13+ Spooky One-Shots for Spine Chilling D&D Halloween Adventures

There’s just something about the fabled holiday special one-shot, but even more so when it comes to the spookiest of the holidays. Halloween and dungeon crawling just go so well together, and putting together a memorable game for your group to commemorate the season of pumpkins and candy (and I guess scary things too) can be a really fun experience both as a dungeon master and player.

Luckily there are so many fantastic adventures available that can make planning, prepping and executing a truly memorable (and truly limited to one session) one-shot for the upcoming holiday that have a variety of levels of spooky vibes and creepy thrills. 

A Note About Pay What You Want (PWYW) Titles

You’ll note a number of titles in this list that are listed as Pay What You Want, and if you haven’t spent much time on DM’s Guild or DriveThruRPG, that might be new to you. Even so, it’s pretty much what it says on the box: you can choose the price at which you’d like to purchase that product (even if that price is $0). They will often have a recommended price listed, but you can change that value to what works best for you and your budget.

If your budget doesn’t allow you to spend on adventures, these PWYW titles can be a really nice way to pick up content for cheap or free. However, I always recommend revisiting the titles you ended up loving and getting a lot of value that you picked up for free and buying them again. 

These adventures and supplements often take a lot of time, work, and money to produce and distribute, and supporting creators just helps ensure they get value in return and are able to keep making awesome stuff for the community.

What paid and pay what you want one-shot adventures can I use at my table for a D&D Halloween special?

The list below contain a variety of really fantastic adventures perfect for your table’s Halloween one-shot in no particular order. You’ll be ready to scare the socks out of your players in no time, and even with some free options for the budget-conscious table!

One Night Strahd (Paid)

Just remember, death is rarely the end in Barovia

Cover image of One Night Strahd
Cover image of One Night Strahd

Price: $18.00
Length: 16 hours
Levels: 6th

The whole Curse of Strahd adventure is one that I’ve wanted to take part in since before I even started playing D&D. Entering this dark region shrouded in mystery and facing horrific challenges, betrayals, and sinister secrets just really appeals to me.

But man, it’s a long adventure.

I’ve heard various numbers quoted for how many hours Strahd takes to run on average, with around 200 hours being the most common number I’ve heard.

What if you could condense all of the horrific action of the Curse of Strahd adventure into 12 or 16 hours? That’s the bold claim on One Night Strahd, which I’m currently working on talking someone in my gaming group to run for us because man, I really want to play.

The art style of the book is bold and cool, the idea of a fast-paced dash through Barovia is super appealing as I begin turning more and more towards short / one-shot games, and the description of the adventure really just sounds up my alley.

Beautiful artwork from One Night Strahd
Beautiful artwork from One Night Strahd

One note, though, the description notes that you can expect to get through One Night Strahd in about 12-16 hours of play depending on which format option you choose, which unless you’re planning a truly epic overnight game for the spookiest of seasons, might take you more than one night to get through. Sure, it’s not technically a one-shot, but it could be, and my heart wants it to be, and it’s just so pretty.

Precise and messy as a vampire bite, One Night Strahd (ONS) delivers the spectacle and catastrophe of gothic horror as a consistent and fast-paced short campaign for D&D 5e. It condenses and remixes the 200+ hour campaign of Curse of Strahd into a replayable adventure weighing in at 525 pages with 150+ illustrations, 12 maps, 16 encounters, 27 new magic items, and 60+ quick-play charts. With careful attention to the design of exploration, combat, and role-playing opportunities, our goal has been to make something for every DM and every table. After three years of extensive testing, we’re proud to share this explosive adventure with you.

Available in Digital and Paperback on DM’s Guild

The Haunt, The Haunt 2, and The Haunt 3 (Paid)

Unlock the secrets and drive back the evil from Montarthas Manor

Cover image for the D&D Adventure The Haunt by P.B. Publishing
Cover of The Haunt by P.B. Publishing

Price: $6.95
Length: 6-8 hours
Levels: 4th-5th

I’d hazard a guess that anything that makes it to the level of an Adamantine Bestseller on DM’s Guild is well worth a look, and The Haunt looks like a perfect example.

Besides the physical book looking really beautifully done (it’s also available in PDF format), the adventure sounds like a really spooky, creepy option for a Halloween one-shot.

The adventure lists an expected one-shot run time of 6-8 hours for a party of characters at 4th – 5th level, so it might be a tad long for some tables, but if you’re looking to immerse yourself in a creepy haunted house for a long evening with your friends, The Haunt might be just the ticket.

