Legend of Sleepy Hollow
The Legend of Sleepy Hollow
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Washington Irving’s iconic tale of the Headless Horseman of Sleepy Hollow comes to life in this lyrical reimagining of the classic story.

Schools: This play is a good choice for schools.


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 19thcentury 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.

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 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 forThe 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.