In A Nutshell
The practice of dressing up as spooky characters originated among the early Christian peoples of Western Europe, from the seventh century on, since they were celebrating the arrival of the recently deceased into Heaven or Hell on the next day. This implied for the living that the souls of everyone who had died in the past year had been wandering on Earth, and now, with one last chance before their consignation to eternal fire, the souls of bad people were going to have their own little Mardi Gras for one night.
The Whole Bushel
The word “Halloween” is a contraction of “Hallow Even” (“evening”), which became “Hallowe’en” via the Scottish dialect. On this evening, Medieval Christians were reminded via the tolling of church bells to pray for their own souls in honor and remembrance of the brave people who had, for the sake of Jesus, died in horrible ways up to that time. If not tolling bells, town criers would dress all in black and call for the locals’ prayers and praise for the Saints.
Halloween is a Christianization of the Celtic feast of Samhain, pronounced “SOW-in.” In order to convert the Celts, the Christian missionaries of Saint Augustine’s time had to incorporate some of the Celts’ pagan practices into Christianity, most notably that of the Christmas tree. The three-day feast of Hallowmas coincides with the Celts’ primitive feast from sunset of October 31 to sunset of November 1, about halfway through the autumnal season. “Hallowmas” is the English contraction for “Mass of the Hallows,” and “Hallows” is another word for “saints.”
These saints are the martyrs of the Christian church, and people honored them by getting together and feasting in their names. That is, for November 1. The next day, the revelers continued the feast in honor of personal friends and family members who had died within the past year, while also praying for their souls to enter Heaven. It is a Lutheran custom to place candles on their graves on the night of the 31st, and an autumn graveyard filled with orange glowing flames is quite a portrait of Halloween.
Now with Christian influence, the three-day feast is properly called Triduum of All Hallows. “Triduum” is Latin for “three-day.” Another source of the spookiness of Halloween are the manners by which the martyrs died. Why do we watch horror movie marathons on the 31st? In part because the deaths of people like Saint Peter (crucified upside down) and Saint Lawrence (cooked to death) make for the prototypical Halloween horror show.
It did not take long for the concept to arise among the pagan converts and their descendants that if they were praying for the souls of their loved ones to get into Heaven, that meant that the souls of bad people had been kicking around Earth for a whole year, too. And if they had only one night left before going to Hell, they might go particularly wild. For the living of the Middle Ages, this meant the threat of indwelling by the spirit of someone like Ted Bundy.
Demonic possession was a real and terrifying fear in the Middle Ages, so to defend themselves against it, people masqueraded behind costumes to confuse the evil spirits looking for them. These costumes were not originally meant to be scary, but simply to cover identities.
Scary costumes were worn beginning in the 1500s throughout Western Europe and England originally to celebrate the deaths of the Seven Brethren. These were the seven children of Saint Felicitas, who, according to the Second Book of Maccabees, were brought before a tyrant and demanded to recant. When they did not, one by one they suffered their tongues cut out, their hands cut off, and were fried to death in shallow cauldrons. Then their mother was put to death, but none of the eight recanted. So children from the 1500s began celebrating the bravery of these martyrs by dressing up in horrid costumes of partly burned and scarred animal skins on All Hallows’ Eve. These costumes gradually changed to the various classic monsters.
Scary witch costumes and the like are the primary reason why some Christian denominations today denounce Halloween as the most sinful, non-Christian event of the year. The Puritans of 17th-century America, who hanged 18 people for witchcraft in the 1690s, not surprisingly preached hellfire and brimstone against it. They cited Exodus 22:18, “Thou shalt not suffer a witch to live.”