The Headless Horseman

Overview

The darklord of the Winding Road. He seeks his lost head (see: Headless Horseman's Head). The Headless Horseman is a legendary figure throughout the Core and beyond, with an endless number of possible local variant origin stories.

The Headless Horseman carries a wicked sickle that can cleave a person's head off with any clean blow. He is not inhibited by most spells that impede movement, and he is unaffected by turning. The Horseman's fearsome activities have not gone unnoticed, as he is a subject of fear spoken of in ghost stories in at least the domain of Borca.There, he is said to have been a victim of Lady Ivana Boritsi's dangerous whims, a bard that failed to provide her with amusement. Unusually, Ivana did not poison him, but instead ordered his decapitation, due to the crescent shape of the moon. Elsewhere in Falkovnia, legend has it the Horseman felt to the Talons, whereas in Barovia he was said to have taken his own life before Strahd's minions could get to him.

The First and the Last to Follow

Just because the Headless Horseman has passed does not mean the danger is over. The First to Follow, a mob of reanimated heads of the Horseman's past victims, usually swarm the survivors of the Horseman's attacks en masse. The truly unfortunate survivors of this second wave have to face a third wave of attacks from The Last to Follow. The Last to Follow is a group of flying reanimated heads but instead of normal humanoid heads, they are the heads of medusae and maedar.

Activities During the Grand Conjunction

The Headless Horseman played a strange and anomalous role in the Grand Conjunction. Apparently serving the interests of Azalin, the Horseman began riding around causing havoc in order to lure out a group of heroes who would ultimately be used by Azalin to manipulate Hyskosa's Hexad. The heroes were directed to fight the Horseman by Soldani, where they were ultimately defeated and decapitated, and their heads delivered to Azalin through unknown means.

As out of character as it is for the bogeyman-like Headless Horseman to seemingly work for another darklord's benefit, this was not the only anomaly. Instead of the usual Last to Follow, the final wave of the Horseman's barrage was a group of bounding beholders that finished off the last of the survivors of the Horseman's attack.

In Tales of Ravenloft

The Headless Horseman appears in the Tales of Ravenloft short story The Freak, where the Horseman doggedly pursues the disfigured hermit known as Anatole the Freak while at the same time seemingly acting as the poor soul's guardian.

In 4th Edition

In the 4th Edition Dragon Magazine article Domains of Dread: The Endless Road, the Headless Horseman is not a darklord but more a manifestation of a domain itself. The Headless Horseman wanders the Endless Road looking for prey and killing them as per standard Horseman behavior. It has effectively trapped the domain's true darklord, Eli van Hassen, in the van Hassen Estates that are warded against the Horseman. The Horseman rides upon Spitfire

Domains of Dread: The Endless Road also provides the Headless Horseman with a background. In life, he was a mysterious hero known only as the Horseman. He eliminated a hydra, earning the gratitude of the public and the love of Talitha van Hassen, Eli's daughter. As the Horseman overstayed his welcome, Eli van Hassen brought him to trial for the supposed rape of his daughter. Under pressure from Eli, Talitha bore false witness against her (now former) lover, the Horseman. The Horseman was summarily executed by decapitation. A week later the Mists enveloped the town, taking with it when it dispersed the van Hassen's and their servants. Overnight, the people had heard the sounds of galloping hooves, and in the morning the peasantry found their crop fields flattened.

Data from the Ravenloft Catalogue

		Darklords
		From the Shadows - p58 Download Now! Darklords - p6
		From the Shadows - p7 Download Now! Darklords - pp44-47
		Tales of Ravenloft:The Freak - pp222-250 From the Shadows - pp5-8 Download Now! Darklords - pp44-47
		Headless Horseman, The Headless Horseman