Legend(s) of Sleepy Hollow
Legend(s) 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 school master. 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, 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 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 by 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 of 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

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.

Thirty-six of Jonathan's plays have been produced at site-specific locations, schools and theatres around the world including 27 Ways I Didn't Say “Hi” to Laurence Fishburne (Actors Theatre of Louisville - Humana Festival, Milwaukee Rep - RepLab), Grandpa and the Gay Rabbi (Winner – 2016 Samuel French Off-Off Broadway Play Festival), 30K Arabian Nights (San Jose Rep - SJREAL), The Legend(s) of Sleepy Hollow (Chance Theater) and The Giant and The Pixie (Chance Theater, New York SummerFest). Jonathan is the Executive Director of Unbound Productions in Los Angeles and is one of the co-creators of the multi-award winning immersive theatre events Wicked Lit, History Lit, and Mystery Lit. Plays written for Unbound include The New Catacomb, Las Lloronas, The Grove of Rashomon, Anansi and the Demons (Mountain View Mausoleum and Cemetery); The Garden Party and The Girl Who Owned a Bear (Pasadena Museum History); and Holmes, Sherlock, and The Consulting Detective (Los Angeles County Arboretum). Jonathan received an Individual Artist Award from the Pasadena Arts Council, is a five-time Finalist for Actors Theatre of Louisville's Heideman Award and has been named a Finalist for both the O'Neill National Playwrights Conference and the City Theatre National Short Play Award. His work has been recognized by the CTG/Humanitas Prize (Semi-Finalist), NuVoices at Actors Theatre of Charlotte (Semi-Finalist), the William Inge Theatre Festival (Short Play Lab), the Great Plains Theatre Conference (Short Play Lab), and the Heartland New Play Festival (Festival Winner). Fourteen of Jonathan’s plays are published by Steele Spring Stage Rights, Samuel French, YouthPLAYS, PlayScripts, Applause Theatre & Cinema Books, and Original Works Publishing. He is a proud member of Playground-LA’s Writer’s Pool, the Antaeus Playwrights Lab, the Dramatists Guild of American and a Lifetime Member of the Alliance of Los Angeles Playwrights. B.A. in Theatre: Playwriting from UCSD. [jonathanjosephson.com]

Performance Royalties for AMATEUR and EDUCATIONAL Groups begin at $90.00 per performance for theaters under 150 seats, and rise depending on ticket prices and theater particulars. 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. 
An Authorized Materials/Rehearsal Package 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

An Authorized Materials/Rehearsal Package must be purchased from Stage Rights as a part of your licensing agreement. Your materials will be sent to you two months prior to your opening date, unless other arrangements have been made in advance with your Stage Rights Licensing Representative.
The Authorized Materials/Rehearsal Package for Legend(s) of Sleepy Hollow consists of:
14 Production Scripts / $170.00 (shipping included)
Production Scripts for Plays are professionally printed and bound with a full-color cover.
You will have the option to purchase additional Production Scripts at a discounted rate when you complete your Licensing Agreement.
Official Logo Pack Now Included! To help you promote your show, Stage Rights now includes a logo pack with your license. The logo pack includes high resolution versions (both color and black and white) of our show logo. The logo is the portion of the artwork with the title of the show. The surrounding artwork is also available for an additional fee.
Optional Materials:
Stage Manager’s Script – Printed on standard 8.5” x 11” 3-hole-punched paper, with the same page numbers and text as the Printed Production Scripts, but with more space on the page for notes and cues.