A Bestiary of Boss Monsters from D&D Beyond's Crooked Moon

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Transcribed content from our recent YouTube video: https://www.youtube.com/watch?v=m-qBdvV9S5k

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From a flaming, headless horseman riding vengeance across cursed roads… to a ghost train that ferries souls between life and death—today we’re diving into the legendary monsters of the Crooked Moon, from D&D Beyond. These aren’t your average dungeon crawlers. These are actually campaign-defining nightmares, more akin to a bestiary of “boss monsters” that you can throw at your gaming group in this Halloween-style setting.

So, let’s talk about my favorite four that will haunt your players forever.

Welcome back to Eternity TTRPG, your lantern in the dark woods of Dungeons & Dragons adventures. Today, we’re peering into the shadows for another awesome dive into one of my favorite D&D settings of all time – Crooked Moon.

Let’s dive right in.

We’re starting strong with the Galloping Headsman—a headless executioner based, of course, on the “headless horseman” from “the Legend of Sleepy Hollow.” The twist here is that the horseman is a centaur. Still missing his head, which is now filled with gouts of fire. But in my opinion, no Halloween, or Halloween-inspired campaign, is complete without a visit from the headless horseman.

In one hand, this legendary monster wields a massive two-headed axe that can literally decapitate a player if it crits. And in the other it holds a burning pumpkin skull, shifting with agonized faces.

This monster is cinematic. Imagine a chase sequence where the Headsman’s lair warps roads themselves—stretching paths, halving travel speeds, and giving the sense to players that they can never quite escape.

His weakness? The original skull he lost. If your players find and wield it, he suddenly becomes vulnerable. Until then… run.

I love boss fights where there’s a secret that players need to uncover, to make the battle well – winnable. Until that secret is uncovered, the “boss” feels truly like something of legends and nightmares.

Number two is another top pick that I think Crooked Moon absolutely nailed: the Ghostlight Locomotive. This one is just so different from anything you typically see in D&D, or almost any roleplay game. It’s a phantom train barreling between life and death, burning souls as fuel.

Most of the time, the Ghostlight Locomotive runs its eternal route, burning souls like coal, but carrying them off to the afterlife. But that balance is fragile. When its soul-fuel becomes corrupted—whether by dark magic, a curse, or too many wicked spirits—something inside the engine snaps. Suddenly it’s no longer mindless. Instead, the train becomes aware of the countless souls it has consumed, and with that awareness comes rage. That’s when the Locomotive transforms into a nightmare on rails, lashing out at the living and dragging anything in its path down into the mist.

And speaking of, the ghostly, mile-wide shroud of mist that surrounds the train prevents players from fully healing with rest, and even magic feels weaker—potions and cure spells only work at half strength.

Consider the power of the mist itself, this legendary monster is actually part dungeon, part boss, and even part existential crisis.

At number three, we move from machines to nature gone wrong—meet the Beast of Blight. Once, this beast was Farryn of the Greenwood, a druid who turned to forbidden magic to bring back her dead lover. And that, as you might expect is where things went wrong. Instead of restoring life, her magic twisted inward. Nature didn’t heal her grief—it reflected it, warping her body with rot, fungus, and decay. In trying to preserve love, she became the embodiment of loss: a beast that spreads corruption with every step.

Now, the Beast’s lair is a cavern at the heart of a rotting forest, where decay seeps even from stones. In that place, the natural world turns against you—forests wither, food spoils, and even spells that create water only produce half their normal amount.

In this cavern, the Beast can teleport through rot, spew necrotic spores, and even she can even impale grappled creatures on her exposed ribs, holding them restrained while dealing piercing damage.

But buried inside her, a flicker of Farryn’s memory or emotion that survived the corruption, remains. Show the Beast the likeness of her lost love, and for a moment, the rot burns away and Farryn comes back through. When this happens, she takes immediate psychic damage, and she also has Disadvantage on all d20 tests until the start of her next turn – making this fight much, much easier.

Lastly, we move to the Dusk Mother. Her keening wails carry through settlements, where she searches endlessly for her lost children. Some say they died from her wrath, others say it was from her negligence.

But in truth, it doesn’t matter how [her children died]—because in her own mind, she carries all the guilt. That shame, that unbearable grief, twisted her into something more than a ghost. It made her into the Dusk Mother.

