Sleepy Hollow: The Musical


Sleepy Hollow
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This rethinking of Washington Irving’s classic short story casts Ichabod Crane as the villain of the piece and provides the backstory of the town of Sleepy Hollow complete with sorcery and dark secrets. The stirring music, magical effects, and intriguing plot twists transform this familiar legend into a powerful theatrical experience.


Act I

Prologue: The Bridge – The play opens as the most recent schoolmaster of the town of Sleepy Hollow, Bastian Onderdonk, is attempting to leave and cross the bridge that links the village to the outside world (“Prologue”). Despite their protestations, he departs, declaiming their madness and the supernatural forces at work in the town. As he crosses the bridge, it retracts leaving the citizens of Sleepy Hollow isolated and trapped.

Scene 1: The Village Green – Abraham “Brom” Van Bron, the town carpenter of Sleepy Hollow, is busily at work repairing a rocking horse for Mina Van Ripper, who is there watching with her brother, Dirk. After a bit of teasing from Dirk, Mina runs off to tell her mother, and Brom and Dirk discuss the impending arrival of a new schoolmaster. Katrina Van Tassel, daughter of the town’s wealthiest farmer, enters and overhears them as they talk about how all of the single women will be chasing after the new teacher. Brom finishes the rocking horse and gives it to Dirk, who leaves. Once alone, Brom and Katrina begin to flirt with one another, and it is revealed that they are secretly betrothed (“A Lovely Afternoon”). Various other citizens stroll by, including widow Gusta Tenbrook and her three children, Dorine, Willem, and Anika, followed by Sabine Vedder, the town spinster. Just as Brom and Katrina are about to steal a kiss, their best friends, brother and sister Faas (the town cobbler) and Rosalie Brinkerhoff, arrive and tease them playfully. As they exit, Zander DeGroot, farmhand of Katrina’s father, passes by, after which Brom and Katrina finally get their kiss. The Tenbrook children return and talk to Katrina about getting ready to meet the new schoolmaster, as well as the many legends surrounding Sleepy Hollow, including “the curse.” Suddenly, Willem spots the new teacher approaching in the distance. As the various citizens of the town (including Dirk and Mina’s parents, Hans and Arabella Von Ripper) gather on the green to meet him, we see that Gusta, Sabine, Rosalie, and Arabella have all baked items for the schoolmaster to welcome him (“All That We’ve Longed For”). At the conclusion of the song, Ichabod Crane, the new schoolmaster, arrives. He is impressed by their greeting and accepts the baked goods with relish, particularly Rosalie’s gingerbread. After introductions, he announces that school will begin promptly in the morning and, horrified to learn that there is no church choir, declares himself the new choirmaster and schedules a rehearsal the next night. Hans, the local stable master, informs Ichabod that he will be living with his family and prepares to take him to their home. Before he does, Ichabod mentions that he ran into Bastian Onderdonk, his old university rival, who despite their previous friction had told Ichabod that he thought he’d be a perfect fit for Sleepy Hollow. During this speech, unseen by Ichabod, a pair of shoes slung over Faas’s shoulder levitate and drift away. The villagers keep Ichabod distracted from this situation and it goes unnoticed.

Scene 2: The Schoolhouse – Ichabod enters to find the schoolroom in disarray, quickly tidies things up, and begins writing on the chalkboard. The Tenbrook and Von Ripper children noisily arrive and Ichabod silences them with a large brass bell and they take their seats. After the children introduce themselves, Ichabod lays down his strict rules and demanding expectations (“Never Spare the Rod”). The children are horrified at his brutal attitude and begin planning a revolt. As they begin their reading assignment, several books on the shelf behind Ichabod mysteriously slide to one side all by themselves. When asked what happened, the children seem unruffled and explain that it must have been poltergeists. Ichabod dismisses that notion as rubbish, but a moment later a pile of books crashes to the floor. Ichabod, now on edge, demands an explanation, and the children tell him about the curse on Sleepy Hollow (“Heads or Tails”). Ichabod declares blasphemy and begins brandishing a book decrying the evils of witchcraft. As he does so, more books tumble from the shelves, the pen on his desk rises and begins writing by itself, and the blackboard begins to spin. Ichabod dismisses school, and they all flee the classroom, the children laughing and Ichabod shrieking in fear.

