A classic tale about a man who took a very long nap—and the strange things that happened as he slept. Based on a story by Washington Irving
Learning Objective: Students will identify and analyze the setting of a play based on the story of Rip Van Winkle.
Peter Vanderdonk: The tale you are about to hear is not one you will find in history books.
Katrina Knickerbocker: But that doesn’t mean it didn’t happen.
Peter: History is more than facts. History is also stories.
Katrina: Like the story of Rip Van Winkle.
Odd Fellows (whispering): Rip Van Winkle . . .
Peter: And the Odd Fellows who lured him away.
Odd Fellows (whispering): Rip Van Winkle . . .
Peter: Our story begins in 1769.
Katrina: The United States was not a country back then.
Peter: New York was one of the 13 Colonies owned by Great Britain.
Katrina: And ruled by King George III.
Peter: Soon the American Revolution would change that.
Katrina: Those are the facts indeed. But let’s get back to the story.
Scene 1
A village near the Catskill Mountains,
New York, 1769
N1: Rip Van Winkle relaxes on a bench with a few friends and his dog, Wolf.
N2: They’re in front of the Village Inn, a small hotel and restaurant. A painting of King George III hangs above the door.
Nicholas Vedder: Business at the inn has been slow.
Derrick Van Bummel: No wonder! Who can afford to visit?
Brom Dutcher (angrily): Everything is more expensive thanks to King George’s taxes!
Nicholas (worried): Hush! If a British soldier hears you, you could get in trouble for criticizing the king.
N3: Just then, Rip’s wife, Cornelia, arrives. Their daughter, Judith, is behind her.
Brom: Uh-oh.
Cornelia: Rip Van Winkle, if you’re not off flying a kite, you’re here doing nothing!
N1: Rip shrugs. Wolf lies down with a sigh.
Cornelia: I asked you to milk the cow, feed the chickens, and look after our daughter. I come home to find the cow un-milked, the chickens un-fed, and little Judith running around, screeching like an angry cat!
Rip: I was busy.
Cornelia: Busy?
N2: Rip gazes down helplessly.
Cornelia (sighing): I’m going home.
N3: Cornelia storms off with Judith.
Rip: Wolf, I think tomorrow would be a fine day to go hunting in the mountains.
Wolf (thumping his tail): Woof!
Scene 2
Catskill Mountains, the next evening
N1: Towering mountains rise above the Hudson River.
N2: The setting sun glows orange through the forest.
N3: Rip rests against a tree. Wolf lies in the grass nearby.
Rip: It’s beautiful up here, isn’t it, Wolf?
Wolf: Woof!
Odd Fellows (from afar): Rip Van Winkle . . .
Rip (looking around): Did you hear that, Wolf?
Wolf: Aarh?
Odd Fellows (growing closer): Rip Van Winkle!
N1: Rip’s shoulders tense. Wolf sits up straight.
N2: A short, bearded man appears—one of the Odd Fellows. He is dressed like the Dutch explorers who came to the Catskill Mountains some 150 years earlier.
N3: The Odd Fellow carries a wooden barrel on one shoulder. He motions for Rip to help.
Rip: Where are you headed?
N1: The Odd Fellow points up the mountain.
Rip (nervously): All right. Here, let me carry that.
N2: Rip takes the barrel and starts following the Odd Fellow.
N3: Wolf hurries along, his tail tucked between his legs.
Art by Carolyn Ridsdale
Scene 3
Higher in the Catskill Mountains,
a short while later
N1: The Odd Fellow, Rip, and Wolf hike up a rocky mountain path.
Rip (out of breath): So, what’s your name?
N2: The Odd Fellow does not respond.
Rip: What’s in the barrel, by the way? I hear a liquid sloshing inside.
N3: Still the Odd Fellow says nothing.
N1: Suddenly, Rip, Wolf, and the Odd Fellow reach a clearing in the forest.
N2: More Odd Fellows are playing ninepins, a game similar to bowling.
N3: No one speaks. The only sound comes from the game balls, which rumble like thunder as they roll.
N1: One Odd Fellow pours the contents of the barrel into cups. He gestures for Rip to serve them.
Rip (hands shaking): Here you go, gentlemen.
N2: The men drink silently and return to their game.
Rip (to himself): What are these men drinking? I’m sure it wouldn’t hurt to have a sip.
N3: He drinks.
Rip: Delicious!
