Halloween Plays and Scripts for Kids, Schools & Theatres!

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The Legend of Sleepy Hollow - Halloween Play for Kids!

One Act Plays for Middle Schools!"The Legend of Sleepy Hollow has been very successful. Probably one of the most popular productions we ever had here in our Youth Theatre!"

Joe Lauderdale The Laguna Playhouse, CA

Children's Halloween Play - The Legend of Sleepy Hollow

Halloween Play for Middle Schools! Producers, this fast-paced script follows the familiar story as you know it and Washington Irving wrote it.

 The Legend of Sleepy Hollow

Halloween Play for Middle Schools! There are no unexpected story tangents, just the famous spine-tingler with lots of suspense and uproarious comedy! 

 Halloween Play - The Legend of Sleepy Hollow

One Act Plays for High Schools!"A delightful show that packed the house. Enjoyed by children of all ages.

 Sheila Freudenberger, Orange Curtain, San Juan Capistrano, CA

The Legend of Sleepy Hollow

Halloween Play for Middle Schools! "We had to add three performances to accommodate all those schools who wanted to come. One parent told me it was their best field trip so far."

Becki Bradford, Chattanooga State Drama Club, Chattanooga, TN

Children's Halloween Play - The Legend of Sleepy Hollow

Halloween Play for Middle Schools! "Preschool through sixth grade students were in awe of Ichabod and Katrina. The characters' interaction with the audience brought Sleepy Hollow right into their hearts."

Hayes Elementary School

One Act Halloween Play - The Legend of Sleepy Hollow

Halloween Script for Schools! "Six out of six sold out performances in our 1300 seat theatre! The children loved the Headless Horseman!"

Paramount Arts Center, Ashland, KY

 Spooky Halloween Fun for Kids!

Halloween Play for Middle Schools! Can be performed by as few as 3 or more than 20, for touring or mainstage.

Halloween Play - The Legend of Sleepy Hollow

Halloween Play for Middle Schools! The script includes instructions on how to make an inexpensive headless horseman!

Halloween Play - The Legend of Sleepy Hollow

Halloween Play for Middle Schools! Great One Act Play For Middle Schools & Drama Clubs! High Schools and Community Theatre Productions! The script can be easily adapted for a larger cast!

Halloween Play - The Legend of Sleepy Hollow

Halloween Play for Middle Schools! Minimal props & tech keep your production clever & fast-paced!

Halloween Play - The Legend of Sleepy Hollow

Halloween Play for Middle Schools! "Simple to stage and popular with audiences due to plenty of comedy!"

Rachel King, Spotlites Youth Theatre, Chatham, Kent, UK



The Legend of Sleepy Hollow
One Act Touring Play for Schools and Theatres

Cast List
CD 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.

Large Cast of Kids - Legend of Sleepy Hollow!
Corsicana Children's Theatre, TX

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.

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

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


Easy Choice! Top Quality! All of these plays were professionally developed by ArtReach Touring Theatre or were commissioned by Professional LORTS like Florida Rep and Rep of St. Louis.  All have had professional tours to theatres and schools across the country.  Many have won awards in High School One Act Play Contests, Drama and Thespian Speech and Theatre Competitions.

Easy Staging and Travel!  Competitions rarely take place on your own stage!  These One Act Plays have been designed to travel to the Contest Host Theatre on that important competition day. All have easy staging, simple sets & costumes, minimal props, flexible tech for a mainstage or gym/open facility performance space.  At last your students can worry about their performance, not the set!

Easy to Adapt with Flexible Casting!  When you license any of our One Act Plays you have permission to cut, adapt and adjust cast size!  You also have permission to make a video or DVD of the production!  At last, you are allowed to adapt a play to your students' needs!

Easy Budget!  These One Act Plays, can be successfully produced on limited budgets and by small or medium student casts with little or no tech assistance.  Many have great background CDs for an easy, inexpensive professional touch! 

Easy Ordering!  Follow the steps to order and pay your royalty, once you've paid,  you're good to go!  No complicated applications and the endless trouble of getting permission to make changes for your students' needs!

Tried and True!  Our One Act Plays have been performed literally thousands of times by many professional theatres such as Stella Adler Theatre, Solano Youth Theatre, Nebraska Theatre Caravan, Singapore Repertory Theatre, George Street Players, Fulton Theatre Company, Indiana Repertory Theatre, Boarshead Theatre, Virginia Stage, Honolulu Theatre for Youth, Kennedy Center and Sundance Children's Theatre, to name a few.  High Schools, Junior Highs, Middle Schools have been performing these plays for over 30 years!

Kathryn Schultz Miller is one the most prolific and most produced playwrights for children.  Her script, A THOUSAND CRANES, won the National Endowment for the Arts Playwright Award (and countless others) at a time when plays for children were not considered serious works. Now, many of her published scripts are considered classics for young audiences.  When teachers voiced their need for great plays that kids can perform Ms. Miller responded with ArtReach’s School Plays:  “I never dreamed I’d write for anyone other than professionals.  But writing for child performers has been the most profound and rewarding experience of my life”.

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 Legend of Sleepy Hollow
Gaffney Little Theatre, SC - DCP Theatre, Telford PA

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: ...as was their custom...

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

CHARLOTTE: ...as 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).

Looking for large cast plays & musicals for your students to perform?
We have scripts written just for you! Click on any title below...

A Christmas Carol * A Christmas Cinderella * A Christmas Peter Pan
A Christmas Wizard of Oz * A Snow White Christmas * A Thousand Cranes * Aladdin
Alice in Christmas Land * Alice In Wonderland * Beauty and the Beast * Cinderella
 Emperor's New Clothes * Jack and the Beanstalk * Jungle Book * Kid Frankenstein
Legend of Mulan * Legend of Sleepy Hollow * Little Mermaid * Peter Pan * Pinocchio
Princess and the Pea * Reluctant Dragon * Sleeping Beauty * Snow White
Treasure Island * Twas the Night Before Christmas * Velveteen Rabbit
We Are The Dream * Wizard of Oz * El Mago de Oz (Spanish Wizard of Oz)
Children's Christmas Plays & Children's Christmas Musicals

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