Scene 3: The Church – As the townspeople arrive for choir practice, Dorine is regaling Gusta, Sabine, Arabella, and Hans with an account of what happened that morning at the school. Faas, Rosalie and Katrina enter as Faas recounts seeing Ichabod running from the school in hysterics and begins imitating him just as Ichabod walks in. Ichabod quickly assumes control and begins warming up the choir. As he does so, a disembodied voice echoes from somewhere within the church. After several occurrences, Ichabod demands an explanation, which the villagers try to dismiss as the natural acoustics of the building. Brom and Zander then enter late, much to Ichabod’s chagrin, and rehearsal begins with Dorine playing the organ (“This Season of Abundance”). During the song, Ichabod begins moving from woman to woman, touching them in an effort to coach their singing. The men take strong offense to this and grow increasingly irritated as the song reaches a climax. Ichabod dismisses the rehearsal and pulls Katrina aside to introduce himself and praise her singing. Brom inserts himself into their conversation. Katrina, seeing the rivalry that has developed, laughingly excuses herself and exits with Rosalie, leaving Brom and Ichabod alone for a moment of verbal sparring before Brom departs.

Scene 4: The Village Green – The children and adults gradually gather, comparing stories of Ichabod’s actions in the schoolroom, church, and village. It soon becomes clear that the town is becoming divided in their opinion of the schoolmaster with Sabine, Arabella, Gusta, and Katrina coming to his defense while the others berate him (“A Conundrum”). At one point, Ichabod passes by reading a book, and the townsfolk all fall silent until he has leaves. After the song, Faas and Rosalie tease Katrina about her engagement and, seeing that Ichabod is returning, Katrina quickly exits with Zander to return home. Ichabod enters looking for Katrina and is informed that he just missed her. As everyone disperses, Ichabod retains Anika and asks her to give a sealed note to Katrina. After hinting that her mother has told her that she has to be nice to Ichabod so he won’t leave and the curse will be lifted, she agrees to take the letter and, as she is leaving, sees Brom approaching and asks him to pass the note from Mr. Crane along to Katrina. Brom accepts it willingly and glares at Ichabod. Brom opens the letter and reads it in front of Ichabod, fuming at its cloying and aggressively romantic contents. As Ichabod tries to leave, Brom bars his path and the two have a verbal showdown, each declaring their own intentions for Katrina (“The Best Man”).

Scene 5: The Exterior of the Van Tassel Estate – As Ichabod approaches the Van Tassel house, he encounters Zander laboring in the garden where a large scarecrow stands guard. He inquires as to whether Katrina is at home and is rebuffed and warned that if he continues to pursue Katrina, Brom will take action. Zander leaves and Ichabod knocks on the door and is greeted by Balthus Van Tassel, Katrina’s father. Balthus greets him warmly and refers to the challenge they’ve had replacing Diedrich Knickerbocker, their longtime schoolmaster. He also invites Ichabod to join them at his estate for the town’s annual Halloween party. Ichabod notices the expansiveness of the Van Tassel estate and begins to investigate its full breadth. As Balthus regales him with details about his abundant livestock, acreage, produce, and beautifully appointed mansion, Ichabod’s inherent greed begins to rise within him and his intentions for Katrina’s hand become rabid. Katrina returns home and, despite her protestations, is left alone with Ichabod by her father so that she and Ichabod can become better acquainted. Ichabod unexpectedly begins proposing to her, and as she resists, he informs her that he has become aware of the curse and threatens Katrina, telling her that he will only remain if she marries him. She explains the true nature of the curse and its accompanying riddle. As Ichabod becomes increasingly aggressive, she threatens to call for her father, but Ichabod issues a harsh warning. She asks him to leave and he obliges. Left alone, she reflects on her dilemma and what her personal sacrifice in marrying Ichabod could mean for the ultimate fate of Sleepy Hollow (“Beyond the Hollow”).

Scene 6: Van Ripper’s Stables – In an attempt to encourage Ichabod to stay in Sleepy Hollow, Hans offers him the use of one of his horses. Ichabod expresses his appreciation but is vexed when he is presented with Gunpowder, a broken down old nag. Despite his protestations, Hans assures him that it’s a good horse and leaves. Alone, Ichabod acknowledges the shoddy treatment he is being given by the town and vows to take matters into his own hands (“Ichabod Redux”).

