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Ichabod Crane, “The Schoolmaster”

Ichabod Crane, "The Schoolmaster"
  • Alias: Ichabod Crane, also known as “The Schoolmaster”
  • Gender: Male
  • Race: Human
  • Occupation: Schoolteacher, storyteller, investigator of the supernatural
  • Religion: Devout Christian (Protestant), deeply superstitious
  • Allies: Students, fellow teachers, local townsfolk who believe in his teaching methods and appreciate his knowledge
  • Enemies: The Headless Horseman, superstitious individuals who question his teachings and view him as an outsider
  • Abode/Base of operations: Ichabod Crane resides in a small cottage near the Sleepy Hollow School, serving as his home and base of operations.
  • Nationality: American
  • Languages: English
  • Alignment: Lawful Good
  • Affiliation(s): Sleepy Hollow School, Sleepy Hollow community, local church
  • Significant others: Katrina Van Tassel, a beautiful and wealthy young woman he is infatuated with. However, their relationship remains complicated and uncertain.

In the quaint town of Sleepy Hollow, Ichabod Crane, a lanky and bookish schoolteacher, leads a life immersed in mystery and the pursuit of knowledge. With his wide-brimmed hat, spectacles perched upon his nose, and a perpetual air of curiosity, Ichabod is known for his sharp intellect and insatiable appetite for unraveling the enigmatic.

Driven by a deep fascination with the supernatural and an unyielding desire to uncover the truths that lie beyond the mundane, Ichabod finds himself drawn to the eerie legends and folklore that shroud Sleepy Hollow. As the town’s schoolteacher, he not only imparts knowledge to young minds but also serves as a guardian of the town’s history and secrets.

With each moonlit night and whispered tale, Ichabod becomes more entangled in the web of supernatural occurrences that grip Sleepy Hollow. His relentless pursuit of truth and his unwavering determination to protect the town’s inhabitants from the forces of darkness make him a valiant defender against the unknown.

While Ichabod’s slender frame may not possess the brawn of a warrior, his quick wit and resourcefulness compensate for any physical limitations. Armed with his trusty school cane, which doubles as a weapon in dire situations, he faces the supernatural threats that emerge from the shadows.

Ichabod’s ultimate goal is to unveil the mysteries that shroud Sleepy Hollow and shed light on the dark secrets that haunt its inhabitants. Through his scholarly expertise, astute observations, and unwavering courage, he strives to restore peace and tranquility to the once serene town.

As Ichabod Crane ventures deeper into the realm of the uncanny, his journey intertwines with the legends of Sleepy Hollow, and his own destiny becomes forever entwined with the enigmatic forces that lurk within.

Ichabod Crane, The Schoolmaster

Ichabod Crane, The Schoolmaster

Medium humanoid (human), lawful good

Armor Class: 12 (unarmored) Hit Points: 65 (10d8 + 20) Speed: 30 ft.

10 (+10)12 (+1)14 (+2)16 (+3)18 (+4)14 (+2)

Saving Throws: Wisdom +7, Intelligence +6 Skills: History +6, Investigation +6, Perception +7 Senses: Passive Perception 17 Languages: Common Challenge: 5 (1,800 XP)


School Cane. Melee Weapon Attack: +4 to hit, reach 5 ft., one target. Hit: 4 (1d4 + 2) bludgeoning damage. On a hit, the target must succeed on a DC 15 Constitution saving throw or be stunned until the end of its next turn.

Investigative Insight (3/Day). As a bonus action, Ichabod Crane can make an Intelligence (Investigation) check to gain insight into his surroundings. He has advantage on the check.

Superstitious Charm. Once per long rest, Ichabod Crane can cast the spell Protection from Evil and Good.


Evasive Maneuver. When a creature makes a melee attack against Ichabod Crane, he can use his reaction to impose disadvantage on the attack roll.

Lair Actions:

Supernatural Knowledge. Once per round, Ichabod Crane can use a lair action to force all creatures within 30 feet of him to make a DC 15 Wisdom saving throw or become frightened until the end of their next turn.

Legendary Actions:

Ichabod Crane can take 2 legendary actions, choosing from the options below. Only one legendary action option can be used at a time and only at the end of another creature’s turn. Ichabod Crane regains spent legendary actions at the start of his turn.

  • Attack. Ichabod Crane makes one melee weapon attack.
  • Investigative Insight. Ichabod Crane uses his Investigative Insight ability.
  • Move. Ichabod Crane moves up to his speed without provoking opportunity attacks.


  • School cane
  • Book of local legends and folklore
  • Traveler’s clothes
  • Backpack with various supplies and personal effects

Ichabod Crane, the Schoolmaster, wields a sturdy school cane as his weapon, a symbol of his authority and discipline. He combines his knowledge of history, keen investigative skills, and a touch of the supernatural to protect those around him. With his cane in hand, he delivers precise strikes to his opponents, using its stunning effect to disable and control his enemies. Despite his scholarly demeanor, Ichabod is not afraid to face the dangers that lie ahead, striving to uncover the truth and ensure the safety of those he cares for.

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