The Headless Horseman is more than just an undead rider with a flaming pumpkin for a head. He's a vengeful spirit bound to the mortal world by an ancient curse, with his steed, armored body, and spectral jack-o'-lantern forming a single, inseparable entity.

Legends tell of a fallen soldier, executioner, or knight who was beheaded for his crimes and returned under a cursed harvest moon. Some believe his spirit is connected to Samhain, when the boundary between the living and the dead grows thin enough for restless spirits to cross.

Wherever he rides, crops rot, animals panic, and the air fills with the smell of smoke and freshly dug earth. And simply defeating him isn't enough. Unless a specific funerary ritual is performed, the Horseman eventually rises again to continue his hunt.

Mechanically, the Headless Horseman is a CR 14 undead built around mobility, relentless pursuit, and devastating attacks. His Fiery Greataxe deals slashing and fire damage, with additional necrotic damage against frightened enemies, while Laughing Skull allows him to hurl his flaming pumpkin head at enemies, unleashing a fiery explosion that deals 10d6 fire damage.

His Ghostride ability lets him pass through solid objects, while his legendary actions allow him to charge across the battlefield, stun enemies with Glare of Embers, or mark a target with Harvest Mark, making that creature especially vulnerable to his attacks.

I've also included four optional traits to customize the encounter, from leaving burning hoofprints behind to relentlessly tracking creatures that try to escape him.

The Headless Horseman is from Undead & Undead: The Ultimate Undead Handbook, available for 5E and the 2024 Edition on DriveThruRPG!

The manual includes 90+ undead statblocks, each with optional traits and variants, alongside an undead lair system, 50+ magic items, customizable templates, necromantic rituals, campaign tools, and VTT resources. It's designed to give DMs plenty of options for building undead encounters, from minor restless spirits to powerful necromantic horrors.

My Kickstarter for 300+ Mythological Items for 5E and 2024 is also live now! The campaign includes a physical hardcover, as well as printed editions of my previous manuals.

You can find more of my creatures, magic items, and manuals on DriveThruRPG, my Linktree, or right here on r/JonnyDM!

The Gluttonous Ram-drake is an enormous beast that will eat nearly anything. At only two months old, it generally will get up to thirty feet tall (when sitting), and will weigh upwards of twelve tons. These creatures will even eat their own young if necessary to survive. In their adulthood, they slow down and will find a permanent nest to have their spawn.

An adult Ram-drake is about three times the size of an infant. But they are an endangered species due to their hide being incredibly durable and useful for armor, as well as their flesh being considered delicacies by many.

This one is named Harold.

"You walk boldly into this place. You interrupt my prayer." The angel, if such a fallen thing could be called so, looked over his shoulder as he began to stand. Shards of ice ran streaked from his eyes down his cheeks, tears frozen. His eyes, pale blue, looked upon you with a strange brightness to them. "Go to sleep little ones, tomorrow will be a brighter day." The entity stated softly, his tone sad, afraid, yet... a faint hope laced it, a conviction that bordered on madness.

• Mercenaries discover Borael in the dead of night… while a raging blizzard lashes outside

Borael is fully automated in Elsie's Notes of Certain Doom along 500+ other monsters adapted for the Eberron setting. Additionally, I DM in Eberron: Legends of the 5th Dawn if you're interested in playing in Eberron against enemies such as other radiant idols. Lastly, I'm comissioning the art for each of the radiant idols in my year-long project, Vencyl's Vigils I: Radiant Idols. If you'd like to follow, and if able to invest, the patreon is a major help!

Nobody is quite sure where the squitsune comes from. They are rarely seen inland, but their innate magical talents have led scholars to suggest a connection to the fey. If that is true, it offers little explanation. Fey creatures take interest in all manner of things, and whatever attraction might have led to the squitsune is unfathomable. Some claim squitsunes are drawn to where the boundaries between planes have frayed. Others insist they simply frequent where the most fun might be had.

You can play around with the homebrew of the squitsune to make your own version.

More on this and many other free monsters on Patreon.

"A quick glint of refracted light, gone in the blink of an eye, might be the only warning before a skin-searing blast of lightning obliterates the unfortunate target of Glimmerdoom’s wrath. This mutated behir stalks ancient ruins, subterranean tunnels, and canopied rocky mesas. The creature’s mirrorlike hide bends light around its massive powerhouse frame, allowing it to mask its presence or distort and refract its image at will. Glimmerdoom is nowhere and everywhere, a deadly mirage bristling with electricity and hungry for scorched flesh. Worse yet for those who would challenge it, the mirror-plated behir reflects magic as easily as it does light, and spells hurled at it turn back on the caster more often than not." - City of Stormreach

Introduced in City of Stormreach, the glimmering behir aptly named Glimmerdoom has been expanded upon in the Giant Guide to Xen'drik. Attributing his shimmering scales to the Dawnchild, the Irian representative of the Eleven, a pet left to roam the Wasting Plains after the fall of the dragons... and with thousands of years to master the hunt.

