a hollowed-out turnip, his favorite food, and uses it as a lantern as he wanders. And so, we have Jack o’ the Lantern.

Bloody Mary

The classic sleepover game we’ve all heard about, grabbing a couple of your more fearless friends and chanting a few times (three or thirteen or seven or however, depending on who you ask) in a darkened, likely candle-lit mirror will display before you the agonized spirit of Bloody Mary herself. What she’ll do when she gets there is up to the particular tale- will she tell your future? Kill your friends? Tear your face off? Speak with you? It all seems to depend on what version of the legend you’ve heard.

The practice likely first originated from the mirror divinations covered in a previous article, where girls would attempt to see their future husband in the mirror on Halloween night in a variety of ways, usually involving a darkened mirror and a candle’s light.

However, the origin of the legend of Bloody Mary herself is well-debated: some say she’s the spirit of a particularly vengeful witch executed in the Salem witch trials, some associate her with Mary I of England, who executed many for heresy and gained the same nickname, and some further still believe that her origin had something to do with Elizabeth Bathory, who was supposedly convicted for the murder of an uncountable young girls for the purposes of bathing in their blood in the belief it would keep her young.

Sleepy Hollow

One tale of the Headless Horseman, Sleepy Hollow, has much more clear-set origins than most other stories do. Published in 1820, the story The Legend of Sleepy Hollow is by far the clearest source of the Horseman’s popularity, though not the very first time he was heard of- the motif of a soldier on horseback who’s lacking his head has been shared since at least the Middle Ages.

The Sleepy Hollow story follows one Ichabod Crane, a lanky, heavily superstitious teacher in a town known for its ghosts and supernatural influence. Ichabod seeks the hand of a rich young woman, and finds competition in the town’s local rowdy hero Brom Bones. For some time, each man vies for the young Katrina’s hand in marriage, and Ichabod eventually asks for her hand at an Autumn harvest party, but she does not give it.

On the crestfallen ride home through the woods, Crane finds his mind accosted by the dark legends that he had heard during the party, and finds himself nervous as he navigates. As he passes under a purportedly haunted tree, he encounters another rider in the distance, cloaked and silent. Put off by the apparent companion’s silence, he is horrified to discover that the fellow traveler’s head is not on his shoulders, but on his saddle.

In a desperate frenzy, he begs his temperamental horse to rush to the nearby bridge, hoping that its rumored supernatural powers would dispel the spirit. He nearly makes his way to freedom before the Headless Horseman clambers over the bridge, rears his horse, and hurls his head at Ichabod’s face.

Ichabod is never seen again after that night, and Katrina ends marrying Bones, who seems oddly knowing whenever Ichabod’s story is brought up.

What is your favorite Halloween legend?  Let Your Geek Sideshow and tell us in the comments below!

This October, we’re putting the “eek” in Geek from October 24th-31st for our annual Spooktacular celebration!  Head to for all the creepiest content, most ghoulish giveaways, and most devilish deals to get you in the mood for Halloween.