Directly from Crooked Moon: “Now she cries in shame for that loss as she searches for her children, or for souls to claim and fashion into dolls in a futile attempt to fill the void in her doomed soul.”

The Dusk Mother carries giant shears and a great tolling bell, as she wanders across the countryside. Her presence warps reality—villagers absentmindedly start humming funeral songs, while adventurers become unable to rest.

Once again, the players may have some advantage though if they ever have to face her, for if she ever sees her children’s trinkets or spirits, she collapses, overcome with guilt.

This is the kind of boss fight that is emotionally heavy. In this case, your players aren’t just fighting a legendary monster. Instead, they’re facing an avatar of grief, itself.

So that’s four of the most terrifying legendary monsters from The Crooked Moon. The Galloping Headsman, the Ghostlight Locomotive, the Beast of Blight, and the Dusk Mother. Each one is packed with lore that can fuel more than a few game sessions, and interesting mechanical twists for climactic encounters.

But now I want to hear from you—if you had to unleash just one of these horrors in your campaign, which would it be? Would you make your players ride the Ghostlight Express, or see if anyone dares face the Beast of Blight head-on?”

Drop your pick in the comments, and don’t forget to like and subscribe for more D&D news and monster spotlights. Until next time—keep your head on straight… unlike the Headsman.

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10 Amazing D&D Quest Ideas for Your Next Game Session

By Jacob Tegtman • September 16, 2025

Transcribed content from our recent YouTube video: https://www.youtube.com/watch?v=3bMjDsFmYAc&ab_channel=EternityTTRPG Transcription Need some quick D&D quest ideas to throw at your players? Whether they’ve derailed your main storyline or you just need some fast inspiration, I’ve got 20 quests ready from my own 25+ years of D&D campaigns and one-shots that you can drop for your party at your next gaming night. From cursed artifacts to insane boss fights, these ideas will keep your party rolling dice all night long. Welcome back to Eternity TTRPG—your go-to source for all things Dungeons & Dragons. Today we’re counting down 20 quest and side quest ideas you can use instantly in your next game. Let’s dive in.” 10. Lava Core On the surface, this is a simple delivery quest—escort a wagon of supplies to a nearby town. But once the party leaves, the entire town erupts in flames. The merchant they worked for tricked them into delivering a magical explosive called the Lava Core to wipe out a secret organization. Now the players are left with guilt, betrayal, and a tough decision—do they hunt down the merchant, or try to redeem themselves? 9. The Jester’s Court Deep in the frozen tundra, a half-insane demi-god known as the Jester builds a kingdom of monsters. Think undead, beasts, demons—all following his twisted command. His influence spreads like wildfire, and the only way to stop him is to march into his icy castle and confront him directly. Of course, everyone knows that’s basically suicide. Which makes it the perfect quest for high-level heroes. 8. Three Sisters Here’s a boss fight with a puzzle built in: three enemies, known as the Sisters, must be killed in the correct order. If not, the survivors resurrect the fallen one on their next turn. The party needs to uncover hints about the order—maybe from a prophecy, maybe from symbols on their armor—before the fight turns into an endless nightmare. It’s a perfect way to mix combat and problem-solving. 