Sleepy Hollow

The Headless Horseman rides again at Shepherd of the Hills

by The Shepherd of the Hills· Branson, MO
From$48.62
Group size12
Ages4–104

What to Expect

Dare to step into a chilling autumn legend as Sleepy Hollow comes to life in the open air at the Thurman Old Mill Outdoor Theater.

Inspired by Washington Irving’s timeless tale The Legend of Sleepy Hollow, this atmospheric outdoor production plunges you 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 the Hollow for generations—the Headless Horseman.

Set against the rustic backdrop of the historic mill, the natural sounds of the Ozarks and the glow of moonlight heighten every suspenseful moment. With dramatic lighting, haunting music, period costumes, and thrilling stage effects, this is not just a play—it’s an immersive fall experience where the legend feels uncomfortably close.

Perfect for crisp autumn evenings, Sleepy Hollow – Outdoor Play 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.

Includes

  • Does not include dinner

Duration

1.5 Hours

Address

5585 W. 76 Country Blvd, Branson, MO 65616

Pricing

Adult · Adult - Show Only ($49.95 + 6% Booking Fee)$53.62
Adult & Park Admission$64.14
Child · Ages 4-12 - Show Only ($29.95 + 6% Booking Fee)$32.15
Child & Park Admission$45.89
Family Pass for 4 + Pizza · Includes 2 Adults and 2 Children + Pizza Package$149.22
Family Pass for 5 · 2 Adults and 3 Children$123.45
Family Pass for 6 · 2 Adults and 4 Children$138.48

Prices are typical; see the booking calendar for live availability and rates.

Cancellation Policy

Please understand the 48-hour cancellation policy. No refund will be given to any cancellations within 48-hours of the showtime.

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