The Colonial Players stage The Legend of Sleepy Hollow in Annapolis
Washington Irving’s 1820 tale of romantic rivalry and spectral terror comes to Annapolis as The Colonial Players stage a fresh, comedic adaptation of The Legend of Sleepy Hollow through November 8, 2026, mdtheatreguide.com reported.
Classic American Spooks on the Annapolis Stage
Set in the Dutch hamlet of Sleepy Hollow in 1801, the production follows the awkward and pompous schoolmaster Ichabod Crane. His desire to marry Katrina Van Tassel runs headlong into opposition from the town’s boisterous prankster, Abraham Van Brunt, also known as Brom Bones. As autumn deepens, Ichabod grows increasingly spooked by local superstitions before his fears culminate in a fateful midnight encounter with the Headless Horseman.
Nicholas Martinez stars as the gawky outsider Ichabod Crane, balancing fussy arrogance with genuine vulnerability. Jack DuPree plays Brom Bones with a confident, roaring energy and physicality, while Nerrie Navarro appears as the bright and slightly intimidating Katrina Van Tassel.
Cast Members Bring Washington Irving Characters to Life
Amanda L. Matousek opens the play as the principal narrator, the Storyteller, while Abby Wilson plays Geoffrey Crayon, Washington Irving’s literary alter ego injected into the production as a townsperson. Jadiah Reubel makes his stage debut as Hans Van Ripper, alongside Alex Miletich IV as Parson Van Houten and Matt Leyendecker as Baltus Van Tassel. Carrie Gross rounds out the cast as little Rupert Van Brunt, while Steve Campbell and Amanda Connelley portray townspeople and phantoms, with Campbell taking on the role of the Headless Horseman.
Costume designer Alysia D. P. Malmstrom outfitted the cast in late 18th-century Dutch apparel that transitions into ethereal supernatural elements. Set designer Scott Nichols and lighting designer Dudley Whitney utilized minimalist structures alongside shadow-drenched lighting to evoke the woods of Sleepy Hollow. Puppets engineered by Amy Atha-Nicholls bring midnight-black steeds and borrowed mares to life on stage, supported by sound design from Richard Atha-Nicholls and properties designed by Carrie Shade and Autumn Embry.
Performances at The Colonial Players
The production runs for approximately one hour and 25 minutes with no intermission. Performances take place Thursdays through Sundays at The Colonial Players of Annapolis, located at 108 East Street in Annapolis, Maryland.
The venue advises audiences that the show features spooky themes, comedic scares, stylized violence, suspenseful moments, and mild language. Tickets and additional information remain available online through the theater’s box office.