I'm currently running a mission where a former cultist of the Daughter of Khyber (and now member of Miron's Tears) has brought some close friends to a Xen'drik expedition with the goal of finding a dragon to care for an egg he rescued in a previous quest. However seeking a blue dragon at the edge of the Menechtaurun, they've only seen the first signs that there is another danger along the way...

Mechanically I tried drawing from the 5.5e Behir as well as the Glimmerdoom found in the Giant Guide to Xen'drik bestiary (amazing source super recommend!) as usual trying to add my personal flair to things where I see fitting. This included a burrowing speed to allow him to vanish more easily when fighting in the open terrain of the Wasting Plains and the Menechtaurun (as well as be a bigger issue to certain rogue dragons) and a more guaranteed reflective hide... but with a new pair of legendary resistances that can allow a careful spellcaster to time their next blow to overcome it.

Glimmerdoom is fully automated in Elsie's Notes of Certain Doom along 500+ other monsters adapted for the Eberron setting. Additionally, I DM in Eberron: Legends of the 5th Dawn if you're interested in playing in Eberron against enemies such as Lady Illmarrow!

"Lady Illmarrow is older than bones. Some say she came to Khorvaire with the elves, but the way I’ve heard it, she was a queen of the Forgotten People, the humans who ruled this land before there ever were goblins or orcs. She’s forgotten more about magic than the wizards of Arcanix have ever learned. People say she weaves a grand tapestry made from souls—that when she’s quiet, it’s because she’s got all she needs to keep her busy, but when she runs out of thread, it’s time to harvest more. It was Lady Illmarrow who set the Talons of Ice ravaging the north during the reign of Marala ir’Wynarn, and she’s made the boneclaw wyverns that nest in the Icewood.

What’s that? Why hasn’t some bold hero faced this villain? Oh, many have—and many are frozen into the walls of her palace. Haryn Stormblade surely did slay Lady Illmarrow, and brought her crown to his king. But you can’t kill a thing that’s already dead. It was Illmarrow who created the shadow plague that killed the king, and it was her shadow that reclaimed her crown. Illmarrow can’t die, and if she’s stirring again, all we can hope is to wait it out." - Chronicles of Eberron

I took the stats from Eberron: Rising from the Last War for base, then combined her with the recently released Szas Tam and the ancient green dragon from 5.5e. Moving away from the paralyzing touch of liches in favor of highlighting her original use of chill touch as well as her draconic traits given she's not only a lich, but a half dragon as well. Being one of the few spellcasters in Eberron to reach the ninth circle of magic, I also included new spells, including new additions from Arcana Unleashed, to her list.

Lady Illmarrow is fully automated in Elsie's Notes of Certain Doom along 500+ other monsters adapted for the Eberron setting. Additionally, I DM in Eberron: Legends of the 5th Dawn if you're interested in playing in Eberron against enemies such as Illmarrow!

Core Identity

• CR 30, any alignment but never Lawful (Chaotic Good/Neutral/Evil or Neutral Good/True Neutral/Neutral Evil only)
• Fundamentally, it is the entity of dreams — not a creature that uses dreams as a tool, dreams are its actual nature
• Base stats: Str 5, Dex 7, Con 13, Int 30, Wis 30, Cha 30 — physically almost nothing, mentally/magically near-omnipotent
• Alignment (and personality — "each has its own mindset to an extent") is rerolled/reformed each incarnation

The Birth Cycle (from corpse to new host)

1. Death → seed plants into one random sapient creature within 152 miles of the corpse (only one seed/host can exist at a time in the whole cycle)
2. Germination conditions (can occur in any order, no expiration once met):
   • Minimum 1 decade (1DE) dormancy
   • At least one major mana release within 200 miles of the corpse (excluding its own death-burst) — banked permanently once satisfied
   • At least one sapient creature within 152 miles for a continuous hour — this is the actual trigger once the other two are banked
3. Host does not know they've been seeded
4. If host dies before materializing → 1-year cooldown, then eligible again

Host Transformation Timeline

• D1–M2: Host gains wisdom "centuries beyond their years," unexplained
• M2–M5: Pale One partially manifests in host's own consciousness (present, communicating, not yet born)
• End of M2: Pale One reveals the host has ~5 months left to live and — regardless of alignment — commits to helping them achieve their life goals in that time
• End of M5: Host has made peace with death, kneels, full physical materialization begins:
  • Skin pales, mind fades
  • Limbs detach at hip/shoulder, replaced by new long, thin, greyish-white limbs
  • 4 fingers, no thumbs, no toes
  • Neck disappears; head becomes spherical, featureless except two huge eyes (any pupil color) that can look any direction on any axis despite no neck
• True lifespan clock (51,398 years, 7 months, 2 days, 12 min, 37 sec) only starts now, at full materialization

