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Small / Medium / Large Cast Versions

Soundtrack Cues ............ Script Sample

Small Cast (Touring) Version

Running Time: About 45-50 minutes
Flexible cast of 3: 2 Male, 1 Female
Easily adapted for larger cast

Lanky, pompous schoolmaster from Connecticut.
(Also plays Sleepy Hollow Boy briefly in opening.)

Coy young charmer, the subject of Ichabod's and Brom's adoring affection.
(Also plays Storyteller and others.)

Ichabod's roaring, roistering rival.
(Also plays Storyteller and others.)


Medium Cast Version

Running Time: About 45-50 minutes
Flexible cast of 9: 5 Male, 4 Female

Please contact: Dramatic Publishing


Large Cast Version

Running Time: About 45-50 minutes
Flexible cast of 22: 14 Male, 8 Female
Easily adapted for larger or smaller cast

ICHABOD CRANE: (M, 126 lines)
Lanky, pompous schoolmaster from Connecticut.
KATRINA: (F, 50 lines)
Coy young charmer, the subject of Ichabod's and Brom's adoring affection.
BROM BONES: (M, 66 lines)
Ichabod's roaring, roistering rival.
WASHINGTON: (M, 28 lines)  Storyteller.
IRVING: (M, 28 lines) Storyteller.
EMILY: (F, 35 lines)  Storyteller.
CHARLOTTE: (F, 35 lines) Storyteller.
GILES: (M, 26 lines) Storyteller.
FRAN: (F, 25 lines) Storyteller.
VAN TASSEL: (M, 10 lines) Katrina's father.
CLAUS: (M, 10 lines)  Sleepy Hollow Boy, Van Tassel's friend.
SEBASTIAN: (M, 4 lines) Sleepy Hollow Boy, Brom's gang.
ULRICH: (M, 5 lines) Sleepy Hollow Boy, Brom's gang.
NATHAN: (M, 5 lines)  Sleepy Hollow Boy, Brom's gang.
PETER: (M, 2 lines)  Schoolboy.
JUDITH: (F, 8 lines) Schoolgirl.
HANSEL: (M, 5 lines)  Schoolboy.
SADIE: (F, 4 lines)  Schoolgirl.
WILHEMINA: (F, 14 lines) Tea Lady.
GRETA: (F, 13 lines)  Tea Lady.
VAN RIPPER: (M, 7 lines) Horse Gunpowder's owner.
HEADLESS HORSEMAN: (M, 1 line, lots of action) 
Brom in disguise; may be played by another actor.

NOTE: With minor adjustments STORYTELLERS, SLEEPY HOLLOW BOYS, SCHOOL CHILDREN, and others may be played by male or female actors.  For a larger cast increase the number of actors in these groups. For a smaller cast some actors can play multiple roles. 

Headless Horseman Instructions Included!
Small & Large Cast One Act Halloween Plays for Children - The Legend of Sleepy Hollow Halloween Play - The Legend of Sleepy Hollow

The School Play Package for Large Cast Version includes instructions on how to make a fun, inexpensive Headless Horseman Costume!

Cues, sound effects, original background music

The CD Soundtrack contains special sound effects and background music (original music written for the play) that may be used to greatly enhance the performance. It does not contain music for the performers to sing along with. Cues have 10 seconds of silence at the end - times shown below include silence.
[ Click on [sample] to hear a short sample of the indicated cues ]

1.  FOREBODING / HAPPY MUSIC  (1:47) [sample]

2.  SCARY SOUNDS / HORSE  (1:43) [sample]

3.  SCARY STUFF  (1:54)

4.  KATRINA MUSIC  (0:32) [sample]


6.  ICHABOD SINGING MUSIC  (4:21) [sample]

7.  GUNPOWDER / HEADLESS CHASE  (2:26) [sample]

8.  CALMING MUSIC  (0:56)

9.  WEDDING MARCH (0:21)

10.  DANCE MUSIC / CURTAIN CALL  (1:28) [sample]

Note: Some teachers choose familiar songs, obtain sheet music and insert these songs into the play.  We recognize that each school has a wide variety of educational needs to fulfill and we invite you to be creative in your use of our scripts; including changes or additions that are appropriate for your students. As author/publisher of our own creative works, we do ask that you obtain proper copyright permission for any additions you might make - that responsibility is up to you.

Music & Sound Resources Available on the Internet
( Sheet Music, Song Books, CDs, DVDs, Sing-along, Karaoke, Sound Effects )

Excellent for Community Theatres!
Large Cast Play for Schools and Theatres - The Legend of Sleepy Hollow
Gaffney Little Theatre, SC

Large Cast Version

The fetching young Katrina has caused quite a rivalry between the new school master Ichabod Crane and the country swain, Brom Bones.  Brom has a clever plan for running the jittery teacher out of town.  It's a spooky Halloween night when he sets the scene for Ichabod's frightful ride home...

