Ahoy, adventurers! As things get spookier outside I like to challenge myself to up the spooky in my fantasy games. And yes, Halloween season is almost over. But I count all the darker, chillier days surrounding the new year as spooky because I secretly run on photosynthesis and think every sunset is another ghost story to me. And now, to take a Vitamin D supplement.

“But Dan,” you might think, “I bet I can alter the course of this article if I think directly at its author.” And you might follow that up with, “Why not settle for standard spooky in Dungeons and Dragons? Your completely optional suggestions frustrate and terrify me. Why ruin a perfectly upbeat, pastel-colored Dungeons and Dragons game by stuffing it with eldritch horrors n’ such?” 

Sidenote: Eldritch Horrors N’ Such is my favorite Halloween resale store. 

Well listen, I’ve been playing D&D for a long time, and surprising players is one of the last ways I can feel something. Better I write this article than finding my fix playing an Elder Scrolls game from over a decade ago, scraping the Morrowwind countryside for one last unsolved sidequest.

Thus I have created another “Nightmare Tavern,” this one a little extra nautical in nature. Because nothing makes you want to drink like a whole bunch of saltwater. Have you tried drinking the ocean? 

Sidenote: Don’t! 

Entering The Porthole

Unassuming but with a warm lantern glow emanating from within, there’s no reason to be suspicious of this place. With a large open drinking area and a series of rooms for let on a second floor, it simply looks like an average rustic seaside place to have a few drinks and with some relatively sane company, hopefully so that things don’t devolve into that Robert Eggers Lighthouse movie. But in its own way, it will.

There will only be a few other weary drinkers when the party enters. Oh yeah, hey party that might be reading this. I wanted to tempt you to read and get stoked with those references, but this might be the point where you wanna link this over to your Dungeon Master and see what they think, ‘cuz here’s where I explain the weird.

With the very first step into the tavern, take note of everyone’s passive perception. If anyone can beat an 18, let them know that a creak from that first footfall on the wooden floor elicits an odd, yawning echo, but further listening should give no further clues. There is an enchantment under the floor to keep things silent down there, which Detect Magic reveals only as a huge, broad aura.

Socializing With The Damned

The Fractured Porthole’s staff aims to please. They are carefully curated nervous wrecks who cannot wait to give you a normal night of relaxation... and possible humanoid sacrifice. Look, I told the players they might want to stop reading. 

It’s customary for everyone there to have a rollicking night out, then head home undrowned! I mean, most of the time. There’s just the small issue of a voracious evil vastness lurking beneath it all.

The bartender, the bard, the server, the doorman, and a regular all collaborate to make a patron drunk, too drunk, and pretend they’re knocked out upstairs sleeping off their woes when in reality they are tumbling into a void. It is recommended that players interact with whichever characters they like in whichever order they prefer, just like in real life! Most customers don’t think much of the staff except that they’re nervous and kinda thirsty. You know, needy thirsty. Plenty to drink here.

The Hole’s Curse

Wow that’s a fun header to write. Though The Fractured Porthole rests next to the docks on a pebble beach, it is closer to briny depths than it may appear from the boardwalk. For only the outer walls rest firmly on the ground; the majority of the tavern hovers over a violent whirlpool reaching deep into another plane. Were one to rip up the floorboards, one would see something not unlike an ocean, silently swirling into an infinite funnel. 

A sacrifice must be made once a day. A sentient being must be dragged to a trap door in the storage room and tossed into the watery abyss. Otherwise the staff will become plagued with maddening nightmares, ones that follow them into their waking hours, pulsing sounds, mysterious whispers, black static in the corners of their vision, you get the idea. They can’t go to barbecues or anything. If they miss a sacrifice, every NPC bound by knowledge of the secret has 1d4 days before they go mad, and are compelled to hurl themselves into The Pit. Some patron has to get drugged and dragged into the storage room, which is attached to the kitchen behind the bar itself, or it’s going to get really Lovecraft up in this place.

Players will not become afflicted by the curse unless they become emotionally attached to the staff and their plight. Even in that case, a basic Wisdom check (Insight) reveals these people are all murderers and probably beyond help. So you know, if they want to throw their character into The Pit and you want to describe what it feels like to be torn apart by a tentacled maw after being thrown into a pitch-black corner of space and time, that’s the final page of that particular Choose Your Own Adventure path. I guess if your characters are all level 20 gods who can fly down through the door and fight a customized Kraken in magical darkness you can stage that too, but that's an article for another Halloween.

On the other end of the dark expanse is some sort of nameless evil. Is it the vile Umberlee herself? A really passive-aggressive Kraken just sitting on an underwater couch, awaiting its next meal and treating the staff like they work for Postmates? Nobody in the tavern can say. All they know is that they must sate its hunger or something bad will happen. You don’t wanna know what happened to the bus boy. Okay; he had a nightmare about pitch-black barracuda-like demons eating him from the inside out, and he peed himself and jumped in The Pit. Busboys have it rough.

