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Weekly Spooky
Weekly Spooky
Scary stories, urban legends, haunted places, cryptids and dark folklore with Henrique Couto. New nightmares throughout the week. Halloween all year long.
Oct. 1, 2026

Stingy Jack: The Halloween Legend Behind the Jack-o'-Lantern | Thursday Thrills

Stingy Jack: The Halloween Legend Behind the Jack-o'-Lantern | Thursday Thrills

Stingy Jack and the Halloween legend behind the jack-o'-lantern welcome October with a bargain gone wrong. Henrique Couto follows an Irish folktale from a coin trapped beside a silver cross to the Devil stranded in a tree—and a promise with a terrible catch. Discover the carved turnip lanterns once used to frighten passersby, and the dark folklore behind that familiar pumpkin grin. What happens when outsmarting the Devil leaves you with nowhere to go? Light your first pumpkin and join Thursday Thrills for Halloween folklore, mischievous scares and a little light against the dark.

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Story submissions: WeeklySpooky@gmail.com

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There's a particular pleasure in lighting the first jack-o'-lantern of October.

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You lower the light inside, replace the lid, and step back. Suddenly,

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the face you spent twenty minutes meticulously and carefully carving

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looks like it knows something. Behind you, the house is warm.

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There's candy on the counter. A horror movie is waiting.

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But beyond the porch, the wind is moving through the leaves,

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and the light only reaches so far. Tonight, let's follow

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an old Irish legend out past that last patch of orange.

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Somewhere in its darkness walks a man with a little lantern.

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He's beaten the devil more than once before. and he

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would give almost anything for a door that would let

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him in. This is Thursday Thrills, a quick weekly ride

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into the creepy stories, haunted places, weird obsessions, and eerie

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little corners of the world worth talking about. I'm Enrique Couto,

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and tonight we're welcoming October with Stingy Jack, the troublemaker

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whose legend haunts the jack-o'-lantern itself. How does a man

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clever enough to outwit the devil end up carrying a

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light through the darkness forever? Get cozy. This one deserves

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the good Halloween candy. I love the moment when a

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neighborhood starts putting on its Halloween face. A perfectly respectable

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lawn acquires a graveyard. A skeleton takes possession of a

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porch chair. Somebody hangs a ghost in a tree. And

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suddenly a sheet has a more exciting social life than

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the rest of us. You can be coming home from

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a thoroughly ordinary day, thinking about dinner, and there it is.

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The first orange grin looking back from somebody's steps. That

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little face makes a promise. There's still fun to be

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had after dark. Part of the joy is having the

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whole month ahead of you. the candy hasn't all mysteriously

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disappeared yet. The decorations are coming out of their boxes,

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including the one that activates while you're carrying it downstairs

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and nearly sends you through the ceiling. You've got time

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for another ghost story, another night with the lights turned low.

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We're right at the beginning of all of that, and I,

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for one, intend to enjoy it. And carving one is

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half the pleasure. The lid comes off. The seeds go everywhere.

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You attempt a sinister expression and discover you've made a

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pumpkin that looks about its interest rate on the mortgage.

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Put a light inside anyway. Darkness is a very forgiving

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special effects department. But before we give Jack his familiar

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orange face, we should probably meet him. This is folklore,

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with different tricks and bargains depending on who tells it.

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Tonight we're following the version with a coin, a tree,

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and a man who really should have known when to quit.

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The story begins with Jack inviting the devils. for a drink.

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Already the evening has taken a turn. Most of us

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would at least want somebody to know where we were

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just as a backup. Jack has a problem with paying.

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His solution, according to the tale, is to persuade the

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devil to become a coin so he can settle the bill. Now,

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pause there. You're sitting opposite the devil, and your concern

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is whether this evening is going to cost you money.

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That is a remarkable commitment to being miserly. The devil obliges.

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For a moment, the terrible visitor is small enough to

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fit in Jack's hand. Here's how I'd want you to

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see this part. Stay close. Stay close to that hand.

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We know what the coin really is. We know it's

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supposed to be payment. Now watch where Jack puts it.

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Straight into his own pocket. But beside a silver cross.

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In the tail, that cross prevents the devil from changing back.

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Jack has him. All that power tucked away where a

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man might keep a receipt or a forgotten breath mint.

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And for the first time in the encounter, getting out

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is the devil's problem. Jack can set the price. You

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can almost enjoy the triumph along with him until you

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remember what has to happen next. And eventually... He has

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to let it out. The coin trick buys him a reprieve.

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The length and terms shift between tellings, but Jack gets

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more time and the devil gets his freedom. I love

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Jack so much at this stage. I wouldn't lend him $ 20.

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I would absolutely listen to what happened to him on

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the way home. There's a delicious Halloween feeling to a

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story like this. The monster can be enormous, ancient, powerful,

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and still step straight into a trap. You get to

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laugh while the dangerous thing is contained, a little like

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watching a horror movie from the couch with your feet

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tucked safely under the blanket. For so long, eventually somebody

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has to walk down the dark hallway. For Jack, the

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reprieve comes to an end. The devil returns and Jack

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finds another ordinary object to put between himself and eternity.

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This time, it's a tree. In the familiar telling, Jack

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gets the devil to climb up for a piece of fruit.

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Then he marks the trunk with a cross, trapping his

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visitor in the branches. The devil has gone from collecting

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souls to fetching snacks. Jack is getting a lot out

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of this arrangement. But here we are. Jack stands below.

