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!