WASHINGTON: Along about midnight, after the ladies had retired, the men folk gathered...

IRVING: was their custom...

EMILY: ...around the fire to tell tales of ghosts and strange sights...

CHARLOTTE: the neighborhood is rich in legendary treasures of the kind.

(ICHABOD gathers, as if by a fire, warming his hands. He may be eating, but he obviously drinks in all BROM says. STORYTELLERS circle him when the speak as the SLEEPY HOLLOW BOYS did earlier.)

GILES: Many dismal tales were told about...

FRAN: ...funeral trains...


IRVING: ...and wailing were heard from the soul of Major André who haunts the place.

ICHABOD: Major André?

EMILY: There was also the story of...


BROM: (Moving in on ICHABOD.) ...the woman in white... she was often heard to shriek on winter nights before a storm, having died there in the snow.

ICHABOD: In... in the snow?

(BROM puts tablecloth on his head and shrieks -- scaring the daylights out of ICHABOD.)

BROM: (Getting cozy, sitting beside ICHABOD.) And then there’s my favorite story, Ichabod. The one about the Headless Horseman of Sleepy Hollow. Some of the folk around here say he was a German trouper. They say that during the Revolutionary War his head was carried off by a cannonball... (BROM uses a jack-o-lantern to represent the head and thrusts it toward ICHABOD.)  BOOM!

ICHABOD: (Jumping.) Do tell.

BROM: They say he rides at night as if on the wings of the wind. He rides back to the battlefield. (He brings the jack-o-lantern close to ICHABOD.) Guess what’s his favorite spot for haunting?

ICHABOD: I... I’m... sure I couldn’t say.

BROM: Remember the bridge, school teach? The church bridge?

ICHABOD: The ch-ch-church br-br-bridge?

BROM: Did you notice anything special about that covered bridge?

ICHABOD: It seemed... well... somewhat...

BROM: Somewhat... what?

ICHABOD: Well... just a touch... dark...

BROM: And?

ICHABOD: And frightening.


ICHABOD: (Shrieks.) Haunted! It seemed haunted!

BROM: (Smiling with satisfaction.) The church bridge is one of his favorite haunts, school teach. You’ll have to be careful going home tonight, Ichabod. Halloween is his favorite time of year. But don’t worry. Everyone knows – once you cross the bridge, you’re safe.

ICHABOD: (Cautiously relieved.) S-s-safe?

BROM: If you get across it before you meet the Headless Horseman. Good luck, Ichabod. (He leaves, exiting, laughing maniacally.)

(CHARLOTTE enters and "rebuilds" Gunpowder.)

CHARLOTTE: With a heavy heart and a worried soul Ichabod roused Gunpowder...

(ICHABOD gets on "horse".)

ICHABOD: Come on, boy.

CHARLOTTE: (Handing ICHABOD the reins/bucket rope handle.) ...and set out for home.

(OTHER STORYTELLERS enter, turn all the trees back to original positions, leaving the stark black silhouettes. Throughout the scene, they will perform the necessary sounds, trees, horses, etc., while using the cymbal for emphasis.)

GILES: All the stories of ghosts and goblins now came crowding into his mind.

ICHABOD: Major André...

FRAN: The night drew darker and darker.

ICHABOD: The woman in white!

WASHINGTON: The stars seemed to sink deeper in the sky. (Music becomes more ominous.)

ICHABOD: THE H-h-h-headless... (Can’t say it, gulps.) Horse... horseman. Oooh... Come on, Gunpowder. Come on, boy. (Gunpowder does not respond but continues in a plodding, rhythmic jaunt.)

IRVING: Soon he came upon the very spot where Major André was taken prisoner...

EMILY: ...a tree that had since been named, Andre’s Tree.

CHARLOTTE: (Moving tree to center of playing area, whispering.) Ich-a-bod! Ich-a-bod!

ICHABOD: (Dismounts, falls to his knees, pleading with the tree.) Major André? M-m-major... Major... I wish you no harm, sir, or ghost... uh... spirit. Please rest in peace, I only want to pass by. I do not wish to disturb your... uh... slumber, sir... uh... ghost-sir.

(CHARLOTTE tips Andre's Tree so that it leans over ICHABOD'S head. He looks up, cries out!)

GILES: Ich-a-bod!

ICHABOD: (Leaps back onto Gunpowder, closes his eye and prays.) Oh, please let me pass, oh please let me pass, oh...

(STORYTELLERS swirl trees swirl around him, then freeze. ICHABOD opens his eyes.)

There now, see, Gunpowder? Trees don’t move.

Note: This is a sample from the actual script.  To review the entire play, order the PERUSAL SCRIPT (online instant download). Or to save 20% on the full production kit and royalty for one performance, order the SCHOOL PLAY PACKAGE (below) and start rehearsals today!



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