The Legend of Sleepy Hollow

The Colonial Players of Annapolis presents *The Legend of Sleepy Hollow*, a theatrical adaptation by John Heimbuch and Jon Ferguson of Washington Irving’s classic ghost story. In the superstitious village of Sleepy Hollow, nervous schoolteacher Ichabod Crane pursues Katrina Van Tassel while contending with romantic rivals, village gossip, and the possibly real—and deeply frightening—Headless Horseman. The production combines comedy, folklore, suspense, and stylized theatrical scares.

Director Alex Brady approaches the story as a campfire ghost tale, evoking autumn leaves, wood smoke, fading daylight, and the uneasy feeling that something supernatural may be just beyond view. Rather than relying on film-style jump scares, gore, or haunted-house tricks, the production uses atmosphere, interpersonal tension, surprise, theatrical imagery, and humor to make fear entertaining while preserving the story’s sense of wonder.

When: October 23 through November 8, 2026.

Showtimes: Friday, October 23 at 8:00 PM; Saturday, October 24 at 8:00 PM; Sunday, October 25 at 2:00 PM; Thursday, October 29 at 8:00 PM; Friday, October 30 at 8:00 PM; Saturday, October 31 at 8:00 PM; Sunday, November 1 at 2:00 PM; Thursday, November 5 at 8:00 PM; Friday, November 6 at 8:00 PM; Saturday, November 7 at 8:00 PM; and Sunday, November 8 at 2:00 PM. The October 23 performance is the opening, and the November 8 performance is the closing matinee.

Run time: Approximately 1 hour and 20 minutes.

Format: The production is staged in the round.

Ages and content: The show contains spooky themes, comedic scares, suspenseful moments, stylized violence, and mild language. The page does not provide a specific recommended age.

Tickets: Price not available.

Venue: Colonial Players of Annapolis.

Playwrights: John Heimbuch and Jon Ferguson.

Director: Alex Brady, who has previously directed *Ravenscroft* and *The White Rose* for The Colonial Players. He has also performed as Macbeth with The Theatre @AACC and has more than 20 years of experience as a lighting designer in professional, academic, and community theaters throughout Maryland, Northern Virginia, and Washington, D.C. He has received multiple award nominations for his lighting work, served as resident lighting designer for the AACC Dance Company, and volunteered as a designer and technical adviser for local high schools. Brady is a certified audiovisual engineer, teaches film and architectural history as an adjunct faculty member at Anne Arundel Community College, hosts the *Grim Scenarios* podcast and livestream, and is an alumnus of St. John’s College. He previously served on The Colonial Players’ board as Education Director.

Cast: Nicholas Martinez plays Ichabod Crane. Abby Wilson plays Geoffrey Crayon and returns to The Colonial Players after appearing as Beatrice in *Poor Clare*. Jack DuPree plays Brom Bones. Nerrie Navarro makes her Colonial Players of Annapolis debut as Katrina Van Tassel. Matt Leyendecker plays Baltus Van Tassel and has a personal connection to the Sleepy Hollow area, including Tarrytown, New York, where his father was born and raised. Jadiah Reubel plays Hans Van Ripper in his theatrical debut. Alex Miletich IV plays Parson Van Houten. Carrie Gross plays Rupert Van Brunt and returns to the stage after extensive work in costume, set design, and technical theater. Amanda Matousek plays the Storyteller. Steve Campbell makes his Colonial Players debut as the Headless Horseman. Amanda Connelley plays the Skeleton along with several ensemble roles, including Villager 1, Country Girl, Student 5, and Woman in White.

Production team: Nathan Garcia is the assistant director and stage manager, with Camille Jones as assistant stage manager. George W. King III is the producer. Dex Breneman is on the stage crew. Scott Nichols is set designer and play consultant, with Leo Lin Kubit and Lexington Graham as set painters. Carrie Shade and Autumn Embry are properties designers. Dudley Whitney designed the lighting and special effects. Richard Atha-Nicholls designed the sound, and Alysia Malmström designed the costumes with assistance from Christina McAlpine and Autumn Embry. Cadence Wrotny and Will Simpson are costume apprentices, and Malmström and Embry are dressers. Felicity Alexandra designed hair and makeup, while Amanda Matousek is the movement coordinator. Amy Atha-Nicholls created the horse puppets and poster. Ken Kaiser, Pete McDevitt, Bob Mumper, Todd Breese, Edd Miller, and Tom Cosgrove are carpenters. Kady Robshaw, Fae Leonard, and Brad Phillips are booth technicians. Nancy Long and Elli Swink are program proofreaders.