Legend(s) of Sleepy Hollow


Legends of Sleepy Hollow
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You know one version, the popular version, of Washington Irving’s tale of the Headless Horseman of Sleepy Hollow— but wouldn’t you like to know what really happened on that fateful night that Ichabod encountered the Horseman? This play reveals all from the point-of-view of the one character who was there and knows the whole truth: Ichabod Crane’s horse, Gunpowder.


Ichabod Crane has journeyed from Connecticut to Sleepy Hollow, New York, for the express purpose of serving as the town’s schoolmaster. He is boarded by Baltrus Van Tassel, a substantial Dutch farmer, and father to Katrina Van Tassel, a blooming lass of fresh 18. Ichabod quickly falls for the beautiful Katrina and endeavors to win her heart— but Brom Bones, the Bully of Sleepy Hollow, also has his eyes set on Katrina (as well as her father’s substantial wealth). It becomes known that Ichabod loves ghost stories, but that they also terrify him to his core. At a party, Brom boasts that he recently defeated the local ghost— the Headless Horseman of Sleepy Hollow— in a race that ended at the local church bridge; Ichabod is entranced by the story. On his way home, astride the old horse Gunpowder, Ichabod encounters the Headless Horseman, who begins to chase him! Ichabod flees from the Horseman until he and Gunpowder reach the supposed safety of the churchyard— but they’re not safe at all. The Horseman hurls his cursed cranium at the affrighted pedagogue, who tumbles off Gunpowder in a heap. The old horse flees, as does the Horseman. The next day, Ichabod is gone, with only Gunpowder’s brown saddle and curious teething of the remains of a broken pumpkin to give the townspeople any clue as to what happened to the unfortunate school master.

AND THEN… Gunpowder himself enters. He tells the audience that none of this is really what happened— well, that it is what happened, but not why it happened. He then restarts the story from the top to clarify a few things. First, Ichabod was recruited to Sleepy Hollow by Baltrus in order to pursue Katrina— Baltrus wanted a good man, and not Brom, to marry his daughter. Brom found out about that plot and threatened to kill Ichabod if Baltrus didn’t find a way to make this right. So Baltrus came up with the plan of disguising himself as the Horseman to chase off Ichabod— which is what he did. Brom married Katrina, and hopefully Ichabod survived to live another day, teaching other children the wonder of the world.


The Legends of Sleepy Hollow delivers the Halloween chills!

–Hollywood Gothique


Storytellers 1-4 (F/M) – The voices and setting of Sleepy Hollow (roles can be divided in half).

Ichabod Crane (M) – A Connecticut Schoolmaster— very friendly, huge appetite.

Katrina Van Tassel (F) – A fair damsel, a bit of a coquette.

Baltus Van Tassel (M) – Katrina’s father, a wealthy farmer.

Brom Bones (M) – The self-proclaimed hero of the country round.

School Boy (F/M) – A jerky kid with a secret.

Servant (F/M) – A wise and loyal bodyguard.

Messenger (F/M) – A cranky deliverer of news.

Headless Horseman (F/M) – The terrifying spectre of Sleepy Hollow.

Gunpowder (F/M) – Ichabod’s loyal and energetic horse.

Suggested actor doubling for 6 actors:

  • Storyteller 1/Katrina Van Tassel
  • Storyteller 2/Baltrus Van Tassel
  • Storyteller 3/Brom Bones
  • Storyteller 4/School Boy/Servant/Messenger
  • Ichabod Crane
  • Gunpowder

Minimum cast: 6 – 1 F, 3 M, 2 F/M
Maximum cast: 17 - 1 F, 3 M, 13 F/M (additional actors can be used as townspeople, school children, and the world of Sleepy Hollow— trees, scary things in the forest, etc.)


The play takes place in numerous settings throughout early 19th century Upstate New York. The settings include a school house, the Van Tassel Mansion, several country roads, a glen, and the route where Ichabod is chased by the Headless Horseman.

Performance Royalties for AMATEUR and EDUCATIONAL Groups, please fill out an application for your personalized quote.

Performance Royalties for PROFESSIONAL Theaters will be quoted as a box office percentage, with a minimum guarantee based on ticket prices and theater particulars. Please fill out an application for your personalized quote.

Authorized Materials must be purchased from Stage Rights as a part of your licensing agreement (see Materials).

Billing responsibilities, pertinent copyright information, and playwrights' biographies are available in the show rider that comes with your license agreement.

"The Legend(s) of Sleepy Hollow delivers the Halloween chills!" —Hollywood Gothique

Authorized Materials must be purchased from Stage Rights as a part of your licensing agreement. Your materials will be sent to you digitally by your Licensing Representative.

The Authorized Materials/Production Package for The Legend(s) of Sleepy Hollow are all fulfilled digitally and consist of:

Acting Edition

Stage Manager Script