Scene 7: The Great Hall of the Van Tassel Estate/The Woods – The entire village has gathered for their annual Halloween party and, prior to Ichabod’s arrival, Balthus reminds them of the importance of treating the schoolmaster to a wonderful evening. As Ichabod enters, everyone begins a spirited dance during which partners are changed and Ichabod and Brom are in constant competition for Katrina. This continues after the dance with Ichabod making further threats to Brom. Sabine makes a play for Ichabod’s attentions but is rebuffed. Hans calls for everyone’s attention and everyone assembles for the annual telling of the town’s “Halloween Tales” making Ichabod the guest of honor and target of their stories (“Upon…”). They recount incidents that include: a scarecrow coming to life and wreaking havoc on the town, a young girl having a fit of madness and floating off into the night sky, fiery demons bursting from a family’s hearth, a parson who vanished from the steeple of his church during a lightning storm, and a young bridal couple who were attacked when the bride’s twin sister, a suspected witch, blocked them from leaving Sleepy Hollow on their wedding night. The following morning, the bride awoke to find herself beside the body of her headless groom. As the song concludes, Ichabod berates the villagers for trying to scare him with their nonsensical superstitions. He becomes increasingly insulting until Balthus snaps and angrily tells him that they are not legends but the actual history of their town. They explain how all of the victims were members of their various families and, although he tries to apologize and remind them of how much they need him to break the curse, they expel him from the party and their town. The action segues to the exterior where Ichabod mounts Gunpowder and prepares to depart once and for all. As they ride deeper into the woods, Ichabod becomes increasingly unnerved until suddenly the Headless Horseman appears, brandishing a long sword. A chase begins until they pass one another and Ichabod knocks the Horseman from his steed with his book on witchcraft that he had been using as a shield. As the Horseman, topples to the ground, his disguise falls away, revealing Brom as the perpetrator of the charade. Ichabod picks up Brom’s sword and is about to strike when the real Headless Horseman appears wielding a glowing Jack-o-lantern. Ichabod and Brom quickly remount their horses and the chase resumes in greater desperation and earnest. At last, Ichabod and Gunpowder gallop across the bridge but the Horseman hurls his pumpkin after them which bursts into flame. As the bridge retreats and silence falls, Brom and the Horseman regard one another. The Horseman bows and gallops off into the night as the curtain falls.

Act II

Scene 1: Two Dressing Areas in Sleepy Hollow/The Village Green – It is Brom and Katrina’s wedding day, and the two are being attended by Faas and Zander, and Arabella and Rosalie, respectively (“This is the Day”). The women sing with joyful anticipation of the event as Faas and Zander jibe Brom about the gloom and doom ahead. They segue to the village green, where Balthus awaits to perform the ceremony. Brom and Katrina speak their vows (“Your Heart With Mine”), and a wedding dance ensues, during which Rosalie suddenly becomes disoriented and begins launching verbal attacks on everyone (“Rosalie”). Faas and Zander subdue her and lead her off toward home. As the townspeople try to make sense of what just happened, they realize that Rosalie had been eating gingerbread which none of them had brought to the wedding.

Scene 2: The Exterior of the Van Tassel Estate – The wedding couple and guests have arrived for a celebratory feast, and congratulatory wishes are being offered. Several of the children gather and talk about how Rosalie had acted just like the girl who flew away in the Halloween tale. Faas enters with a somewhat shaken Rosalie, and the adults prepare to drink a toast to Brom and Katrina with a special wine. Dirk begs to have some but is told to wait until he is older. He indicates that there is an extra glass, causing everyone to realize that Zander is missing. As everyone exits to search for him, Dirk lingers behind and samples the wine. As he does so, the scarecrow in Van Tassel’s garden begins to twitch and moan. Dirk cries out for his parents who return with the other guests. When he tells them about the scarecrow, they suspect that he has drunk some of the wine and is having a reaction, but the scarecrow suddenly lurches. Brom runs to the scarecrow and removes its hat and head, revealing a groggy Zander. He is helped down with the aid of Hans and Faas and struggles to tell everyone about how he was hit from behind, given something to drink, and been left hanging in the garden for hours (“Zander’s Lament”). The villagers try to make sense of what is going on when suddenly Willem suggest that perhaps Ichabod has returned. They realize that no one has visited the schoolhouse since his departure and that he may be hiding there. Brom, Faas, and Hans all leave to check out the school, and a few moments later, Dorine begins to smell smoke. They look off in the direction of the Von Ripper home and stables and see that the sky is turning orange. They all run off with the exception of Katrina and Sabine, who try to comfort a hysterical Rosalie.

