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. 

Perfect for families, couples, and groups looking for an unforgettable night of entertainment, Sleepy Hollow will run on select evenings in the fall season. Guests can spend the day enjoying PumpkinFest, featuring more than 30 fall activities, festive attractions, and family-friendly fun throughout the park. As evening arrives, visitors can wander through the glowing magic of Pumpkins Aglow, an enchanting nighttime walk, filled with illuminated pumpkins, whimsical displays, and softly lit trails that transform the Ozark hills into a glowing autumn wonderland. The evening then culminates with the thrilling outdoor production of Sleepy Hollow under the Ozark night sky.

Tickets for Sleepy Hollow are available now at www.shepherd.fun. Early booking is recommended, as seating is limited and demand is expected to be high.