7. Ruins of the Tree of Life This dungeon takes place inside the mile-high corpse of the Tree of Life. Its rotting branches are filled with undead and pestilence, and at the top lies a black crystal prison holding Ranroth the Betrayer. Only, that prison is cracked and about to shatter. Do the players attempt to repair the seal, or prepare for the return of one of the realm’s greatest enemies? 6. Fang of Lanias This is the tooth of a fallen golden dragon. Whoever holds it can summon the ghost of Lanias—but instead of a wise guardian, the spirit attacks anyone who enters his ruined spire. If the party doesn’t banish him properly, Lanias resurrects at midnight every night, forcing an endless cycle of battles. Do your players destroy the fang, or find a way to put this restless dragon to peace? 5. Ultimate Vampire Vampires are scary enough, but this one is pure nightmare fuel. At the start of combat, he drains one character level from each party member, and he rips away their strongest magic item, adding its powers to himself. Imagine watching your sword of legend floating in his hands as he uses it against you. It’s a brutal reminder that sometimes, the deadliest monsters aren’t just strong—they’re thieves of everything you hold dear. 4. Crypt of the Plaguebringers Plagues are spreading across the realm, and clerics can’t heal them. Why? Because it’s no ordinary sickness—it’s fueled by a cult using trapped spirits from a hidden crypt. If the party doesn’t stop them within thirty days, the plague will cover the land. To make it worse, the spirits themselves whisper to the heroes in their dreams, offering dark bargains in exchange for helping, rather than hindering them. 3. Future Disaster Not every quest the heroes undertake has a happy ending. A humble family asks the party to mentor their gifted child in magic. Over time, the child becomes a prodigy—but also grows up watching the adventurers use their power to shape the world. Eventually, that child returns as the party’s greatest enemy, convinced they can rule better than their mentors. It’s a heartbreaking story of legacy and unintended consequences. 2. Reverse This boss breaks one of D&D’s core rules: damage heals them, and healing hurts them. Imagine the party unleashing fireballs, only to see the monster’s wounds close tighter each time. The only way to kill it is through healing spells or potions, which means your party’s cleric suddenly becomes the MVP damage dealer. It’s one of those fights that makes your players go, ‘Wait… what?!’ Or, imagine if they have no dedicated healer in the party and now must win using an entire town’s literal stockpile of healing potions. 1. Unicorn Meat A vendor in the town square loudly declares he’s selling—yes, you heard it right—fresh unicorn meat. It shimmers rainbow hues, smells like summer fields, and nobles are lining up to buy it by the pound. The butcher swears it’s ethical—‘No problem if you *find* them dead!’ he says. But his business is booming so fast he needs help finding more. That’s where the party comes in: track down dead unicorns, bring back the meat, and he’ll cut them in on the profits. Of course, unicorns don’t usually drop dead on their own. But if something is out there killing them, the heroes will have to decide—do they protect these sacred creatures, or cash in on the newest, most lucrative and controversial trade in the realm? And that’s ten amazing D&D quest ideas—from tragic mentor-protégé betrayals to bizarre unicorn steaks. Which one would your players love—or absolutely hate—the most? Drop your pick in the comments, and don’t forget to like and subscribe for more D&D content every week. Until next time, may your dice roll high, and your weekly adventures always turn into legendary stories.