Scene 3: The Schoolhouse – Brom, Faas and Hans enter to find the schoolroom in disarray with all of the desks piled into a central barricade and papers strewn everywhere. The men try to determine whether or not the curses have returned or whether Ichabod is indeed behind all of this. Suddenly, Arabella, Mina, and Dirk burst in distraught because their home and stables have burned to the ground. Arabella verbally attacks Brom, saying that he and Katrina were responsible for bringing back the curse because they had defied its conditions and gotten married (“Unraveling”). As they sink against the pile of desks in despair, they suddenly come crashing to the ground, where Dirk finds Ichabod’s book on witchcraft, proving that he has indeed returned. Eager to show this evidence to the others, they head for the church to ring the bell and gather the town.

Scene 4: The Church – The group from the schoolhouse has arrived and is trying to sort through the evidence as Katrina and Sabine rush in, followed a few moments later by Zander and Balthus. They realize that the Tenbrooks haven’t arrived, and just as Faas starts to leave, he is confronted by a silent Gusta. She is in a stupor and walks to the center of the room, where she recounts the story of how her husband, the pastor, disappeared during the storm years ago (“Vanished”). As she reveals her inner turmoil during the years since, she announces that her children have now gone missing. Enraged, Brom begins to run off in pursuit of Crane and the missing children but is stopped by Katrina, who reminds him that all of the tales have recurred except one: the headless groom. In the face of this evidence, Brom suggest that perhaps there’s a solution to the situation in Ichabod’s book on witchcraft, and they all crowd around to look through it. With everyone distracted by the book, Brom slips away and out of the church.

Scene 5: The Woods – Brom dashes into the clearing with his sword drawn. He calls out for Crane then softly hears muffled cries coming from the hollow tree that stands in the center of the clearing. He reaches into the opening of the tree but is immediately caught in snare that binds his wrists and lifts them high overhead, pinning him against the tree. As he calls for help, he hears the melody of the riddle being whistled as Ichabod slowly strolls into view from behind the tree. Brom demands to know what Ichabod has done with the Tenbrook children and is taunted by Ichabod as he reveals the details of how he subdued his various victims with extracts from plants and flowers. Brom tries to reason with him, but Ichabod seizes the opportunity to be done with Brom once and for all, grabs the sword, and prepares to strike, but is stopped by a bloodcurdling scream. Katrina, Faas, and the others rush in noisily trying to stop Ichabod from striking and begging for the location of the missing children. Ichabod silences them but they resume their protests. Katrina steps forward and subdues the crowd, and in an attempt to assuage him, offers herself to Ichabod, but he sees through her pretense and swings at Brom’s throat with the sword. However, Brom grips the rope, lifts his feet, and lands them squarely into Ichabod’s chest, knocking him to the ground as the sword clatters from his hands. Hans, Faas, and Zander dog-pile on Ichabod and pin him down as Katrina and Balthus rush to free Brom and Dirk picks up the fallen sword. Faas gags Ichabod with a handkerchief, and the men drag him to the tree where he is bound in the same snare that held Brom. Dirk hands the sword to Brom, encouraging him to do what Ichabod was about to do to him. Brom relents, stating that the shedding of blood, innocent or otherwise, is not the solution. As they ponder what to do with Ichabod, Sabine steps forward and decries everyone for not taking the step that could finally break the curse: offering a head to the Horseman. She picks up the sword and prepares to decapitate Ichabod. The villagers, starting with Gusta, offer themselves to be the sacrifice for the Horseman (“Make It Mine”). She is followed by Balthus, Katrina, Brom, Faas, and Rosalie, the Von Rippers, and finally Zander. As their voices rise in crescendo, Sabine takes one final swing and stops short of striking at Ichabod’s throat. Out of the breathless silence, Sabine speaks and gradually begins to reveal the story of how she had been treated all of her life by the citizens of Sleepy Hollow (“The Final Tale”). Soon, the townsfolk realize that Sabine is actually Sabilla, the witch who had beheaded her twin sister’s groom, Diedrich Knickerbocker. She had taken on her sister’s identity after the incident and lived among them all those years, waiting for a chance to pay them back. However, with their offers of sacrifice she has had a change of heart and a change of purpose and announces that she has finally found a man to replace Diedrich— a man whose heart is as dark as hers: Ichabod. After revealing that through her witchcraft she had transformed the schoolmaster and her sister into the Horseman and his horse, she cuts Ichabod loose and envelops him with her cape. There is a burst of smoke and flame, and when Brom pulls her cape away, both she and Ichabod have vanished. Immediately, the cries of the Tenbrook children are heard, the bridge reappears, and they come running across. As they are reunited with Gusta, they recount how Ichabod had given them something that made them sleepy and carried them across the bridge.

