The Colonial Players stage a comedy adaptation of Sleepy Hollow

Washington Irving’s tale of romantic rivalry and spectral terror has spooked readers since 1820, but a new staging in Annapolis strips away schoolroom monotony for something far more whimsical and eerie. The iconic specter is haunting the streets of Annapolis this fall, bringing Halloween thrills to local audiences through a playful rendition directed by Alex Brady.

The Colonial Players Stage a Playful Adaptation

Running through November 8, 2026, at The Colonial Players of Annapolis located at 108 East Street, the production transforms the classic ghost story into a well-paced comedy. The colonialplayers.org site notes that this adaptation by John Heimbuch and Jon Ferguson blends laughs and legends for a spirited night at the theatre, evoking the cherished form of the campfire ghost story. The plot follows the awkward schoolmaster Ichabod Crane, whose appetite for fine pastries is matched only by his desire to marry Katrina Van Tassel. Standing in his way is the town prankster, Brom Bones, setting up a clash of romantic ambition and local superstition.

Nicholas Martinez brings a scholarly and conceited air to Ichabod Crane, balancing fussy arrogance with genuine vulnerability. Jack DuPree plays Brom Bones with a roaring energy and swagger, serving as the physical antithesis of his rival. Nerrie Navarro shines as Katrina Van Tassel, embodying a no-nonsense disposition and later showcasing her vocal talent as an a cappella soloist in the show’s finale.

The Colonial Players stage a comedy adaptation of Sleepy Hollow — Photo: dctheaterarts.org

Atmospheric Design and Puppetry Bring Sleepy Hollow to Life

The production relies heavily on meticulous design elements to build its eerie world. Alysia D. P. Malmstrom’s costume design captures late 18th-century Dutch apparel with tri-cornered hats and ornate jackets before shifting into imaginative supernatural attire. Scott Nichols’ minimalist set design allows Dudley Whitney’s shadow-drenched lighting to paint the spooky woods of Sleepy Hollow.

Sound design by Richard Atha-Nicholls enhances the tension with the clopping of horse hooves traveling through the theater. Meanwhile, Amy Atha-Nicholls fabricated ingenious horse puppets to represent Ichabod’s borrowed mare, Gunpowder, and the Headless Horseman’s mount. Steve Campbell brings the frightening specter to life in a mesmerizing characterization, maneuvering the cumbersome puppet and costume with ease.

The Legend of Sleepy Hollow marquee — Photo: thecolonialplayers.org

Production Details and Advisory

The performance runs approximately one hour and 25 minutes with no intermission. The Colonial Players advise audiences that the show features spooky themes, comedic scares, stylized violence, suspenseful moments, and mild language. Performances take place Thursday through Sunday evenings.