Journey Adventure Quest - DnD Board Game to Inspire Campaigns

By Jacob Tegtman • September 12, 2025

Transcribed content from our recent YouTube video: https://www.youtube.com/watch?v=3N4UZQypmuo&ab_channel=EternityTTRPG Transcription What if you combined the card drafting of a deckbuilder, the equipment-sets of a loot quest, and the hidden personal goals of a role-playing adventure—wrapped up in a compact competitive board game? That’s “Journey Adventure Quest” – or JAQ, for short. This is a game my wife and I picked up at GenCon, and I’ve really enjoyed. In our first playthrough at the convention, it felt like there was a lot to wrap my head around. But we just played the game again for the first time since GenCon, and it made perfect sense – after a thorough read through the rulebook. In today’s video, I’ll break down what I like about Journey Adventure Quest, whether you as a D&D fan may like it, and some basic info on how the game is played in case you want to pick it up. JAQ is a competitive (or semi-cooperative / even solo) tabletop/ card game about fantasy heroes growing in power, fighting monsters, building gear and spell combinations, and completing quests. I’ll get into the game in more detail shortly, but for the bulk of this video I actually want to just share what I like best about the game – which are some very specific things. Whenever you get a new piece of equipment for your hero, you can “stack” it on gear of the same type. The way that you do this is to actually leave the card top and left side uncovered, which actually empowers your equipment. This style of gameplay reminds me a lot of early gaming experiences I had with D&D and other RPGs where you finally get your first +1 Longsword. Sort of, before the days of World of Warcraft style play, where you’re just getting the newer, badder glowing sword that adds 1,000 more DPS than you had before. I like that in Journey Adventure Quest, every upgrade adds to the stats of the equipment you had before, and also gives you a unique name. This style of equipment upgrade works for all the gear you’d normally have in a D&D campaign, or other RPG – chest armor, helmet, gloves, belt, weapon, and even your spells! And there’s no limit to how much you can “stack” on one equipment piece. We’ve had some games where one of us had like 8 weapons on top of each other, and was just the most insane gear you could imagine. This stacking and naming effect makes the equipment begin to feel legendary, and incredibly powerful, even though you’ve had the basis for it from the very beginning of the game. This “feel” of equipment upgrading actually isn’t all that important to the gameplay at all, to be honest haha. You’d probably think from me going on about it that it is, but to me the feel is valuable enough for why I like it so much, and it’s a great idea for even your next D&D campaign – emulating something like this. Similar to stacking equipment, you actually do the same thing with monsters. Basically, to defeat it you need both strength, and knowledge for how to bring it down. Your goal (in my cases) is to gather enough strength and knowledge through your gear to overcome the monster. But, when the monster levels up, you do the same thing with stacking the cards so they still show the top and left-hand side. The final thing I want to point out that I really like about the game is that your character actually can’t “die.” Instead of taking “damage” that get removed from your total HP – like you’d see in most games or RPGs – you instead take 1 “blood” marker for each damage you’ve taken. At the end of the game, all of your “blood” markers reduce your overall score, so you can still basically “lose” the game (kind of) from taking too much damage. But it’s really fun – and pretty funny also – that the game has these awesome equipment and monster mechanics, but you actually have no risk of character death. For a low-key, fantasy-adventure, fun/ party kind of game, I really like the low stakes nature of the game. In one game, I think my wife had like 18-blood on her character – which is a ton, by the way. She basically had 0 armor all game, didn’t even try to reduce the damage she was taking – and ended up still winning because she completed all of her character’s quests, in other ways. Super fun. So, here’s roughly how the game is played, overall. Heroes get an initial hand of 7 cards to draft equipment, spells, or other items. Equipment has a cost to it (either in coins, or blood), and you basically just choose what you want for your character. After every two rounds of drafting cards for your hero to power them up, you face monsters. Everyone who can defeat the monster – by overcoming their knowledge and HP – gets rewards, like you can see here. And then, each monster also comes with specific loot drops, which only one player may acquire, based on specific requirements for each loot card. After a monster is defeated, players returning to drafting more equipment and cards to boost their heroes. There are three total “rounds” of fighting monsters. While all of this is happening, there are personal secret adventures : each hero has some hidden goals that often require high-level spells, powerful equipment of a certain type, or certain “colors” that go into their equipment – these are known as guilds. I think of them basically just as being elemental types. Finally, there are quests , which are basically adventures that everyone’s on, to either compete for end-game prizing, or to at least hit certain thresholds where bonuses are given. At game end, the hero with the most points – which you get from a combination of equipment / monster fights / secret adventure completions/ quest/comparisons and) – actually wins the game. To summarize it, the game utilizes a very fun drafting mechanic for gear where you’re building combos, guild-sets, spells and equipment that synergize. You have progressive escalation of your very cool equipment, and monsters you battle. Players have hidden goals that add a roleplay-like flavor, and gives each player a sort of personal story they’re pursuing. And then you have multiple paths to victory: through direct confrontation/quests, through your hero’s power, through completing your secret adventures, and more. All of this a adds replayability, strategic variation, and a sense that you’re sort of roleplaying a character through this board, card game. M any D&D fans enjoy storytelling, character growth, equipment/spells, quests, sometimes hidden motivations, and fighting monster. I would say that journey adventure quest delivers on all of these. What JAQ might not deliver (for D&D fans) would be: Narrative depth, Roleplay flexibility, and stuff like Dungeon exploration and world building. So, it isn’t a replacement, obviously, but if you like D&D and want a light version of a D&D-feeling game, I think you’d have a lot of fun playing JAQ for an hour or two on some afternoon you have free. So there you have Journey Adventure Quest — a game that blends drafting, hero building, secret goals, and monster combat into something strategic, replayable – and most importantly, fun. For many D&D fans, especially those who love loot, spells, and character growth, this is worth a look. If you’ve played the game (or get a chance to), let me know your impressions. Thanks for watching—don’t forget to like, subscribe, and hit that bell so you see when we cover more hybrid adventure/ strategy games amidst our journey into D&D!

