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D&D Halloween One Shots Ideas – Jack-o-Lanterns – Halloween Quest ideas

A symbol of tradition is the Jack-o-Lantern. Carved from beets or pumpkins, the twisted smiles and eyes of a Jack-o-Lantern are a spooky lantern that illuminates a holiday wrapped in horror, mystique, and spine-chilling encounters. Do you plan on running a Halloween one shot for Dungeons and Dragons™, Call of Cthulu™, or other table top role playing game? Let the Wally DM YouTube Community help you out. Here is a list of ideas that can help inspire your next spooktacular Halloween adventure!

The fifteenth video in this series is One Shot / Quest Ideas: Jack-o-Lantern Edition. Several ideas are presented below by friends of the Wally DM YouTube Community, but five of them were selected to be presented in this video. Watch the video for full details and find out the popular ideas from those listed below.

D&D Halloween One Shot Ideas – Jack-o-Lantern Edition



Racojah the Loxodon writes:
A green hag uses the pumpkins in her pumpkin patch maze to seal the souls of villagers lost in the maze, turning them into jack o’lanturns. The bodies of the soulless villagers turn into scarecrows scaring off potential victims, however they are only trying to help them through the maze.

Thomas Ison writes:
A mysterious tower made of what looks like giant pumpkins stacked on each other appears in the middle of a town and every night an catchy and enchanted tune emanates from the tower and all those who hear it are compelled to dance until sunrise.
In order to stop the music and give the village a night of rest, you must ride the elevator to the top of the tower and defeat David S Pumpkins and his two dancing skeleton companions.

Twigg writes:
The cult of Jack trying to turn an entire town into Jack O Lanterns with a magical ritual. Idk it just sounds cool haha

Joan Dudley writes:
An evil fey stole a prized seed or gourd from a good fey’s court. This gourd/pumpkin holds tremendous power. Perhaps it’s a rare magical component. She demands the party retrieve it for her.

RIVERS RPG Channel writes:
A necromancer is raising the dead, but instead of heads they have jack o lanterns on their shoulders. These things are harder to destroy and stronger than regular undead.





Cole Bordi writes:
Nestlebrook is a quaint little village that every year hosts a large pumpkin growing competition, to which all the farmers from all the nearby villages compete in. Much to everyone’s surprise, the pumpkins are growing WAY bigger than ever before, which everyone thinks is a good thing… at first…

Dr. Feargood writes:
The adventures have been hired to deliver a package to the hermit at the edge of town; the box reads, “From mother with love, I hope this provides you security.” The hermit grows the grandest pumpkins but never sells any to the townsfolk, but all seem gone after all hallows eve. The adventures can’t help themselves and open the box, only to discover a blue blanket.

Joan Dudley writes:
The legend of Stingy Jack. After playing a trick on the devil, He sent Jack off into the dark night with only a burning coal to light his way. Jack put the coal into a carved-out turnip and has been roaming the Earth with ever since. The PC’s must find the lantern and guide Jack to rest.

Joan Dudley writes:
An NPC is competing in a pumpkin sizing/pie competition. Not wanting to loose, they got a seed from a strange person. When planted, it sprouts into a giant flesh eating pumpkin monster! Is the party too occu-PIED to help? (I had too)

Heartless Nobody writes:
The Headless Lich: Powerful champions have been found dead around the area with a carved pumpkin where their head should be. If investigated, the party will find that it leads to an abandoned field where a Lich is using the heads as replacements for his own, gaining the champion’s abilities when he wears them.

Joan Dudley writes:
Every year, the village lights a pumpkin lantern with an enchanted wand. Someone has stolen the wand. Without the protective ward flame to keep it at bay, the pumpkin flame skull will arise once more.





mark goetzinger writes:
The magical ember/coal used to animate the great pumpkin for the fall festival has been stolen. Possibly a lich or some other dark caster wants to use the coal to animate an army of golems to cause havoc.

