Halloween and dungeon crawling 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 Night of Fright!, A Night of Fright! 2
- The Haunt, The Haunt 2, The Haunt 3
- Happy Jack’s Funhouse
- The Well in the Woods
- One Night Strahd
- The Spookiest Night Ever
- The Chapel on the Cliffs
- The Witch of Underwillow
- Berdusk Till Dawn
- The Madhouse of Tasha’s Kiss
- Knife to Meet You
- The Haunting of Valentyne Manor
- Banquet of the Damned
- The House of the Midnight Violet
Affiliate Link Disclaimer
Some links in this post are affiliate links, which means I may earn a small commission at no extra cost to you if you click through and make a purchase.
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.
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 (or at the very least leaving them a nice review).
These titles 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.
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
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!
The Haunt, The Haunt 2, and The Haunt 3 (Paid)
Unlock the secrets and drive back the evil from Montarthas Manor
2026 Update Note: The first entry in this series seems to no longer be available, but The Haunt 2 and The Haunt 3 are still going strong. Keeping the original description below, but updated the image and links.
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?!
Happy Jack’s Funhouse (Paid)
Are you brave enough to explore the wonders of Happy Jack’s strange attraction?
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…
The Well in the Woods (Pay What You Want)
The forest is wild, and in its shadows something thrives!
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?
One Night Strahd (Paid)
Just remember, death is rarely the end in Barovia
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.
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.
The Spookiest Night Ever (Pay What You Want)
What happens when a group of intoxicated adventurers find themselves in the domains of dread?
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.
The Chapel on the Cliffs (Paid)
It’s been fifty years since the curse struck Kennmouth. Are you brave enough to face it?
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?
The Witch of Underwillow (Paid)
What dark fate awaits the adventurers who face 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?
Berdusk Till Dawn (Pay What You Want)
Berdusk is haunted and is now a ghost town… metaphorically and literally
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.
The Madhouse of Tasha’s Kiss (Paid)
Can you survive the Madhouse of Tasha’s Kiss? Or will you go mad trying?
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?
Knife to Know You (Paid)
Yeah, teens, trust the stranger in the woods. What could possibly go wrong?
Price: $4.95
Length: 3-5 hours
Players: 1-4
Levels: 1st
This one is a bit of a departure from more typical D&D Halloween games, and that’s why I love it for a holiday one-shot. In Knife to Know You from Summerhaven Games, your party plays as teenagers lost in the woods, and their only way out seems to be trusting a mysterious stranger who promises to get them home.
But the woods simply don’t let go that easily.
This is an into adventure into a whole pulp-horror setting called Summerhaven, and the game includes an optional “Teen Pulp” mode that turns them into magic-less characters to really drive home that slasher movie sense of vulnerability at the table.
It’s quick, tense, and the low-magic option makes it feel a lot more true to a horror movie experience perfect for a Halloween game.
In this introductory scenario for the SUMMERHAVEN series of adventures, a group of teenagers lost in the woods are forced to trust a stranger to lead them out safely.
Knife to Know You! began as the teaser chapter for a one-shot adventure currently in development called The Dare House. This quirky little mystery is likely very different from most fifth edition modules you have played, but it still contains all of the elements of a classic adventure. Underneath the veneer of Y.A. pulp horror is the same exploration, discovery, social intrigue, and thrilling combat you love from the world’s greatest roleplaying game.
The Haunting of Valentyne Manor (Paid)
Every hour, on the hour, the manor remembers.
Price: $1.95
Length: 3-5 hours
Players: 4-6
Levels: 1st-4th (Scalable to Higher)
There’s something compelling to me about a haunting that runs on a schedule, and that’s exactly what’s happening in The Haunting of Valentyne Manor by Ryan Loyal Stueve. Seventy years ago, a family was murdered inside of Valentyne Manor, and to this day their deaths replay in grisly detail every hour like clockwork.
Your players aren’t just there to fight off restless spirits, tasked with piecing together what happened and find a way to break the cycle before they’re pulled into it themselves.
Over seventy years ago Valentyne Manor bore witness to a horrible atrocity. A curse hangs over the site where a family was torn apart. Every hour their murders are played out by tormented spirits in a macabre exhibition. Can your heroes solve the manor’s riddle or will they be doomed to join the ghostly procession?
Banquet of the Damned (Paid)
Can you survive the Madhouse of Tasha’s Kiss? Or will you go mad trying?
Price: $3.95
Length: 4-6 hours
Players: 3-6
Levels: 4th
There’s something so creepy about a genuinely sinister situation hiding behind something nice and wholesome. In Banquet of the Damned by Benoit de Bernardy, a farming village’s annual pie contest feels about as wholesome as it could be. Pastoral. Pleasant. Quaint, even.
So of course there’s an ancient evil lurking underneath it all, using the village and its bounty for its own ends. The adventure offers strong vibes of Midsommar or The Wicker Man.
An ancient evil lurks in the shadows of Womford. While everybody is getting ready for the annual pie contest, a vile creature is carefully preparing its next move. It’s only a matter of time before it wrests control of the gluttonous swine of Womford. Will your PCs stop it before it’s too late?
House of the Midnight Violet (Paid)
A simple quest to fetch some flowers… from a mansion nobody wants you to enter
Price: $6.95
Length: 3+ hours
Players: 4-5
Levels: 4th-6th (Scales up to 12th)
The premise of House of the Midnight Violet by Jeff C. Stevens is deceptively simple: the party is hired to recover a rare flower from an old mansion. The townsfolk warn the party off, which of course just makes the job that much more appealing.
Players will discover a tragic family history buried in the walls of a spooky manor, encounter unique creatures made just for this module, and make their way through a unique horror experience.
The level range for this one goes all the way from 4th to 12th, so players in a wide spectrum can hunt for the Midnight Violet and have a challenging, creepy time doing so.
The party is recruited by an innkeeper to recover a flower from a nearby mansion. He is an alchemist and he is running short on his supply of the Midnight Violet.
Town rumors warn the party to stay away. But, that’s unlikely given that your heros are mighty and brave.
While exploring the mansion, the adventurers will learn the story of the family that once lived there and what caused their demise. That is…if they live that long.
Graycastle Press is Luke Miller
Building games, homebrew, modules, and digital tools for the tabletop community and beyond with a unique brand of creativity and sense of humor. Publisher of the bestselling solo worldbuilding roleplaying game Journey.
Specializing in games that offer new methods of engaging with your creative work. Go on an adventure and return with the choicest loot: fresh ideas and inspiration. Use it to add even more spark to the things you build.