Here are two Halloween fairy tales. The first is for adults, the second for children.
Long ago and far away, everybody imagined the heavens and the earth as stuffed with spiritual beings. There was no such thing as “space” (the room you’re in is literally saturated with these spirits). Most of these beings had good intentions. But many did not. They were evil, diabolical. They sought to deceive us. And they were serious about this.
So serious that most folks felt the best we can do is “get by” in life, get past these demons. They felt that way because these spirits were “almost indistinguishable” from the physical objects they inhabit. The boundary between the spirit and bodily flesh was imagined as porous. Spirits good and bad permeate our bodies, making holy aims (like “be perfect as my Father in heaven is perfect”) unlikely to be achieved. Most societies assumed most folks “were not going to live up to the demands of perfection.”
But not living up didn’t mean giving up. Societies instead created festivals mocking good standards. These gave people a place to blow off a little steam so that the whole system wouldn’t fly apart. Carnival is an example, a festival of misrule and mayhem where the normal order would be temporarily suspended, reversed. (ex: fools would be made king for a day).
Crazy? Like a fox. Medieval societies recognized that while chaos is dangerous and must be contained, order constantly threatens to become rigid, repressive, and deadening. Healthy order requires periodic plunges into chaos, seeing through these festivals to those forces always present beneath the surface in the enchanted universe. If we don’t see through, life becomes unbearable, brittle, lifeless (today we call this left-brained).
This is why Carnival in the medieval Christian calendar was immediately followed by 40 days of Lent (the word carnival coming from the Latin carne vale: “farewell to flesh”). “Letting yourself go” for a bit was meaning-full, imagined as the first step toward self-renunciation. So was Halloween (All Hallows Eve), which was immediately followed by the Feast of All Saints, or “All Hallows,” the feast celebrating the dedication day of All Saints Chapel in St. Peter’s at Rome in 840AD. Halloween thereafter spread, all the way to Ireland, where the Irish embraced it with great enthusiasm, loving all the sorcery, magic, mayhem and mysticism.
But that was long ago and far away. Beginning some 500 years ago, on continents named Europe and North America, societies discarded the image of an enchanted heavens and earth stuffed with supernatural beings—God, angels, ghosts, ghouls, goblins. These “western” societies became “denuded of the mystical.” They became dis-enchanted.”
As a result, few Christians saw through festivals like Halloween to the faith. This portended “the final triumph of the Hollow Men,” wrote Evelyn Waugh, the British Catholic novelist (most famously of Brideshead Revisited) who “lost the ability to feel or think deeply about anything.” Christians meant well but “hollowed-out” the meaning of Halloween.
Today, most only see to the candy and cute costumes. Ghosts and goblins and magic? They warn the kids: Not Real. Jesus is Real. Other Christians avoid Halloween altogether, mistakenly believing they’re buffering their kids from the “secular” world by having “Harvest Parties.” Both are unhelpful. They cause kids to imagine the faith as dis-enchanted, lifeless.
Thank God for the Irish. In the 1840s, Irish immigrants fleeing their country’s potato famine brought Halloween to America. At that time, the favorite pranks in New England included tipping over outhouses and unhinging fence gates. A century later, an Irishman, C. S. Lewis, wrote that ghosts and goblins shouldn’t necessarily spook us. They instead evoke a “welcome hint of wildness and uncertainty into a universe that is in danger of being a little too self-explanatory.” A little too dull. Dis-enchanted. Lifeless.
Enough of the adult stuff. Here’s the good news. The Irish brought with them a Halloween fairy tale for children. I can’t vouch for its authenticity, but here it is.
“Once upon a time, there was a man named Jack, a notorious drunkard and trickster. One day he tricked Satan into climbing a tree. Jack then carved an image of a cross in the tree’s trunk, trapping the devil up the tree. He then made a deal with the devil: if the devil would never tempt him again, Jack would promise to let him down the tree. The deal was struck.
Leaving Jack stuck. After he died, Jack was denied entrance to heaven because of his deal, but he was also denied access to hell because he had tricked the devil. Instead, the devil gave him a single ember to light his way through the frigid darkness. The ember was placed inside a hollowed-out turnip to keep it glowing longer.
Now in Ireland, the Irish used turnips as their “Jack’s lanterns.” But Irish immigrants found pumpkins were far more plentiful in America than turnips. So the Jack-O-Lantern in America was a hollowed-out pumpkin, lit with an ember. Tonight, [parents: insert your children’s names] we’re going to carve our pumpkin and have it lit with a candle [or LED light… whatever]. Some our pumpkins have very scary faces. But don’t be afraid.
The light inside our pumpkin reminds us that God’s word is a lamp to light our way. But we’re supposed to not just see to God’s Word, to the light in the pumpkin, but also by its light see through it, out to the world and how we ought to live. Is that cool or what?
… now kids, who’s ready to carve our pumpkin?”
 Charles Taylor, A Secular Age (The Belknap Press of Harvard University Press, 2007), 61.
 From Max Weber: Essays in Sociology, (Oxford University Press, 1946), 155.
 C. S. Lewis, The Discarded Image: An Introduction to Medieval and Renaissance Literature (Cambridge University Press, 1964), 122.