Halloween D&D Adventure

D&D Halloween Adventure with Vampires and Werewolves.

The Hook:

Word has reached you from a nearby village that the new owner of the keep is a vampire and the castle grounds are guarded by werewolves. The next full moon is only three days away and the village elders fear things may get ulgy.

The mayor promises 100 gold pieces and the town will support the party’s claim on the keep if the adventures can rid them of the vampire and his minions.

DM Notes:

The villagers are right about almost everything. The new lord of the keep and his family are vampires and their guards are werewolves. The villagers are wrong in one very important way; they are in no danger from the new occupants of the keep.

For a more roleplay-heavy game, use the locations/NPC content below to allow players to explore the town and gather clues and rumors.

If your group is more combat-oriented, they can try to infiltrate the castle grounds and the castle itself. The werewolf guards will use psychological warfare, hit-and-run as well as pack tactics against the PCs. Their goal is to scare off invaders rather than kill them. 

When the players manage to get into the castle, SURPRISE! It’s a haunted house adventure! Landry Chaperone and her personal bodyguard will know when and where the party enters the castle. They will start to play a game of cat and mouse with the PCs.

Landry is bored easily and a group of PCs is the perfect way to break the boredom. 

Lord & Lady Chaperone

Chaperone-vampire-family-portraitThe Chaperone family were cursed to be Vampires by a vengeful and jealous lord many generations ago. Since then the family has not only learned to live, but thrive with the curse. Not having been turned by a vampire, they retain their personalities and good alignments.

Landry Chaperone, the daughter of Lord & Lady Chaperone, may look like a young girl, but do not be fooled. She is hundreds of years old and fully capable of defending herself. She is highly intelligent and a skilled wizard specializing in the subtle casting of illusions. 

Over the years the Lord and Lady, along with their daughter, have made many powerful allies and work in the shadows to improve their world in many ways. 

Plot Points

  • The Chaperones have come to this small, backwater keep because they suspect a dark evil has risen from the swamps. Their network of informants has reported many strange and disturbing events in nearby areas pointing to this small town as the possible headquarters of a rising evil.
  • The Chaperone family prides themselves on the fact that they do not feed on humans, nor do they kill their food. In point of fact, they have allied with a pack of Warewolves that they can feed on without the worry of spreading their curse.
  • More than anything else in the world, Landry Chaperone wants a companion; one that sees and accepts her for what she is.
  • Vasily Borz, captain of the guard and alpha werewolf keeps his pack disciplined and well-ordered.
  • As elder werewolves, the pack retains their human minds and military discipline. Any that are not able to do this are culled from the pack.
  • There is fierce loyalty between the Chaperone family and their loyal guard. 
  • In addition to their loyal guard, the Chaperones employ Twig Blights to guard the castle grounds.

The Samp: A Rising Evil

For our table, I used this adventure as a way to introduce the Sunless Citadel from the Tales from the Yawning Portal. There are many other adventures that center around evil rising from the swamps, so feel free to link this adventure to any of those or one of your own.


Thomas Darkdraft – Shopkeeper (Darkdraft’s Sundries)
Physical: Thomas is a 41 year old male human shop keeper. He has a bald head and gray eyes. He has soft brown skin. He stands 177cm (5’9″) tall and has an overweight build.
He has a round, stunning face with a long van dyke beard.He is very nimble.

Personality: He always has time to help others, as long as there is a coin in it for him. He shows very little empathy towards others. He judges people by their actions, not their words. He stretches the truth to tell a good story.

Secret: He has around a large purple egg of unknown origin.

Winifred Farlight – Baker (Winnies’ Bakery)
Physical: Winifred is a 20 year old female human baker. She has long, curled, brown hair and brown eyes. She has rough, pockmarked, golden skin. She stands 177cm (5’9″) tall and has a massive build. She has a jolly round face.  She has a small scar on her right arm.

Personality: Winnie, as the townsfolk call her, is jovial and engaging. She is eager to please. She is always one to swap stories, the juicier the better. 

Secret: She is being blackmailed and would do anything to get rid of her blackmailer. 

Roger Rowntree – Smith (The Forge)
Physical: Roger is a 59 year old male human smith. He has short, straight, red hair and green eyes. He has rugged brown skin. He stands 149cm (4’10”) tall and has a muscular build. He has an edgy, creepy face. He is slightly allergic to tieflings.

Personality: He will always prioritize the needs of other people, even to his detriment. He is very pessimistic. He enjoys tavern brawls. He sporadically misquotes common sayings and mixes metaphors (i.e. “I’ll be with ya in two shakes of a dead frog’s hair.”

Secret: He receives regular payments from an unknown source for spying on the villagers and reporting on local events.

Gorvena Caskbow – Innkeeper (The Lucky Pelican) 
Physical: Gorvenal is a 20 year old female human innkeeper. She has very long, wavy, brown hair, black eyes, and golden skin. She stands 187cm (6’1″) tall and has a round build with a square, plump face. She is heavily allergic to strawberries.

Personality:  She is loud and boisterous. She is very cynical and materialistic. She uses a beautiful walking cane, more for show than need. She has a crude sense of humor.

Secret:  She is part of a secret rebellious organization that wants to take control of the government.

Tristan Keenseeker – Merchant (Keenseeker’s)
Physical: Tristian is a 65 year old male human merchant. He has very long, wavy, brown hair and blue eyes. He has rugged, pockmarked, dark skin. He stands 164cm (5’4″) tall and has a muscular build. He has an edgy, attractive face with a long van dyke beard. He smokes the pipe sporadically.

Personality:  He easily holds grudges. He is generous and quick to strike a deal. He cannot tolerate rough living conditions. He doesn’t like being told what to do.

Secret: He needs help sabotaging a drinking competition.

