Legend of Sleepy Hollow


Legend of Sleepy Hollow
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Schools: This play is a good choice for schools.

Washington Irving’s iconic tale of the Headless Horseman of Sleepy Hollow comes to life in this lyrical and literary reimaging of the classic story! Follow the affable schoolteacher Ichabod Crane as he endeavors to conquer his own fears and self-doubt in order to win the heart of the coquettish Katrina Van Tassel. Along the way, he’ll battle snot-nosed schoolboys, Brom Bones— the self-absorbed, self-proclaimed hero of the realm— and of course, the dominant specter of the land: the Headless Horseman.


Ichabod Crane has journeyed from bustling, high class Hartford, Connecticut, to the mild and tranquil Sleepy Hollow, New York, for the express purpose of serving as the town’s schoolmaster. He is boarded by Baltus 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, Icahbod 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 schoolmaster.



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 specter of Sleepy Hollow.

Casting Note:

Minimum Cast: 5 – 1 F, 3 M, 1 F/M.

Maximum Cast: 16 - 1 F, 3 M, 12 F/M (additional actors can be used as townspeople, school children, and the world of Sleepy Hollow— trees, scary things in the forest, etc.).

Suggested Actor Doubling for 5 Actors:

  • Storyteller 1/Katrina Van Tassel (F)
  • Storyteller 2/Baltus Van Tassel (M)
  • Storyteller 3/Brom Bones (M)
  • Storyteller 4/School Boy/Servant/Messenger (M/F)
  • Ichabod Crane (M)

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

Performance Royalties are based on theater particulars. Please fill out an application for a personalized quote.

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

Materials: your materials will be sent to you two months prior to your opening date and will include everything necessary for your production and can be ordered in Printed or Digital format. Printed Materials are provided on unbound three-hole punched loose-leaf paper while Digital Materials are provided via email as downloadable PDF files for you to print in-house. All materials are yours to keep! No deposits, no returns.

The required materials for The Legend of Sleepy Hollow include:
Production Scripts

Available Products:

Wicked Lit Print Edition - The beautifully designed anthology, available at wholesale costs to sell in your lobby!

Director's Script – Single-sided script with space for director’s notes.

Logo/PR Pack – Includes high-resolution artwork and reference photos. Also, ready-designed posters, reviews and pull quotes, if available.