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Epic Monsters: Headless Horseman (5E)

In our entry for Epic Monsters today we’re looking at a common motif in European folklore that didn’t really get its footing until The Legend of Sleepy Hollow. I’m talking of course about the Headless Horseman!

In our entry for Epic Monsters today we’re looking at a common motif in European folklore that didn’t really get its footing until The Legend of Sleepy Hollow. I’m talking of course about the Headless Horseman!


In the American tale it’s a Hessian soldier (German mercenary) that loses his head when a cannonball decapitates him and, buried without it, he rises to find it. Conversely the Dullahan in Ireland is an Unseelie fairy that knows precisely where its head is--tucked under one arm--and wields a spine-whip in one hand. In Scotland he’s got no head again but neither does the horse. In England it gets a little creeper with Gawain and the Green Knight; after being beheaded, the Green Knight picks up his own head and declares he’ll be back to challenge Gawain again in a year’s time. Germans like to give him a horn and sometimes fire-licking bloodhounds but the Indians have the coolest version: jhinjhārs, heroes that are too stubborn to die and instead fight to protect innocents from unjust or wrongful deaths.

Design Notes: Most people associate the Headless Horseman with the Ichabod Crane story but given how nebulous this character is across countries I’m taking the opportunity to make a monster with my favorite parts from each that’s ideal for GMs to use for striking a touch of terror in the hearts of players! Death’s Calling is however taken more or less from the excellent Pathfinder Roleplaying Game: Bestiary 2 statblock for the dullahan. For the CR statisticians out there, HH came in at 6.5 using the Blog of Holding system and 5.5 from the DMG so I settled on 6.

Headless Horseman
Medium undead, chaotic neutral

Armor Class
16 (natural)
Hit Points 68 (8d8+32)
Speed 30 ft.

18 (+4)​
16 (+3)​
19 (+4)​
14 (+2)​
15 (+2)​
17 (+3)​

Skills Animal Handling +5, Athletics +7, Intimidation +6, Perception +5, Survival +5
Damage Resistances acid, cold, fire, lightning, thunder; bludgeoning, piercing, and slashing from nonmagical attacks that aren't silvered
Damage Immunities necrotic, poison
Condition Immunities charmed, frightened, exhaustion, petrified, poisoned
Senses blindsight 30 ft., darkvision 120 ft., passive Perception 15
Languages the languages it knew in life
Challenge 6 (2,300 XP)

Incorporeal Movement. The Headless Horseman can move through other creatures and objects as if they were difficult terrain. He takes 5 (1d10) force damage if he ends his turn inside an object. The Headless Horseman can use his bonus action to share his Incorporeal Movement trait with a creature he is touching until the start of his next turn.

Innate Spellcasting. The Headless Horseman's innate spellcasting ability is Charisma (spell save DC 14). He can innately cast the following spells, requiring no material components:
At will: detect magic, phantom steed
3/day: gust of wind, misty step
1/day: blight

Magic Resistance. The Headless Horseman has advantage on saving throws against spells and other magical effects.

Regeneration. The Headless Horseman regains 5 hit points at the start of his turn. If the Headless Horseman takes radiant damage or damage from holy water, this trait doesn't function at the start of his next turn.


Multiattack. The Headless Horseman uses its Frightful Presence and attacks once, or he attacks twice: once with his chilling blade and once with his spinal whip.

Chilling Blade. Melee Weapon Attack: +8 to hit, reach 5 ft., one target. Hit: 9 (1d8+5) magical slashing damage plus 4 (1d8) cold damage.

Spinal Whip. Melee Weapon Attack: +8 to hit, reach 10 ft., one target. Hit: 8 (1d6+5) magical bludgeoning damage plus 4 (1d8) necrotic damage.

Death’s Calling. The Headless Horseman can use an action to place a death’s calling on a creature he can see within 60 feet. The target makes a DC 14 Charisma saving throw. On a failure, for 1 minute the target can’t use reactions and on its turn, it can use either an action or a bonus action, not both. A target can use its action to repeat the saving throw, ending this effect on itself with a success. In addition, until the target takes a long rest all weapon attacks against it score a critical hit on a roll of 19–20 and it automatically fails death saves.

Frightful Presence. Each creature of the Headless Horseman's choice that is within 100 feet of him and aware of him must succeed on a DC 14 Wisdom saving throw or become frightened for 1 minute. A creature can repeat the saving throw at the end of each of its turns, ending the effect on itself on a success. If a creature's saving throw is successful or the effect ends for it, the creature is immune to the Headless Horseman’s Frightful Presence for the next 24 hours.

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Mike Myler

Mike Myler

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