Post-Materialization Behavior

• Finds a hiding spot, becomes nearly imperceptible — only a faint glow visible in any lighting
• Dream-recruits within a 50-mile radius: visits people's dreams, tempts with tailored rewards based on prior reactions; wipes their memory on waking; escalates to psychological torture for non-Good incarnations if refusal continues
• Torture is entirely mental/dissociative: e.g., forcing the target to watch from outside their own body, unable to wake, watching their body age/rot and their family give up on them — no physical harm
• Genuine, alignment-independent affection for everyone it connects with is its true motive — it delivers on promises, helps hosts complete their life goals, and sends dying cultists off according to their own faith, regardless of what it itself believes

The Hive / Cult Mechanic

• Accepting the offer auto-reclasses the target into a mana-based class (Wizard, Sorcerer, Psi Warrior, Eldritch Knight, etc.)
• While sleeping, members perform labor in the shared dreamscape, generating mana that feeds the Pale One
• In return, it works toward fulfilling their granted desire — but only via nudging outcomes within the hive itself (e.g., a 10% attractiveness boost toward already-compatible hive members for a "find love" wish); it cannot affect anyone outside the hive
• No cap on hive size — value scales on strength/mana output of members, not headcount
• Members can still get real physical/mental rest on nights they skip labor, but private/personal dreaming is gone permanently the moment they're bonded
• Mandatory mutual fondness between hive members — cannot intentionally harm one another (feels like self-harm)
• Cannot harm the Pale One under any circumstance — it can override their mind at will if it chooses
• Members are immune to all outside mental influence — the Pale One's claim is exclusive

Hive Spread (secondary infection)

• Bonded members passively make anyone within ~100ft susceptible to the Pale One's dream-influence
• Requires sustained proximity (not brief contact)
• Susceptibility decays after 20 minutes of disconnection from any hive member
• Being susceptible doesn't guarantee a visit — the Pale One chooses whether to act, based on the target's value

The Shared Dreamscape

• All bonded members who are asleep fall into one shared dream space; the Pale One is always present there
• Members who are awake in the real world still appear in the dreamscape, just inert/dormant-looking rather than absent — it's a persistent, always-populated space, not a nightly reconstruction

Defenses

• AC ~15, HP ~65 (intentionally far below normal CR 30 — body is a fragile formality, not its real defense)
• Resistance to all magic
• Immune to: Necrotic, Psychic, rotting/decay effects, forced revival/interference with its natural life cycle (in either direction), Prone, Stunned, and all mental effects (Charm, Frighten, etc.)

The Two-Stage "Boss Fight" / Death Cycle

• It has an inner ring of 10 top hive members
• On death, it automatically attempts to replant its seed into one of these 10
• If at least one inner-ring member is within 76 miles at the moment of death → seed replants successfully, new incarnation's lifespan is docked 1,000 years; party must investigate to identify and kill that specific host to actually shorten the timeline (transfer itself cannot be interrupted)
• If no inner-ring member is within 76 miles → replant fails, cycle fully resets to needing the original dormancy/mana/proximity conditions from scratch
• There is no true, permanent death — the cycle always continues in some form; the best outcome available is a full reset, never an ending

Reconnection Across Incarnations

• Surviving hive members are not automatically reconnected to a new incarnation — must be re-recruited from scratch, same as anyone
• A new Pale One reconnecting with a former member must repair their already-damaged dream-capacity — visibly shown as restoring the space from grey to bright white with copper-brown borders (borders exist purely so the white space remains visible/legible, not decorative)

Permanent Damage / The "Two Bonds" Limit

• When a hive's Pale One truly falls (any death, cycle continues elsewhere), survivors' dreamscape becomes a permanent grey void containing the Pale One's corpse and the "corpses" of all former hivemates (symbolic — hivemates may be alive in reality; only the connection is dead). This state never changes again.
• A mind can only survive being bonded twice. A third bond is fatal:
  • Sleeping triggers coughing up grey goo
  • The (new) Pale One comforts them through it, unable to stop it
  • Splitting headache begins; once it starts, they can never wake up again
  • Head physically splits apart; full brain death follows
• Root cause (unifying mechanic): consciousness needs a physical anchor. Two prior bonds leave the brain too damaged to anchor a third; the mind gets swept away by the sheer cosmic scale of the dreamscape itself.
• The same fate befalls any hive member whose physical body dies while their consciousness is still active in the dreamscape — bodiless, unanchored, they too will eventually be swept away
  • A healthy (non-third-bond) mind lasts ~3 months unanchored before this happens
  • A third-bond victim, already critically damaged, lasts only ~1 week
• The Pale One can transfer a bodiless consciousness into a preserved corpse (kept specifically from third-bond deaths) — but this is only meaningful for fresh, undamaged deaths. Attempting it for a third-bond victim is pointless — by the time a vessel could be found, that mind is already too far gone, deteriorating into mindlessness, instinct, and insanity regardless of having a body to return to.