Best of all, if you end up loving this dark adventure, you can follow it up with Haunt 2 and Haunt 3 from the same author!

In ages past, an ancient town was lost and destroyed to a siege of orcs. Only one building survived and to this day, the manor is the only still standing building to be seen for miles around. Some say it is haunted, a few whisper of great treasures within, whilst others whisper that it is the manor itself that lives!

No one knows for sure, only that a great evil haunts its halls.

Do you dare enter Montarthas Manor?!

The Haunt is Available in Digital and Paperback on DM’s Guild
The Haunt 2 is Available in Digital and Paperback on DM’s Guild
The Haunt 3 is Available in Digital and Paperback on DM’s Guild

The Spookiest Night Ever (Pay What You Want)

What happens when a group of intoxicated adventurers find themselves in the domains of dread?

Cover image of The Spookiest Night Ever
Cover image of The Spookiest Night Ever

Price: PWYW ($3.41)
Levels: 4th-6th

Want to combine the wild blackout shenanigans of The Hangover with the danger and terror of a true halloween adventure? This adventure claims that it does just that, with players being pursued by the horrors of Ravenloft and, most likely, a really wicked hangover.

Your adventures will find themselves trapped in the domains of dread with no recollection of the day before, tasked with settling their debts (or, you know, dying horrifically or never escaping).

“An adventurer always pays their debts.” said no one ever. But what if said adventurer is trapped in the domains of dread, and cannot leave until they settle their debts?

“The Spookiest Night Ever” is not your average hangover story, because nothing is deadlier than Ravenloft; hags, undead and something even worse will challenge your players – will they fight and resist, or die trying?

One thing is sure: this adventure will make them die laughing… in one way or another.

Available in Digital and Paperback on DM’s Guild

The Chapel on the Cliffs (Paid)

It’s been fifty years since the curse struck Kennmouth. Are you brave enough to face it?

Cover image of the D&D Adventure The Chapel on the Cliffs by Joseph Crawford
Cover of The Chapel on the Cliffs by Joseph Crawford

Price: $4.95
Players: 4-5
Levels: 3rd

Another bestseller, and one that’s really well reviewed, The Chapel on the Cliffs looks like a spooky good time.

Some of the reviews for this creepy adventure call it “the best 5e adventure I’ve seen” and that it “surpasses any other adventure I’ve purchased on DriveThruRPG or DMSguild,” so you can likely expect some truly good quality adventuring alongside a spine-chilling adventure.

The adventure comes with lots of great illustrations, custom magic items and monsters, some interesting rules for handling sieges and chases, and even a nice printable DM companion booklet to help you run and scale the adventure as needed.

The Chapel on the Cliffs is a 5th edition horror adventure optimized for a group of 4-5 characters of 3rd level. The module mostly focuses on combat and exploration, but it also offers some interesting roleplaying opportunities to PCs who don’t kill everything on sight.

It’s been fifty years since the curse struck Kennmouth. Since then, few have dared brave the dangers of the abandoned village, but even fewer came back in one piece. Will you be the heroes who finally rid Kennmouth of its denizens?

Available in Digital and Paperback on DriveThruRPG

The Well in the Woods (Pay What You Want)

The forest is wild, and in its shadows something thrives!

Cover image of The Well in the Woods
Cover image of The Well in the Woods

Price: PWYW ($4.00)
Length: 4-6 hours
Levels: 6th

The storyline of an ancient settlement being unexpectedly and suddenly swallowed by a sinister local forest filled with all kinds of known and unknown creepy crawlies sounds like a really fun and exciting way to spend a Halloween evening with an adventuring party. 

Find your way through this dark forest and solve the mystery that caused the old down of Schreckenburg to be lost to the trees!

The village of Schreckenburg is an ancient settlement, having been founded many centuries ago. The neighboring forest, once called the Summer Glades, has since swallowed up the stubborn community, enveloping it within a dense maze of twisted trees and thick shrubs. Many souls have been lost to it, drawn within by its dark beauty and mysterious allure. The forest is wild, and in its shadows something thrives!

Just before winter, the folks of Schreckenburg honor an old tradition to keep the dark spirits of the forest at bay. On Hallow’s Eve they must offer a sacrifice to the Well in the Woods. For centuries, this practice has kept the village safe, and no spirit has invaded the land of mankind. However, this year the Will of the Forest will be tested, for no longer will Schreckenburg families throw away the lives of their children just to appease an entity that doesn’t exist . . . or does it?