Joan Dudley writes:
The new shop in town has a number of masks for sale, which is perfect for a masquerade ball the PCs are invited too. The Lord of the town, and all the guests put on cursed masks and transform into pumpkin monsters! Who cursed them? And why?

Hellbound16
While traveling, adventurers find themselves walking through a pumpkin patch. It seems straightforward enough until one of the vines grabs a leg and suddenly the team finds themselves in an underground maze, maybe some sort of trick designed by a fare. To get out they’ll need to solve a puzzle involving the light of a Jack-o-lantern, carve the keyhole into a pumpkin shaped door, and maybe fight through some pumpkin spice monsters.

Joan Dudley writes:
Ever year the village makes an offering to the headless horseman that haunts a graveyard. This year, someone has stolen the pumpkin that rests atop his grave (that never seems to wilt). The party better find it and fast, before the horsemen seeks revenge…

InquisitorThorn writes:
A desperate farmer made a deal with a hag: every night, his pumpkin patch triples in size. Now the town is overrun with thick vines and the PCs have to stop the hag before it’s too late.

Spencer Bryan writes:
The great pumpkin(g), a new Patron, has unleashed his warlocks to track down Jack O Laneren, a Reborn cavalier. Players discover facts and choose a side.





Joan Dudley writes:
A friendly flame spirit approaches the party, but it is small and dying. It must return to its vessel (a pumpkin) before sun up or perish. It’s vessel has been stolen, and village kids are also smashing pumpkins. If the vessel is broken, it will also die! It will reward the PCs for helping it, but can they do so in time?

Jesse Wyer writes:
Every year the Hollowtide festival is interrupted by Sweetwater Jack, whose light burns only so long as he can fuel it, and his love awaits somewhere in the Maiden’s Mire. End him or help him, but break the curse or he’ll be back next year.

No Fun Allowed writes:
Every night, a townsperson goes missing. Every night, a new scarecrow with a Jack o’ Lantern head appears…..

David Rose writes:
Townsfolk go missing each Autumn as an evil wizard turns townsfolk into pumpkins. Tomorrow is the end of season fair and your group has been picked to judge the best pumpkin pie.

Angelica Garcia writes:
A town worships a pumpkin, which blesses the town. One day the pumpkin is destroyed, the pieces scatter, and the town starts to go to ruin. FIND THE PUMPKIN PIECES!

Marc Accardi writes:
Charlie Brown and the Peanuts gang has to stop Sam Hein and his evil cohorts from raising the Great (old one) pumpkin or release hell on earth.

Chaos Commentary writes:
A small village in the middle of nowhere has been having towns people disappear when they try to leave town and when you go into the pumpkin patch you find a jack o lantern with the face of the missing person





Cheeseburger Dave writes:
Oh Jack was a miserable old drunk who took pleasure in playing tricks on just about everyone: family, friends, his mother and even the Devil himself. One day, he was at his favorite fishing hole when he seen a old house in the woods.He was hungry and decided to see id he could get a sandwich from the old lady in the window.The old lady offered to make Jack a drink and sandwich exchange for his soul. The lady transformed herself into a coin to pay for the food. But, Jack stole the coin and put it in his pocket where he kept a cross. The cross kept the lady from changing back. Jack freed the ole lady, only after she agreed to wait before taking his soul.

Years later, he ran into the lady by an apple tree. The lady wanted to take his soul right then and there. Jack bought some time, by asking the lady to climb up the tree and get him an apple. As soon as the lady was in the tree,Jack trapped the lady by placing crosses in a circle around the tree. Then, Jack made the lady promise not to take his soul when he died. But instead turn him into a jack-o’-lantern for eternity.
The lady was Baba Yaga


That’s all today! Be sure you subscribe to the Wally DM Youtube Channel and keep your eye on the COMMUNITY Tab if you would like to see your name and idea in a future Wally DM one shot ideas video!

On to the next!
—wallydm

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