Photos: SLEEPY HOLLOW THE MUSICAL At The Players Theatre 

Be Bold! Productions Sleepy Hollow the Musical continues its run Off-Broadway at the Players Theatre after previews this past weekend. The musical runs through Sunday, Nov 9. Check out photos of the production.

Wayfaring schoolmaster Ichabod Crane (Jack Wooton) becomes lost as he travels through the Sleepy Hollow woods on his way to take up his new teaching position in the town. He is discovered by his landlord Hans Van Ripper (Eric Fletcher), who leads him to the safety of the town, away from the spooky spirits that haunt the Hollow (Avery Ilardi, Tess Majewski, Emily Thamm-Avsyuk, Magen Willis). 

With the town abuzz about their new arrival, Lady Van Tassel (Sue-Ellen Mandell) is excited about what this new prospect might mean for her daughter Katrina (Lauren Updyke) and her future. However, unlike her friend Anna (Shea Coughlin-Jacobs), Katrina isn’t interested in Ichabod as a beau – she has her eye on her long-time love interest Brom Bones (Gabe DeRose).  

Brom’s reticence on the matter of commitment and romance, and his too foolish antics with his friends Henry (Will Ernest Adams), George (Wesley Gardner), and John (Max Hunkler) leads Katrina to hatch a plan to make him jealous by flirting with Ichabod. She sings of her determination to win Brom no matter what with Anna and their friend Sarah (Nicole Gardner). 

With many interwoven relationships and the specter of the Headless Horseman (Max Hunkler) hanging over the town, the inhabitants must turn to their inner fortitude for survival – both in love and life.  

The creative team of Sleepy Hollow the Musical are Brenda Bell (Playwright/Director), Michael Sgouros (Musical Director and Composer), Shino Frances (Choreographer) Courtney Hansen (Costumes), Elizabeth Chaney (Set Design), Emma Ruopp (Production Manager), Jessica Choi (Lighting Designer), Kelley Alogna (Production Manager), Matthew Davis (Assistant Stage Manager), and Violence Director (Luke Pearlberg). Marketing team members are Charlene Ilardi (Group Sales) and Andrea Woodbridge and Tracey Yakkey. 

Will you survive what lurks in the Hollow? Find out by joining us for Sleepy Hollow the Musical now through Nov 9, 2025, Fridays and Saturdays at 7p / Saturdays at 3p / Sundays at 2p Off-Broadway at The Players Theatre, located at 115 MacDougal St. The theatre is accessible via West 4th St. Station, lines A,C,E,B,D,F,M – walk one block east on West 3rd, and one block south on MacDougal. 

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