N1: Rip takes another sip. Then another.
N2: Little does he know . . .
N3: . . . it’s a magic potion.
N1: He sits down and falls into a deep sleep.
Scene 4
Under a tree, a bright morning
N2: Rip is still asleep. He tosses and turns, then opens his eyes.
Rip: Did I sleep here all night? What will I tell Cornelia?!
N3: Rip looks down to see his beard has grown many feet long and is all white.
Rip (confused): What happened to my beard? And where is Wolf?
N1: Rip calls out, beginning to panic.
Rip: Wolf! Wolf! Here, boy!
N2: Wolf does not appear.
Rip: Did those fellows take my dog?
N3: Rip stands up, clutching his aching back.
Rip: Ouch! My back wasn’t this sore when I fell asleep.
N1: Rip looks around the clearing.
Rip: I must find those fellows and end this joke.
Art by Carolyn Ridsdale
Scene 5
The village near the Catskill Mountains, later that morning
N2: Rip rushes back to the Village Inn. He notices its sign has changed. Now it reads “The Union Hotel.”
N3: The painting of King George III is gone too. The portrait of another man hangs in its place.
N1: Rip has a bewildered look on his face.
N2: Two children come up to him.
Rip: Who is the man in that portrait?
Willem (confused): It’s President George Washington of course! Why are you wearing those old clothes, sir?
Rip: Old clothes? You’re the ones who are dressed oddly.
Helen: No, you are!
Rip: Have I gone mad?
N3: A crowd gathers around.
Theo: Who are you? Have you lost your way?
N1: Rip grows nervous from all the attention.
Rip: I . . . I’m a quiet man . . . and I’m loyal to the king.
Crowd: Gasp!
John: He’s a spy for the British!
Rip: I mean no harm!
John: What are you doing here? Tell us, before we throw you in jail!
Rip (nervously): I fell asleep in the mountains. Some fellows in old fashioned clothes stole my dog. Then they . . . disappeared.
N2: The villagers look at Rip with suspicion.
Rip: I came back here, but everything is different. I just want to find my friends!
Theo: Who are they?
Rip: Nicholas Vedder? Brom Dutcher? Derrick Van Bummel?
N3: An old woman speaks up.
Katrina: Nicholas died 18 years ago. Brom went off to war and never came
back. Derrick works as a politician in the U.S. government.
Rip: Wh . . . what?
N1: Shocked, Rip faints.
Scene 6
The Union Hotel, moments later
N2: Rip awakens, surrounded by people.
John: Listen, old man, what is your name?
Rip: I . . . I’m not sure.
N3: A woman in the crowd is holding a crying baby.
Judith (to the baby): Hush, little Rip.
Rip: What is your name, good woman?
Judith: Judith.
Rip: And your father?
Judith: Rip Van Winkle. But no one has heard from him in 20 years. His poor dog came home without him.
Rip (shaking): And . . . your mother?
Judith: Cornelia. She died long ago.
N1: Rip’s eyes widen.
Rip: Judith, it’s me, your father! That baby must be my grandson. Don’t you recognize me?
Judith: I was a child when my father left.
N2: Katrina studies Rip’s face.
Katrina: Why, it is Rip Van Winkle! Where have you been all these years?
Rip: To me, it’s been only one night.
John: What nonsense.
Peter (quietly): I believe him.
Crowd: You do?
Peter: I do. The Catskill Mountains have always been haunted by strange beings.
N3: Thunder roars in the distance.
Peter: My own father once saw ghosts of the old Dutch explorers, bowling on the mountain. He said their game sounded like thunder.
Rip: Yes! Exactly!
Judith (amazed): So you are my father! You shall live with me, my husband, and baby Rip.
Epilogue
Katrina: It took time for old Rip to grasp all that had happened while he slept.
Peter: We had a revolution.
Theo: We freed ourselves from King George.
John: We formed a new country, the United States of America.
Willem: Now Rip once again relaxes on the bench by the inn . . .
Helen: . . . and tells his story to anyone who will listen.
John: Some think he is crazy.
Theo: But others believe him.
Judith: And whenever we hear thunder, we say the Dutch must be playing their game of ninepins again.
Think & Write
Imagine you have an old uncle Rip who fell asleep 20 years ago and just woke up. What changes would most surprise him? Include at least three in a paragraph.
This article was originally published in the March/April 2026 issue.