Available in Digital and Paperback on DM’s Guild

A Night of Fright! and A Night of Fright! 2, the Lich’s Ghost (Paid)

Join Four Mystery Solving Adventurers and their Talking Gnoll for a Night in a Haunted House

Cover image of A Night of Fright
Cover image of A Night of Fright

Price: $4.95
Length: 4 hours
Players: 5

While there is no lack of spooky and scary content for some of our favorite tabletop games, not everyone is excited about scary things covered in blood and screaming at your character for their brains.

Why not play as some meddling kids, instead?

The two-part A Night of Fright! series does exactly that, plopping four teenaged mystery solvers and a talking gnoll into some wacky hijinks, all in the name of unmasking a ne’er-do-well who is stirring up some trouble. If you haven’t figured out what it’s parodying yet, it rhymes with hootie hoo.

Okay, it’s Scooby Doo for Dungeons & Dragons, and it sounds like a hoot…ie hoo (I just can’t stop myself, y’all).

One of my favorite parts about this silly adventure that seems like more laughter that slaughter is that each of the pre-made characters comes with a fully playable custom subclass that lets you continue your adventures with Mystery, LLC beyond the initial two adventures. 

Play as the Bespectacled Sleuth Rogue, a Warlock of The Damsel, the Oath of Traps Paladin, the Way of the Coward Monk, or everyone’s favorite snack motivated class, the Bardic College of Snacks. They all sound like a lot of fun to play in a silly spooky campaign, and sometimes that’s just what the witch doctor ordered.

A Night of Fright is a parodic one-shot adventure designed to be played in a single four-hour session by five players. In a loving send-up of classic mystery cartoons, players will take the role of one of four meddling heroes—or their talking gnoll! Explore a haunted mansion full of traps, frights, spooks, scares, ghosts, ghasts, and ghouls to uncover old Uldryn’s secrets before it’s too late—for this is no run-of-the-mill real estate scam. There’s real danger in the mansion and Mystery LLC will need all the help they can get! 

A Night of Fright! is Available in Digital and Paperback on DM’s Guild
A Night of Fright 2! is Available in Digital and Paperback on DM’s Guild

The Liching Hour (Pay What You Want)

Fizzbang Frazzlepop has always been a little unhinged…

Cover image of The Litching Hour
Cover image of The Litching Hour

Price: PWYW ($4.99)
Length: 3-5 hours
Players: 4-6
Levels: 3rd-10th

What could be more gloom and doom than the looming summoning of the great and dreadful Vecna in one of D&D’s most well known starting towns, Phandalin? Your party will meet a hapless goblin necromancer-trying-to-become-a-lich. You know, tale as old as time, song as old as rhyme.

Except this goblin’s new “get lich quick” scheme involves summoning Vecna himself.

Send your players on a race against the clock, facing off against hordes of terrifying (and sometimes silly) undead creatures seeking to hinder their progress.

Or maybe you’ll turn the tables on everyone and claim Vecna’s prize yourself? That’s the magic of TTRPGs, folks.

It’s a race against the clock as the party must decide if they want to help or hinder a goblin necromancer’s attempt to summon the archlich Vecna to the town of Phandalin at midnight on Liar’s Night. 

Fizzbang Frazzlepop has always been a little unhinged. He has devoted his life to becoming one of the vilest creatures in the multiverse: a lich.

Unfortunately, despite being a highly intelligent Wizard who studied under the top faculty at Strixhaven’s Witherbloom College, Fizzbang has fallen multiple times into what may best be called “Get Lich Quick Schemes.” He is far from a discerning goblin, and that’s putting it nicely.

This time, however, Fizzbang may have actually found what he’s spent decades looking for. This particular Get Lich Quick Scheme involves contacting the archlich Vecna on Liar’s Night.

Available in Digital and Paperback on DM’s Guild

The Witch of Underwillow (Paid)

What dark fate awaits the adventurers who face the Witch of Underwillow?

Cover image for The Witch of Underwillow
Cover image for The Witch of Underwillow

Price: $1.50
Length: 2 hours
Levels: 1st-3rd

Sometimes faster is better, and this supernatural little module delivers. With an estimated two-hour runtime for a small group, this adventure would be tough even for someone like me to allow to spill over into a second session (though, to be honest, I could probably still manage it).

With a seemingly straightforward story of saving a kidnapped child from a scary forest, despite the possibility of shady dealing and surprise twists, there is a lot of room for this game to have bits and pieces added to it to make it what you and your table want without pushing too far past the original time estimate.

