The Legend(s) of Sleepy Hollow

You know one version, the popular version, of Washington Irving’s tale of the Headless Horseman of Sleepy Hollow— but wouldn’t you like to know what really happened on that fateful night that Ichabod encountered the Horseman? This play reveals all from the point-of-view of the one character who was there and knows the whole truth: Ichabod Crane’s horse, Gunpowder.

Adapted from Washington Irving's "The Legend of Sleepy Hollow"


Run Time: 65 min

Cast Size: 3F, 3M (Flexible)

Themes: Supernatural, Romance, Puritanism, Natural World, American Folklore


From the play:

Did you like that little story? The “legend” of Sleepy Hollow— as it were? Ichabod, Katrina and all that— the Horseman, pretty good? Yeah? Fun story? Hmmmmm? Well that’s NOT how it happened.



Plot / Synopsis





Storytellers 1-4 (F/M) – The voices and setting of Sleepy Hollow (roles can be divided in half).

Ichabod Crane (M) – A Connecticut Schoolmaster— very friendly, huge appetite.

Katrina Van Tassel (F) – A fair damsel, a bit of a coquette.

Baltus Van Tassel (M) – Katrina’s father, a wealthy farmer.

Brom Bones (M) – The self-proclaimed hero of the country round.

School Boy (F/M) – A jerky kid with a secret.

Servant (F/M) – A wise and loyal bodyguard.

Messenger (F/M) – A cranky deliverer of news.

Headless Horseman (F/M) – The terrifying spectre of Sleepy Hollow.

Gunpowder (F/M) – Ichabod’s loyal and energetic horse.

Suggested actor doubling for 6 actors:

  • Storyteller 1/Katrina Van Tassel
  • Storyteller 2/Baltrus Van Tassel
  • Storyteller 3/Brom Bones
  • Storyteller 4/School Boy/Servant/Messenger
  • Ichabod Crane
  • Gunpowder


Minimum cast: 6 – 1 F, 3 M, 2 F/M
Maximum cast: 17 - 1 F, 3 M, 13 F/M (additional actors can be used as townspeople, school children, and the world of Sleepy Hollow— trees, scary things in the forest, etc.)

Setting:The play takes place in numerous settings throughout early 19th century Upstate New York. The settings include a school house, the Van Tassel Mansion, several country roads, a glen, and the route where Ichabod is chased by the Headless Horseman.


Production Costs