Sleepy Hollow

Dare to step into a chilling autumn legend as Sleepy Hollow: The Headless Horseman Rides Again comes to life in the open air at the historic Thurman Old Mill Outdoor Theater. The Shepherd of the Hills proudly presents this all-new live production, bringing Washington Irving’s timeless tale of Ichabod Crane and the Headless Horseman to the Ozarks in a thrilling and immersive theatrical experience.

Set against the rustic beauty of the historic mill and surrounding hills, this atmospheric retelling plunges audiences into a world of shadowy woods, flickering lanterns, and whispered warnings. Follow the ill-fated schoolmaster Ichabod Crane as he encounters superstition, romance, and the terrifying specter that has haunted Sleepy Hollow for generations. Under the glow of moonlight and the natural sounds of the Ozarks, every moment is heightened with suspense, wonder, and just the right touch of humor and heart.

Building on a legacy of larger-than-life storytelling, this outdoor production features talented performers, dramatic lighting, haunting music, authentic period costuming, and high-energy chase scenes that bring the legend vividly to life. More than just a play, it’s a fully immersive fall experience—where galloping hooves echo through the night and the Headless Horseman may feel uncomfortably close.

Perfect for crisp autumn evenings, Sleepy Hollow blends classic storytelling with spine-tingling spectacle, making it a must-see seasonal event for families, thrill-seekers, and lovers of folklore alike.

The legend rides again… if you dare to watch.