The Headless Horseman Files at Philipsburg Manor
*The event has already taken place on this date: Sat, 11/01/2025
An Immersive Sleepy Hollow Whodunit! BRAND NEW THIS YEAR! Follow your guide on a mysterious 45-minute walk through the historic grounds of Sleepy Hollow’s Philipsburg Manor, where you’ll step into a chilling, live-action 18th-century whodunit. Along the way, encounter suspicious townsfolk like fiery Hans Van Ripper, charming Katrina Van Tassel, spectral Hulda the Witch, and bold Brom Bones—each with their own tale and motive for causing the demise of Ichabod Crane. What is that lurking in the shadows? The Headless Horseman himself!
Please help us keep this calendar up to date! If this activity is sold out, canceled, or otherwise needs alteration, email mindy@kidsoutandabout.com so we can update it immediately. If you have a question about the activity itself, please contact the organization administrator listed below.
This is no ordinary walking tour—it’s an interactive theatrical journey, perfect for all ages, where you and your group must piece together clues, uncover hidden truths, and decide for yourselves what really happened to Ichabod Crane.
STRONGLY RECOMMENDED FOR AGES 8+ ONLY!
Please note that while the event is largely playful and tongue-in-cheek, it has the following elements:
Darkness: One portion of the experience takes place in low light or near darkness, which may be disorienting or a little frightening for younger children.
Eerie themes: The experience includes light suspense, eerie moments, and references to the supernatural and death, which may not be suitable for very young audiences.
Additional warnings: One scene involves transitions from bright outdoor settings to low-light interiors. These shifts may be uncomfortable for individuals with light sensitivity or photosensitivity.
*Times, dates, and prices of any activity posted to our calendars are subject to change. Please be sure to click through directly to the organization’s website to verify.
Location:
Philipsburg Manor381 North Broadway
Sleepy Hollow, NY, 10591United States
See map: Google Maps
Phone:
914-366-6900Contact name:
Historic Hudson Valley
Email address:
The event has already taken place on this date:
11/01/2025
Time:
See website
Ages
6-8 years 9-12 years Teenagers Adults & kids together Adults without kidsWeb Service