Rumors and Clues

The new lord of the castle is a vampire. I hear he is raising a little girl in the castle. Probably a snack for later.

Boys down at the docs have been talking about how they been see’n werewolves prowl’n in the swamp. You can hear em’ howl’n at night.

Frog hunt’n and fish’n ‘s been pretty bad lately. Somth’n ‘s out in that swamp eat’n ’em all up. 

A creeping fog clings to the ground surrounding the castle for several hundred feet. The fog occasionally takes eerie forms, like grasping claws and writhing serpents.

All the plants in the vicinity of the castle have died. Dead trees dot the landscape. Only twig blights survive along the castle walls and grounds.

There’s been some strange come’ns and go’ns ’round here lately. More than one of the townsfolks ‘ave gone miss’n. Some say they moved out in the middle of the night, but I think they were lured up to that castle, and ain’t nobody ever gonna hear from ’em again.

I seen the the blacksmith talk’n to a raven the other day. Hold’n a full-fledged conversation. It ain’t natural. 

Ol’ Pinker and his kid swear they saw the ruins of a castle just stick’n out of the ground. He said they was check’n out a sinkhole that opened up when they found it. Last I heard, they was head’n out to see if they could get in and do a little explor’n. Maybe come back rich.

There’s been a lot of bats round lately. Some say it’s ’cause of the the new Lord is a vamp, but I say bring ’em on! I haven’t been bit by a mosquito in over a month.

I don’t know what they are eating up there in that castle, but whatever it is, it ain’t coming from our market. We ain’t seen no visitor from up there since they moved in. Seems a bit suspicious to me.

Swamp Random Encounters

1d8+1d12Swamp Levels 1-4
21 giant crocodile
31d2 will-o’-wisps
42d4 mud mephits
(using dust mephit stats)
51 ochre jelly
63d6 bandits
71 green hag
81d4 Giant Spiders
9-111d3 Warewolf Guards/Scouts
12-132d4 twig blights
141d4 giant toads
152d4 poisonous snakes
161d4 swarms of insects 
171d4+1 kobolds with 2d4 giant toads
181d6 crocodiles
191d2 Swarm of Bats
201d6 giant poisonous snakes

Source: https://www.randroll.com/table/table-rolls-5e-swamp-encounters/
Additional, higher-level encounters are available here.

1d8+1d12 Probabilities:


9-11 = 24.99%
12-13 =  17.32%

Cat & Mouse with Landry Chaperone

Depending on how large the party is and how intimidating they look, Landry will use one of the following tactics to engage the party.

  • Party is very powerful – Landry will play the victim. She will use tactics like sitting on the floor holding her doll and crying or come running down the hall screaming like she is being chased.  Once she convinces the party to protect her from the “big bad evil” haunting or chasing her, she will use Subtle Spell to cast low-level illusions and lead the party on a merry chase through the castle.
  • Party is a moderate threat – Landry will engage the party from a distance, calling to them from down a long hall or using Message or a Minor Illusion throw her voice. She will hide in the shadows and the many nooks and crannies of the castle. If the party is aggressive, she will leed them on a chase through the castle.
  • Party is a minor threat – Landry will use her telepathic bond with her bodyguard and the two of them will chase and party around the castle.

Landry’s goals are simple, scare the party, get a good laugh, and run them until they drop from exhaustion. See the rules for running a chase here.

Regardless of which version of cat & mouse Landry chooses to play, the fun will come to an abrupt end if the party actually harms the girl. In that event, she will summon her bodyguard telepathically and he will alert the rest of the castle. This will bring all of the castle guards as well as the Lord and Lady Chaperone. 

Landry is a Wizard and will use her casting abilities to make the game more fun in the following ways:

  • Subtle Spell – Long ago Landry learned to use this meta magic. Now she can use it at will and does not need to upcast spells in order to use this effect. When in the presence of the party Landry will use this ability to hide her spellcasting.
  • Minor Illusion – Landry will use this cantrip to create sites and sounds that will help push the party in the direction she wants them to go. If she sees there is a wizard in the party, she will tend to creating sounds so there is little to no chance that they will be detected as illusions. She may also use this spell to hide doors or entire hallways behind the illusion of a wall.
  • Mage Hand & Unseen Servant – Landry will open & close doors, move furniture & drapes, bunch up carpets to trip people, and generally cause distractions using one or both of these spells. 
  • Message – Landry will subtly manipulate party members using Message. From simple distractions to jumpscare tactics, she will use this cantrip to drive party members to the brink of insanity.
  • Thunderclap – In the event, she is cornered or feels like she is in real danger, Landry may use this cantrip as both a distraction and a way to call for help. Upscale the damage based on the level of the party.
  • Mold Earth – Landry will move stones in the floor just enough to create a tripping hazard. Consider this as creating difficult terrain and call for dexterity checks to see if characters fall prone (trip).
  • Misty Step – Landry will retreat from danger using a combination of her preternatural speed and Misty Step.
  • Fog Cloud – What’s more creepy than an old dark castle at night? An old dark castle with a cloud of fog rolling down the hallway, completely obscuring your vision. Landry will use this to guide, scare or slow down the party.

The End is Just the Begining...

Once Landry has finished playing with the PC’s, they will be brought to meet the Lord and Lady of the castle. Lord Chaperone will explain to the party that they are no threat to the neighboring villages, but there is a real and growing danger. Here is your chance to introduce the next adventure or even have the party put on the payroll of the Chaperone family.

Feel free to use the Chaperones as quest givers, recurring competition, or even the occasional information source for the party when they need one. 

If your party chooses to hunt and kill the Chaperone family and their guards, the local townsfolk will live up to their promises; however, the Chaperones have many powerful friends and there is a growing menace that will need to be dealt with sooner or later.


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