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Crooked Moon Sorcerers, Warlocks, and Wizards - Gothic Subclasses

By Jacob Tegtman • September 10, 2025

Transcribed content from our recent YouTube video: https://www.youtube.com/watch?v=1FWHvMzf_nI&ab_channel=EternityTTRPG Transcription We’ve reached the grand finale of our journey through Crooked Moon. If you thought alchemical barbarians and plague monks were wild—wait until you see sorcerers turning into pools of blood, warlocks who serve a cosmic jester, and wizards who poke holes in reality itself. This is where things get truly unhinged. Welcome back to Eternity TTRPG—your go-to source for all things D&D. This is Part 3 of our dive into the Crooked Moon subclasses, and the final five might just be the most dramatic of them all. We’ve got blood magic, chaotic laughter, witchcraft bargains, and two wizard paths that pull on the strings of reality. 1. Sorcerer: Crimson Sorcery Crimson Sorcerers channel raw lifeblood as their source of magic. Their powers revolve around something called the Blood Well—a reserve of vital energy they can spend to boost damage, enhance healing, or fuel their abilities. They can even dissolve into a literal pool of blood, slipping through cracks and resisting damage like some vampiric horror. As they grow stronger, they siphon life from their own body to supercharge spells, and eventually unleash Sanguine Feast—tendrils of blood draining everyone around them while restoring their own vitality. It’s absolute blood magic—a perfect subclass for anyone who wants their sorcerer to feel dangerous and unsettling. 2. Warlock: Great Fool Patron Not all horror is blood and gloom—sometimes it’s laughter. The Great Fool is a cosmic jester patron, and its warlocks wield humor as a weapon. They lash out with Vicious Mockery as a reaction, slap curses on enemies that leave them blinded by flowers, clumsy with clown shoes, or honking uncontrollably every time they move. At higher levels, their banter deals psychic damage, and eventually they can Send in the Clowns—summoning ghostly jesters that strike fear and knock enemies prone. It’s creepy circus energy meets eldritch pact, perfect for players who like their dark fantasy with a side of twisted comedy. Real quick to interrupt, we now have free downloadable D&D cards at the Eternity TTRPG website that you can use at your table. Everything from combat actions to status effects – no more flipping through your book to see exactly what being “Petrified” does to your character. You can just take our graphics, print them out at home, and slap them on your table for fun and easy reference. Grab yours today using the link, below! Now, back to the video. 3. Warlock: Horned King Patron The Horned King reminds me, of course, of the Black Cauldron! ...So I already have nostalgia for it. This class is the darker side of warlock pacts—witchcraft, maledictions, and the like. These warlocks curse enemies with agony, rot, or madness, and later channel the Horned King’s majesty by sprouting antlers and radiating an aura that charms, terrifies, or weakens foes. At their peak, they can even form a coven—bonding allies to share curses, teleport across the battlefield to each other’s sides, and spread extra necrotic damage. Thematically, this one screams ‘folk horror witchcraft’—rituals in the woods, blood pacts, and the slow transformation into something more than human. 4. Wizard: Occultist Occultists are the wizards who say, ‘knowledge at any cost.’ They reach beyond the stars, tearing open the veil of reality for forbidden secrets. Their unique mechanic is the Intrusion Die—every time they push their magic, reality might fight back, causing strange intrusions from alien realms. In exchange, they get immense power: removing concentration requirements, teleporting through scrying spells, and even flying or resisting madness. It’s the perfect subclass for players who want their wizard to feel like they’re constantly balancing brilliance with cosmic horror. 5. Wizard: Philosopher Where the Occultist seeks forbidden knowledge, the Philosopher seeks ultimate truth. These wizards distill existence into Quintessence—a crystalline powder created from dissolving creatures or objects with their magic. That quintessence can then be spent to boost spell levels, craft magic items, or even alter the damage type of spells. Eventually, they craft a philosopher’s stone, granting them immortality, the ability to supercharge spells, and even cheat death itself. It’s the alchemical dream realized—equal parts academic and arcane. And that’s it—the full lineup of Crooked Moon’s subclasses. Fifteen in total, ranging from blood-soaked sorcerers to those we covered in previous videos, like the plague monk, and alchemical barbarian. This supplement doesn’t just remix the classic D&D classes—it drenches them in gothic horror, folk myth, and cosmic strangeness. If you’ve stuck with us through all three parts, thank you. Now I want to know—which of the fifteen subclasses across this series is your absolute favorite? Drop it in the comments, and let’s see which one takes the crown. And if you enjoyed this series, be sure to like, subscribe, and share it with your table—because who knows, maybe your next campaign could use a paladin bent on the inquisition, or a spectral ranger.

A Bestiary of Boss Monsters from D&D Beyond's Crooked Moon

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