So dust off those witch hunting… gloves? Boots? What piece of clothing is associated with witch hunters? Well, whatever it is, go find yourselves a witch!

The villagers fear the forest, and rightly so. When wolves drag a child into the forest, there is only one option: find brave adventurers to follow the wolves and save the child! However, are there things the villagers aren’t telling the adventurers? What dark fate awaits them when they face the Witch of Underwillow?

Available in Digital and Paperback on DM’s Guild

Berdusk Till Dawn (Pay What You Want)

Berdusk is haunted and is now a ghost town… metaphorically and literally

Cover image of Berdusk til Dawn
Cover image of Berdusk til Dawn

Price: PWYW($0.00)
Length: 4-6 hours
Players: 4-5
Levels: 8th-10th

Trade cities are always hotbeds of illicit and underhanded activity, but something in the city of Berdusk seems to have taken things too far. Find this once bustling city riven by paranoia and fear as a dark corrupting influence spreads across town.

With the adventure taking place inside of a city, this module has a little bit of different flavor than a lot of others on this list and could be a lot of fun!

The adventuring party is en route to the major trade city of Berdusk after Mayor Griffith Hawkins called upon them for assistance. It seems Berdusk is haunted and is now a ghost town, metaphorically and literally. The town has destroyed itself with paranoia, accusing friends and family of being responsible.  

Available in Digital and Paperback on DM’s Guild

Happy Jack’s Funhouse (Paid)

Are you brave enough to explore the wonders of Happy Jack’s strange attraction?

Cover image of Happy Jack's Funhouse
Cover image of Happy Jack’s Funhouse

Price: $6.95
Length: 4-8 hours
Players: 4-6
Levels: 3rd-10th

There are few things scarier than a scary clown (except for a clown that isn’t meant to be scary but still is, oh lord now I’m thinking about clowns) and the cover of this adventure promises some white face paint in your party’s future. Or would it be face… PAIN-t? No? Anyone?

Normally, the circus coming to town is a big to do, an exciting event that everyone will talk about for ages. Happy Jack coming to down seems to be the same, but is everything truly as fun in the funhouse as it seems?

With a good amount of content that can scale with your players over a wide range of levels, great for dropping into an ongoing campaign as a fun and scary one-shot, you’ll have plenty of sights to see inside Happy Jack’s. Ever come face to face with a Werehippo? You’re about to. Just don’t forget to tip the Happy Jack’s Employees that seem to pop up where you least expect them.

The level range alone makes this an intriguing option for group who want to play some Halloween season games, easily able to be dropped into whatever town your heroes find themselves moving through. Even better, this adventure is one a set of three in Jeff Stevens Games’ Freak Show Collection (which includes The Madhouse of Tasha’s Kiss, below).

The painted man rode into town, tossing candy and small trinkets to the cheering children. The children, their mouths stuffed with gumdrops, laughed at his jet-black horse adorned with a white saddle festooned with jingle bells.

He introduced himself to the town elders as Happy Jack and asked their permission to set up his attraction in the town square. The elders, seeing the happiness in the children, agreed.

Happy Jack brought with him food vendors and a thrill ride—a large painted attraction which manifested from a leather green and red checkerboard satchel after he placed it on the ground.

All was fun for two days…

Available in Digital and Paperback on DM’s Guild

The Madhouse of Tasha’s Kiss (Paid)

Can you survive the Madhouse of Tasha’s Kiss? Or will you go mad trying?

Cover image of The Madhouse of Tasha's Kiss
Cover image of The Madhouse of Tasha’s Kiss

Price: $6.95
Length: 3-5 hours
Players: 4-6
Levels: 3rd-10th

Part of the Freak Show Collection from Jeff Stevens Games (which includes Happy Jack’s Funhouse, above), this adventure sees another intriguing side show rolling into town that isn’t quite what it seems. You’ll find a single child remaining in a previously bustling town who points you to a mysterious jester’s wagon that drew everyone in town inside.

With a content warning that notifies potential victi… I mean, players of “grim horror, horrific details, animal humanoids,” you know whatever group of adventurers tries to delve the secrets of the jester’s cart are in for some unpleasant surprises.

A small village, empty of villagers except for one boy found sitting and weeping next to a jester’s pageant wagon. The boy explains that the villagers, including his family, followed a jester into the wagon and never came out.

A portal to a pocket dimension is found inside the wagon, leading to a brass door with the word Madhouse etched into it. What lays beyond the door? What madness could the adventurers face? Can they save the villagers, or will they go mad trying?

Available in Digital and Paperback on DM’s Guild

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