With the curse lifted and the bridge permanently restored, the villagers consider what the future holds for them (“Finale”). The Von Rippers decide to leave and make a new life for themselves. Rosalie and Faas, eager to find romantic options, prepare to leave, encouraging Katrina and Brom to join them. However, the newlyweds determine that they will be perfectly content to stay in Sleepy Hollow and make new memories. After heartfelt good-byes, the Brinkerhoffs and Van Rippers depart. Brom and Katrina dash off to enjoy their life as husband and wife, and Balthus and Zander dutifully return to the Van Tassel estate. Left alone, the Tenbrooks decide to stay, knowing that they now have all the time in the world to learn and grow and, when the time is right, travel beyond the Hollow.



Ichabod Crane – 36. The new schoolmaster of Sleepy Hollow.

Abraham “Brom” Van Bron – 22. Carpenter; secretly betrothed to Katrina.

Faas Brinkerhoff – 22. Rosalie's brother; cobbler; best friend to Brom.

Rosalie Brinkerhoff – 19. Faas's sister; best friend to Katrina.

Zander Degroot – 25. Laborer on Van Tassel's estate.

Bastian Onderdonk – 36. The former schoolmaster of Sleepy Hollow.

Balthus Van Tassel – 48. Katrina's father; landowner; widower.

Katrina Van Tassel – 20. Balthus's daughter; secretly betrothed to Brom.

Hans Van Ripper – 36. Blacksmith/stable owner; husband to Arabella.

Arabella Van Ripper – 33. Wife of Hans; mother of Mina and Dirk.

Dirk Van Ripper – 16. Son of Hans and Arabella.

Mina Van Ripper – 15. Daughter of Hans and Arabella.

Sabine Vedder – 39. Educated spinster.

Gusta Tenbrook – 38. Widow; seamstress; mother of Dorine, Willem, and Anika.

Dorine Tenbrook – 15. Daughter of Gusta.

Willem Tenbrook – 13. Son of Gusta.

Anika Tenbrook – 10. Daughter of Gusta.

Gunpowder – Ichabod's bedraggled horse.

Daredevil – Brom's horse.

Daemon – The Horseman's Horse.

The Headless Horseman

Setting: 1820; the environs of Sleepy Hollow in Upstate New York.

  1. Prologue
  2. To the Village Green
  3. A Lovely Afternoon
  4. All That We’ve Longed For
  5. Drifting Shoes
  6. To the Schoolhouse
  7. Never Spare the Rod
  8. Heads or Tails
  9. Poltergeists
  10. Choir Warm-Up
  11. This Season of Abundance
  12. Fancies
  13. A Conundrum
  14. The Letter
  15. The Best Man
  16. To the Van Tassel Estate
  17. The Proposal
  18. Beyond the Hollow
  19. Beyond the Hollow Playoff
  20. Ichabod Redux
  21. Ichabod Redux Playoff
  22. Halloween Dance
  23. Upon…
  24. The Realization
  25. Enough
  26. Alone
  27. The Midnight Chase
  28. Entr’acte
  29. This is the Day
  30. Your Heart with Mine
  31. Wedding Dance
  32. Rosalie
  33. The Wedding Feast
  34. Scarecrow
  35. Zander's Lament
  36. Smoke
  37. Fire!
  38. Unraveling
  39. To the Church
  40. Vanished
  41. Into the Night
  42. Make It Mine
  43. The Final Tale
  44. Finale
  45. Bows
  46. Exit Music

Billing responsibilities, pertinent copyright information, and playwrights' biographies are available in the show rider that comes with your license agreement. To download the show rider for Sleepy Hollow click here.

Materials: 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.

Required production materials for Sleepy Hollow: The New Musical:

  • Cast Scripts
  • Vocal Books
  • Director's Script
  • Stage Manager's Script
  • Orchestrations
  • Piano/Vocal Score


  • Piano
  • Keyboard
  • Bass
  • Drums
  • Percussion (Orchestra Bells, Xylophone, Timpani, Tubular Chimes, Pitched Woodblocks)
  • Violin 1
  • Violin 2
  • Cello
  • Reed 1 (Flute & Clarinet)
  • Reed 2 (Oboe & Clarinet)
  • Reed 3 Bassoon & Clarinet)
  • Trumpet 1 & 2
  • Trombone
  • French Horn