Halloween can be a magical time for any kid: candy, costumes, and the chance to scare and be scared. It’s a time when convention is upended and the symbolic power to punish and reward – to trick or to treat – is granted to the least powerful among us, to children. The only thing required is the wearing of masks, but sometimes, putting on a mask is all a part of growing up.
When Dylan was six years old, he carved his first Halloween jack-o’-lantern. Dylan’s dad had spent the afternoon with him at his mother’s house. “My parents had been split up for about a year,” Dylan tells me. “So, I think that was the first Halloween after.”
By the time his father left that evening, Dylan had a large handsome pumpkin with a gaping, toothed mouth, arched triangle eyes, and a matching nose.
“I guess it was a real old school pumpkin,” Dylan recalls. “I think that was all my dad knew how to make.”
After dinner with his mother, Dylan wanted to take his jack-o’-lantern to the front porch, but his mother had other ideas. “My mom wasn’t really into the whole giving-out-candy thing,” Dylan tells me. “We just turned off the lights so no one came to the door.”
After the last of the trick-or-treaters went home, Dylan took his jack-o’-lantern to the porch.
As a consolation for sitting in the dark for two hours, Dylan’s mother had even let him light the candle himself.
Dylan carefully placed his jack-o’-lantern on the porch table facing the street with an orange grin. Dylan took a few steps down to the sidewalk to see what it looked like from the street.
In the dark the pumpkin looked suitably terrifying to Dylan. “Then I looked down the street and I saw this orange mess on the road,” Dylan remembers.
A neighbor’s jack-o’-lantern had been snatched from its porch and viciously smashed on the street, no doubt the work of local teenagers. “I was so freaked out,” Dylan tells me. Dylan rushed back up to his porch and turned the jack-o’-lantern around so it faced the family room’s large window. And Dylan came up with a plan.
That night, Dylan tried his best to secretly stay awake. He lay in his bed on his Batman sheets and thought about his defenseless pumpkin waiting outside for him. When Dylan thought his mother was asleep, it was time to put his plan into action.
Little Dylan slowly got out of bed and crept into the hallway. He could hear his mother’s snore coming from the far bedroom. Down the steps he went, avoiding all the secret spots on the staircase that creaked, a knowledge gained through trial and error and spankings.
At the bottom of the steps, Dylan almost changed his mind. The downstairs was a different planet after bedtime. A deep, impenetrable darkness suffused what was usually so familiar, so warm to Dylan. It seemed a black sheet had been thrown over what made up most of Dylan’s world.
“I closed my eyes and ran for it,” Dylan recalls, “until I hit the couch.” And there Dylan had planned to wait until morning, watching over his vulnerable jack-o’-lantern.
The couch was deep and warm, and Dylan wrapped himself in the blanket that his mother kept there. Determined to spend the night staring at the flickering face of his jack-o’-lantern, Dylan quickly fell asleep.
“I don’t know how long I was out for,” Dylan says. “It was the wind that woke me up.” A fierce storm was on the way – the first of October – and the wind was howling ‘round the house.
Dylan looked out the window, past the pumpkin’s still-glowing smile, but the leaf-littered street seemed darker now as if the storm were blowing an inky blackness over Dylan’s neighborhood. He shuddered a little to think of the cold and the dark just beyond the thin pane of glass.
As Dylan studied the night half-asleep, he thought he caught sight of something else blowing in the wind. A piece of black cloth seemed to be caught somewhere on the sidewalk, maybe on a bush or a lamppost.
“I was concentrating on looking at this thing in the wind,” Dylan tells me, “that I didn’t notice when it started moving closer to the house.”
Dylan could see now that the dark cloth was not moving with the wind; it seemed to form a whirlwind of tattered black fabric that was heading for his house. “Then all of a sudden,” Dylan remembers, “it was standing there in the front yard.”
What looked to Dylan like a mass of cloth one moment was suddenly in the shape of a human figure the next. And it was walking swiftly toward Dylan’s house, toward the window where Dylan sat.
It walked up the porch steps and stopped, the wind seemingly blowing right through it. It wore a great black cloak, shredded and trailing stray strips of cloth. The face was hidden in a deep hood but Dylan sensed a menacing presence there, one he thought he recognized.
“I don’t know if I knew the name at the time,” Dylan says, “but it was pretty much the Grim Reaper on the porch.”
The figure moved closer to the window where Dylan sat frozen in fear, his jack-o’-lantern still stupidly grinning. The figure paused again and it seemed to contemplate the mutilated gourd before it.
Now the figure stood directly in front of Dylan, just behind the pumpkin. It bent over and two bony, clawed hands reached out for the jack-o’-lantern.
Dylan’s pumpkin rose in the air as the figure lifted it high, then it placed the lit pumpkin in the hood, in the spot where its own head should be. The pumpkin sat there awkwardly for a moment as something inscrutable adjusted itself.
In that moment Dylan’s jack-o’-lantern no longer belonged to him. The pumpkin face contorted and stretched, the mouth opened and closed as the eyes squinted in terrorizing displays of dexterity unknown to winter squash.
A great peal of sinister laughter erupted from the pumpkin-headed shadow and joined the wind’s screeching. Dylan could do nothing but watch as the shadowy figure turned to leave. As it did the jack-o’-lantern seemed to look in his direction and Dylan thought it he saw it wink.
Dylan’s mother found him the next morning asleep on the couch. “She searched the whole house before she heard me snoring,” Dylan remembers.
In the years that followed, Dylan made many more pumpkins, but he never forgot his first and the strange fate that befell it. “At first I thought maybe the Grim Reaper took my pumpkin for a Halloween mask,” Dylan tells me. “But now I think it was Samhain, the spirit of Halloween, and he picked my jack-o’-lantern for his head that year.”