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The Headless Horseman Files
Immerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane.
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!
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.
Recommended for ages 8+. Timed admission to this 45 minuted guided experience.
2025 dates: October 3 – November 1. Fridays-Sundays plus Columbus Day.
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There’s something for everyone in Sleepy Hollow Country—farmers markets, live music, street fairs, historic homes, hiking trails, kayaking and boating on the Hudson River. Halloween season brings even more for the whole family—haunted hayrides, blazing pumpkins, costumed 10K run, Halloween parade, and of course, the Headless Horseman! For the latest on Fall events, visit our guide to Halloween in Sleepy Hollow.