The Staff

Hestima is the tiefling bartender. Of late she has barely resisted the urge to throw herself in the pit, the only thing stopping her being a really hot sailor named Cleave who has been coming by lately. She will poison the drink of whoever looks most likely to have a pre-existing problem with ale-control, or better yet some sleepy merchant who looks in need of a room for rent. Hestima has learned through trial and error that The Pit (that’s the proper name they call it) prefers a conscious but paralyzed victim, and uses a chemical agent called gerkalilly. If anyone in a group of adventurers looks piqued or exhausted they’re on her list the moment they walk in. She’s not the only one planning to drug the patrons, but she’s the alpha sacrificer. A DC 18 Constitution saving throw must be made if you are served her marked drink. 

Smilin’ Janky is the permanent tavern bard, a halfling who sings long, slow, Decembrists-esque sea songs. If you like to roleplay bard songs as a Dungeon Master, feel free to borrow their lyrics and make them weirder as you go. Once players have had a drink, he will play a song whose third verse invokes a modified version of Sleep that the evil sea presence taught him, that looks like sleep but functions more like paralysis in that the character slumps over but is aware of its surroundings. Smilin’ Janky can cast up to third level, but adjust to your player’s level to be fair. He’s an experienced bard who used to adventure but got sucked into this little mini-cult and is too ashamed of himself to keep up his fighting skills beyond his signature song. 

Like everyone else here, though, ol’ Smilin’ Janky has commoner stats and will run out of the tavern shrieking if confronted. This is because everyone on staff is a coward at heart, and running away shrieking both lets one character look like the sole problem and is funny to describe.  

The server, Bonkiss, usually helps drunks to beds upstairs or the kitchen where he claims there’s “an extra room for those who can’t make it upstairs.” But it’s the storage room with the trap door. He will also help Hestima poison a drink with gerkalilly, help get patrons to sit near Smilin’ Janky while he performs, and will wink at the doorman if extra assistance is needed. Though the most cowardly, he is also the most wealthy as he has been justifying his fate by saving up money he's pilfered from the bar safe and his fellow employees. There's 57 gp hidden in a knot in the kitchen wall, and the other staff would be furious to find out about it. He tells himself he will use it to hire priests to banish The Pit, but really he's just saving it to get a priest to fix his personal curse. And maybe reward himself with gross treasures. Oh Bonkiss, you're a real creep. I hope a reader kills you.

The doorman, Digryph, is a sour dwarf who doesn’t talk much, and mostly keeps the flow of patrons manageable for the regular sacrifices and their secretive nature. He did learn one spell from the dark forces below, Darkness, and will only cast it if he needs to make his own escape. Really, Digryph? I hope a reader chucks you in The Pit when they find out how many people you've done that to. Which is eleven.

Cleave is a hot, briny chunk of dwarf. Still sailing from time to time, he has been staying ashore for a while to appease his new girlfriend Hestima and her whole secret murder hobby thing. He has great, veiny arms that are good at holding you, but mostly Hestima. He will enter the bar once the players have been there for a bit, ready to deploy a trained wasp into the room that will hunt for a player to paralyze. This exotic green wasp has the sting of a giant wasp but is tiny, has 2 hit points, and can only be detected by a creature checking their surroundings carefully and noticing it on the prowl, or looking at Cleave when he attempts to stealthily open the wasp’s jar. Cleave is really good at doing it stealthily though. I mean look at those arms. Yowza.

Recently Cleave discovered that Hestima inherited the bar from the old bartender, and has been grandfathered into this life of indecency. He’s the most suspicious, and can be convinced to betray the bar and the curse. A strong Charisma (Persuasion) check can get him to break down into tears, sobbing and blubbering about how hot and cool Hestima is. He'll ask you to spare her if it's not too late. Everyone else is too messed up from their weird wet nightmares to betray everyone else, but they'll do anything to lull a party into their own wet nightmares.

And if Cleave helps you he is definitely gonna go nutzoid later. Sorry Cleave. Love is hard.

There’s really no way to “win” this bar. The idea is to creep players the hell out. Affect the most Tim Burton-y voices you can summon, ask your Alexa to play some thunderstorm sounds for a noisy moody night outside The Fractured Porthole, and attempt to create a sense of claustrophobia. And as always, I’m hoping you can wedge this into an existing game, so let me know if you found a fun way to customize it and freak out your pals.

  Dan Telfer is the Dungeons Humorist aka Comedy Archmage for D&D Beyond (a fun way they are letting him say "writer"), dungeon master for the Nerd Poker podcast, a stand-up comedian, a TV writer who also helped win some Emmys over at Comedy Central, and a former editor of MAD Magazine and The Onion. He can be found riding his bike around Los Angeles from gig to gig to gaming store, though the best way to find out what he's up to is to follow him on Twitter via @dantelfer.