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A PLAYSCRIPTS TITLE
Short Play, Comedy / 8w, 7m, 9 any gender (youth) plus ensemble
Tracy Wells
This adaptation of Washington Irving’s classic tale brings the eerie charm of colonial America to life in a spooky and delightfully witty stage production. Filled with lively townsfolk, laugh-out-loud moments and a chilling climax, this adaptable play – shortened to a one-act version – offers multiple endings to suit audiences of all ages.
The Legend of Sleepy Hollow, adapted by Tracy Wells from Washington Irving’s classic tale, brings the eerie charm of colonial America to life in a spooky and delightfully witty stage production. When quirky schoolmaster Ichabod Crane arrives in the mysterious village of Sleepy Hollow, he hopes to find purpose, community, and maybe even love. But whispers of a fearsome ghost – the Headless Horseman – haunt the woods, and Ichabod quickly finds himself entangled in the disappearances of neighbours, supernatural intrigue and a romantic rivalry over the beautiful and intelligent Katrina Van Tassel. Filled with lively townsfolk, laugh-out-loud moments and a chilling climax, this adaptable play offers multiple endings to suit audiences of all ages.
This version has been condensed to a one-act version for all of the same spooky, delightful wit in a shorter evening.
A full-length version of this play is also available.
The Legend of Sleepy Hollow premiered in Shelby Township, Michigan with Eisenhower High School’s 25th Street Players on 24 October 2025.
ICHABOD CRANE – Lanky and quirky schoolmaster, male. KATRINA VAN TASSEL – A beauty who’s more than meets the eye, female. BROM BONES – Ichabod’s brutish rival, male.
Ensemble TAVERN WAITRESS/BARMAN – Any gender. TAVERN DWELLERS – At least two, any gender. DIEDRICH/DEIRDRA – Traveler, any gender. STORYTELLER – Teller of tales, male. WIDOW JANSEN – Iris/Otto’s mother, female. ESMEE, AGATHA and MARGRIET – Presumed witches, female. SELECTMAN FABER – Town selectman, male. CONSTABLE HENDRIKS – Sleepy Hollow constable, male. BEATRIX, ALETA and GERTIE – Young ladies looking for love, female. LADY VAN TASSEL – Katrina’s wealthy and doting mother, female. LARS – Sleepy Hollow Boy and Brom’s friend, male. IRIS/OTTO JANSEN – Student and self-proclaimed apprentice, any gender. JOZEF/JOANNA, XANDER/ZARA and FLEUR/FLORIS – Ichabod’s students, any gender. STUDENTS – Additional students, any gender. TOWNSPEOPLE – As many as you would like, any gender. HEADLESS HORSEMAN – The headless ghost of a Hessian soldier, male.
ON CASTING There are many opportunities to double roles. The only roles that should not be doubled are Ichabod, Kartina and Brom.
Several roles are listed as flexible gender and alternate names are provided. A gender and name and all associated pronouns were chosen for the script, however for those characters, please choose a gender and name and make changes to any pronoun or gender references as needed.
Additionally there are several lines designated as TAVERN DWELLER, TOWNSPERSON or STUDENT – some are ad-libbed lines and some are listed. You may distribute those lines as you see fit. For TAVERN DWELLERS, I recommend having at least three, but you can have as many as you’d like. For the TOWNSPERSON or STUDENT lines, you can have as many as you’d like, or if you do not have additional STUDENTS or TOWNSPEOPLE outside of those named in the character list, then you may distribute those lines any named STUDENT or TOWNSPERSON as you see it.
The small, secluded village of Sleepy Hollow, surrounded by woods. 1790.
An Interview with Tracy Wells – The Scene Podcast
Tracy Wells has loved seeing stories come to life on stage for as long as she can remember. In high school, she was able to tread the boards herself in a few starring roles in her drama department. Alas, like her character in A Chorus Line, Kristine, she couldn’t really sing, ...