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The devil is overhead. Between them is a mark in

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the bark that, in the rules of this tale, cannot

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be crossed. As a filmmaker, I love how little you

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need to make that image uncomfortable. Put a person beneath

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a tree, let us know there's something up there, then

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hold the shot long enough that we start searching the

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branches ourselves. Try carrying that thought on your next... October stroll.

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You pass beneath a tree every day. You know where

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its roots have lifted up the sidewalk, but when did

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you last look all the way up? Apparently, Jack does,

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and fortunately for Jack, he has the upper hand again.

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In versions where this is his final bargain, he makes

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the devil promise never To take his soul into hell.

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There it is. The big victory. You almost want to

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applaud the awful little man. He's used a pocket and

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a tree to negotiate his way out of damnation. But

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listen carefully to what he's won. The devil cannot take him.

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That doesn't mean anybody else can. Has to. If you're

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enjoying this little walk into Halloween, follow or subscribe to

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Weekly Spooky for more Thursday thrills, and send this one

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to a friend who already has pumpkins on every available service.

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We have 30 more October nights ahead of us, so

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let's enjoy them as much as possible. Speaking of, a

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little later today, there'll be a brand new Halloween horror

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story for you to enjoy, so stay tuned. Now, Jack

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has one promise from the devil. Eventually, he has to

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find out what it's worth. Jack dies. His tricks have

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bought him time, but they haven't made him immortal. In

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the legend, heaven refuses him because of the life he's led.

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Being clever has not made him kind. Outsmarting the devil

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has not erased something else. So Jack turns toward hell,

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and the devil keeps his word. The bargain holds. Jack

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gets exactly what he demanded and discovers he's arranged to

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be locked outside. I find that much creepier than a

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monster bursting through a door. Here, the door stays closed.

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There's no one left to bargain with on the other side.

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For a moment, take away our comfortable October evening. Take

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away the movie waiting on the television and the kitchen

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light you can switch on whenever the house starts making noises.

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Take away the knowledge that you can go home when

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you've had enough. Leave only the road. The devil gives

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him a burning coal to light his way. Jack puts

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it inside a hollowed-out turnip and carries it into the darkness.

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It's such a small thing after all that bargaining. One ember,

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one makeshift lantern, enough light for the next few steps

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with everything beyond them. still hidden. Follow him for a

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moment in your imagination. The lantern travels low, beside his body.

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It brings one piece of the road into view, then

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abandons it behind him. Raise it, and the darkness seems

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to retreat. Lower it, and the dark comes back. You

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could hold it close enough to see your own fingers

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around it, but you couldn't make it show you where

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you're welcome. There's no friendly window at the end of

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this walk, no voice calling you in before you catch

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a cold. Every time you think the story must reach

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a house, the lantern moves on. Jack has all the

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time he could ever want now. In this telling, that

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wandering figure becomes Jack of the Lantern. Jack-O-Lantern. Get it?

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The name on the smiling thing outside your house belongs

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to somebody who cannot get inside. And a turnip lantern

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has a very different face. The National Museum of Ireland

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has a wonderfully unsettling example. A plaster cast of one

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of these old turnip lanterns. The face has pinched eyes

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and a gaping mouth. It looks less pleased to see

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you than the pumpkin on a greeting card. People really

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did put candles inside carved turnips to frighten their neighbors.

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at Halloween. Galway City Museum describes lanterns placed on walls

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and gates or hanging from trees to startle people passing

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in the dark. Now there's a walk home. You turn

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a corner and a face is glowing at you from

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a place where no face makes any sense. For a

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Halloween version of that moment, give yourself a quietly and

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a lantern hanging from a branch just ahead. Its light

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catches the edge of a gate. Beyond the gate, nothing

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you can make out. You know somebody must have hung

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it there, still. For a second, you might prefer it

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if that somebody came out and said hello. I respect

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the craftsmanship. I would also like whoever put it there

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to come and walk me the rest of the way.

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The pumpkin we know grew out of several autumn customs

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and stories, including these older lantern traditions. There isn't one

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tidy moment when somebody invented every part of what we

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now know as Halloween. Jack's tale is one wonderfully creepy thread,

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in that tangle. And I appreciate that the fun was

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even in there, too. Somebody hollowed out a vegetable, gave

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it a dreadful expression, and waited for a neighbor to notice.

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The equipment has improved. The satisfaction of making your friend

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jump remains very easy to understand. So, there's our October Invitation.

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Get the decorations out. Give that pumpkin an expression. Put

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on the movie you've been saving, even if you know

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exactly when the hand is going to come out from

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under the bed. You're allowed to pull your feet up anyway.

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For us, the pleasure is being able to return from

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the dark. A haunted house exit brings you back to

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your Laughing friends. The credits roll. The porch door opens

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and somebody has made something warm for you to drink.

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Jack's story makes that ordinary welcome feel precious. We can

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borrow his little circle of light, but only for an evening.

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We can enjoy the long shadows it makes across the steps...

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Then head indoors and leave the lantern, watching over the street.

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I'm Enrique Couto, and this has been Thursday Thrills. Happy October,

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my spookies. Drive safe, keep your headlights on, and when

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you pass a little orange light out in the dark,

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take a second look. The pumpkins should stay on the porches.

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Jack's lantern just keeps on moving.

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Come back tomorrow for more fear. Until then, lock your

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doors as if that will help.

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Ha ha ha ha ha ha ha ha!