There are few Halloween spirits quite as iconic as Washington Irving’s headless horseman. Even within the pages of the original Legend of Sleepy Hollow he was equal parts spirit and scary story.
“The dominant spirit, however, that haunts this enchanted region and seems to be commander-in-chief of all the powers of the air is the apparition of a figure on horseback without a head. It is said by some to be the ghost of a Hessian trooper, whose head had been carried away by a cannon ball, in some nameless battle during the Revolutionary War, and who is ever and anon seen by the country folk, hurrying along in the gloom of night, as if on the wings of the wind.”
The Ethereal who wears this mask tends towards the dark and terrible rider, the part of the story that is best remembered. However, if you read to the end there is a strong hint that the dark rider was none other than Brom Bones, a talented storyteller and town bravo who took on the role as a way to scare his rival Inchabod straight out of Sleepy Hollow.
The Headless Horseman is no longer quite so obvious, but he still likes sneaking into the mortal world, building up a Role as a typical and perhaps even desirable human, and using the social cache this affords him to plant the seeds of new nightmares he can make use of during his hunts.
The Galloping Hessian of the Hollow
Etherial Spirit of Fear and the Hunt [7/28 ]
Corporeal Forces: 3 [Strength 5, Dexterity 3]
Ethereal Forces: 2 [Intelligence 5, Precision 7]
Celestial Forces: 2 [Will 5, Perception 3]
Inherent Dread: Being Bested/2
Strong Affinities: Emotion(Fear) 
Moderate Affinities: Obscurement , Puissance (Shot) 
Slight Affinities: Animals (Horses) , Fire , Speed , Terrain (Swamp) 
Role: 2/4 (Pick something that fits your campaign) , Charisma +1 
Skills: Animal Handling/1, Artistry (Storytelling)/3, Dodge/2, Dreaming/2, Driving (Motorcycle)/2, Fighting/3, Move Silently/2, Riding/4, Seduction/1, Throwing/3
Special Attunement: Ghost Story
While telling a scary story, the Headless Horseman may spend 1 essence to implant the threads of his own being into the minds of the listeners. This has two main effects.
- The Horseman can use his Storytelling skill to dream-shape the dreams of his listeners before they even fall asleep.
- The Horseman can find and enter the dreamscapes of his listeners for the next night as if he had Dreamwalking. The effect does not last more than a single night and only extends to those who heard the horseman’s story.
The Horseman’s Shot
The Headless Horseman is undoubtedly a cunning pitcher, but his puissance tends to kick in when throwing something heavier or more ungainly than a baseball. Here are a few things he might be found throwing:
While in the Marches the Headless Horseman will create a flaming gourd (most often a jack-o-lantern) with his puissance ability. It will shatter on contact, creating a fiery splash effect. I would treat this as 1 damage effect to anyone within 2 yards of the target, dodging allowed. It also adds flame to the dreamscape, thereby increasing the Horseman’s Dreaming rolls.
Incorporating the Horseman
While it can always be fun to have the Horseman ride free among the humans, he is no real match for any angel or demon while in the open.
It is far more likely that he will have integrated himself into a community of humans. There he will spend his days proving his superiority and his nights terrorizing anyone fool enough to contest that superiority.
This will eventually cause enough of a disturbance that an Angel of Dreams or Demon of Nightmares will be sent to check out the community. However, they will need to be careful not to tip their hand. If the Horseman learns that a Celestial is sniffing around for him, he will leave town rather than let himself get caught and bested.
However, should a confrontation become inevitable, it is worth remembering that the Horseman will be on home territory and he will have almost certainly sculpted the dreamscapes of the local population to favor one or more of his affinities.
Should a Celestial manage to best the Horseman, they can potentially purchase him as a Class 8 Servant. However, the spirit will only willingly work with someone who allows him to keep hunting. While it might be possible for an Angel of Fire, The Sword, or Judgement to come to terms with him, it’s far more likely that the Horseman would join forces with a Demon.