The Headless Horseman Rides into the Ozarks: A Legendary Tale at Shepherd of the Hills

Branson, MO (July 20, 2026) – A haunting legend is making its way to the Ozarks. The Shepherd of 
the Hills is pleased 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 adventure.

Set against the hillside hollow of the iconic 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, allowing nature and art to blend. 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 – The Headless Horseman Rides Again, will appear on stage this fall starting September 16th
with the final performance occurring on October 31st, Halloween Night. Times are 7:00 p.m. Wednesday
& Friday and 8:30 p.m. on Saturday.

Sleepy Hollow can be bundled with daytime fun of Shepherd’s PumpkinFest, (featuring more than 30 
fall activities and festive attractions) and then keep the fun going right into the evening with the show or
Pumpkins Aglow, a truly immersive experience. A special discount for this bundle is available at
www.shepherd.fun and any item of the package can be used whenever convenient for the guest. 
Pumpkins Aglow allows visitors to explore the family friendly magic of an enchanting nighttime walk, 
filled with illuminated pumpkins, whimsical displays, and softly lit trails that transform the Ozark hills into 
a glowing wonderland. 

Tickets are available now at www.shepherd.fun 

About Shepherd of the Hills

Shepherd of the Hills is one of the Ozarks’ most iconic landmarks, rooted in the legendary novel The 
Shepherd of the Hills written by Harold Bell Wright. First published in 1907, the novel brought national 
attention to the Ozarks and is widely credited with sparking the tourism boom that would eventually 
shape Branson, Missouri. Today, the 160-acre Shepherd of the Hills property hosts a gated attraction 
that honors its rich hospitality and storytelling heritage, offers a variety of live family entertainment, most 
notably the Outdoor Drama, which has been captivating audiences for over 65 years. Along with 
Shepherd’s Adventure Park featuring a wide variety of thrilling rides, activities, and adventures, guests 
can also enjoy seasonal events, live dinner theater, a restaurant, a coffee and ice cream shop, and 
themed shopping. Learn more at www.shepherd.fu