Sleepy Hollow - The Headless Horseman Rides Again

A haunting legend is making its way to the Ozarks. The Shepherd of the Hills is proud to announce the arrival of Sleepy Hollow The Headless Horseman Rides Again, an all-new live production bringing the classic haunted tale of Ichabod Crane and the Headless Horseman to life in a thrilling outdoor theatrical experience.

Set against the historic hills of the Old Mill Theater, this immersive retelling of Washington Irving’s timeless story promises a captivating blend of suspense, action, humor, and heart. Audiences will step into a world of flickering lanterns, galloping hooves, and eerie encounters as the legendary Headless Horseman rides under the Ozarks night sky.

Building on a legacy of unforgettable live entertainment, The Shepherd of the Hills continues its tradition of larger-than-life storytelling with talented performers, atmospheric staging, and the natural beauty of an outdoor setting. Sleepy Hollow will feature high-energy chase scenes, authentic period costuming, and family-friendly thrills designed to keep guests on the edge of their seats.