Sleepy Hollow: The Lost Chapter

by Jeremy Sony

We all know The Legend of Sleepy Hollow. Or do we? After Ichabod Crane was chased down by the Headless Horseman and vanished into the night, a new schoolteacher, Abigail Seymour, moves to town. She's more concerned with teaching than listening to ghost stories, but soon discovers that the Headless Horseman is still out there. And worse? He's after her! Now, Abigail and her students must hurry to retrace Ichabod...

We all know The Legend of Sleepy Hollow. Or do we? After Ichabod Crane was chased down by the Headless Horseman and vanished into the night, a new schoolteacher, Abigail Seymour, moves to town. She's more concerned with teaching than listening to ghost stories, but soon discovers that the Headless Horseman is still out there. And worse? He's after her! Now, Abigail and her students must hurry to retrace Ichabod's final days in Sleepy Hollow and find a way to stop the Horseman once and for all, lest she meet the same fate. As they race to solve the mystery of what really happened, Abigail crosses paths with Katrina Van Tassel, Brom Bones, and all of Irving's original characters — uncovering secrets and revelations about that fateful night in Sleepy Hollow. This full-length stage play picks up in the final pages of Washington Irving's classic, revealing a previously untold piece of the legend.

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Sleepy Hollow: The Lost Chapter

Character Information

Diverse casting is encouraged. The play lives in 1790; we do not. The play is designed to work with 15 actors, solely for economy, doubling as follows: (Josephine Koning / Diedre Van Hart), (Margriet Gelderland / Eleanor Van Tassel), (Hans Van Ripper / Baltus Van Tassel / Horseman). If you want to cast each part individually, you can.
  • Katrina Van Tassel
    Kind, wealthy, engaged to Brom.
    Can be played by:
    • Actor Age
      20s,
      30s
    • Actor Gender Identity
      Woman
  • Headless Horseman
    Usually doubled by actor playing Hans / Baltus; no lines
    Can be played by:
    • Actor Age
      20s,
      30s,
      40s,
      50s,
      60s,
      70s+
  • Baltus Van Tassel
    Katrina's father
    Can be played by:
    • Actor Age
      50s,
      60s,
      70s+
    • Actor Gender Identity
      Man
  • Hans van Ripper
    Stuck in his ways.
    Can be played by:
    • Actor Age
      50s,
      60s,
      70s+
    • Actor Gender Identity
      Man
  • Eleanor van Tassel
    Katrina's mother
    Can be played by:
    • Actor Age
      40s,
      50s
    • Actor Gender Identity
      Woman
  • Margriet Gelderland
    Revolutionary War widow
    Can be played by:
    • Actor Age
      40s,
      50s,
      60s,
      70s+
    • Actor Gender Identity
      Woman
  • Diedre van Hart
    Revolutionary War widow
    Can be played by:
    • Actor Age
      40s,
      50s,
      60s,
      70s+
    • Actor Gender Identity
      Woman
  • Josephine Konig
    Former inn keeper. Susanna's mother.
    Can be played by:
    • Actor Age
      50s,
      60s,
      70s+
    • Actor Gender Identity
      Woman
  • Ichabod Crane
    Thinks he's the smartest person in the room.
    Can be played by:
    • Actor Age
      20s,
      30s,
      40s
    • Actor Gender Identity
      Man
  • Brom Van Brunt
    "Brom Bones" - a jovial braggart. Engaged to Katrina.
    Can be played by:
    • Actor Age
      20s,
      30s
    • Actor Gender Identity
      Man
  • Abigail Seymour
    Sleepy Hollow's newest schoolteacher; progressive for her time
    Can be played by:
    • Actor Age
      20s,
      30s
    • Actor Gender Identity
      Woman
  • Sarah van Brunt
    Brom's sister, works at the Inn.
    Can be played by:
    • Actor Age
      20s,
      30s
    • Actor Gender Identity
      Woman
  • Susanna Koning
    The Innkeeper. A gossip. Superstitious.
    Can be played by:
    • Actor Age
      20s,
      30s,
      40s,
      50s
    • Actor Gender Identity
      Woman
  • Peter
    Future troublemaker and loyal.
    Can be played by:
    • Actor Age
      Child
    • Actor Gender Identity
      Man
  • Rose
    The youngest. Good-natured and cautious.
    Can be played by:
    • Actor Age
      Child
    • Actor Gender Identity
      Woman
  • Catherine
    Hanna's best friend. Sweet and protective.
    Can be played by:
    • Actor Age
      Teens
    • Actor Gender Identity
      Woman
  • Nathaniel
    Kind and unassuming, he believes in ghosts.
    Can be played by:
    • Actor Age
      Child,
      Teens
    • Actor Gender Identity
      Man
  • Samantha
    The class brain. Prudent and logical.
    Can be played by:
    • Actor Age
      Child,
      Teens
    • Actor Gender Identity
      Woman
  • Hanna
    Brave and headstrong; eldest and self-appointed leader of the students.
    Can be played by:
    • Actor Age
      Teens
    • Actor Gender Identity
      Woman

Development History

  • Reading, Curtain Players Theatre, 2013
  • Commission, ClassAct Dramatics at Street Theatre Co., 2013

Production History

  • Community Theater, Curtain Players Theatre, 2019
  • High School, ClassAct Dramatics at Street Theatre Co., 2013