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  • The Headless Horseman Files

    The Headless Horseman Files
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Four suspects, one missing schoolmaster, and 45 minutes to work out what happened — Sleepy Hollow's whodunit, staged in broad daylight. A guide walks you through the grounds of Philipsburg …

    $25 – $35
  • Glass Pumpkin Patch Fundraiser

    Glass Pumpkin Patch Fundraiser
    Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

    The Village of Sleepy Hollow welcomes back the artists from the Adirondack Glassblowing Studio for the 4th annual Glass Pumpkin Patch Fundraiser in Kingsland Point Park. This festive event will …

    Free
  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker Tour: Washington Irving & "The Legend of Sleepy Hollow" Meet the father of the American short story on this one-hour walking tour through the south end of …

    $20
  • Myths & Mysteries of The Octagon House

    Myths & Mysteries of The Octagon House
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    A Halloween-season guided tour at the Armour-Stiner Octagon House, Irvington, NY For generations, the eight-sided Armour-Stiner Octagon House has inspired whispered local legends, and this fall its guides are opening …

    $38
  • Sleepy Hollow Oktoberfest

    Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

    German food and beer, live Bavarian music, and the Hudson at your back — Sleepy Hollow's Oktoberfest returns for its 14th year. After being postponed due to weather, the Sleepy Hollow …

    Free – $5
  • The Sailhouse Oyster Fest

    The Sailhouse Oyster Fest
    The Sailhouse 238 Green Street, Tarrytown, NY, United States

    This October, The Sailhouse puts its own waterfront spin on the season with Oyster Fest, a series of four Sunday afternoons of fresh oysters, seasonal cocktails, and live music on …

    Free
  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker Tour: Washington Irving & "The Legend of Sleepy Hollow" Meet the father of the American short story on this one-hour walking tour through the south end of …

    $20
  • A Very Grimm Story Spooktacular with Adam Gidwitz

    The Ark at the Shames JCC 371 South Broadway, Tarrytown, NY, United States

    The fairy tales you thought you knew are about to get a Grimm makeover—live on stage! This family-friendly event brings the hit podcast Grimm, Grimmer, Grimmest to life for an …

    $30 – $50
  • Spirits of Sleepy Hollow Country

    Spirits of Sleepy Hollow Country
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Sleepy Hollow has more ghosts than the Horseman. Two illusionists intend to get them talking. Mark Clearview and Nick Wallace return to Philipsburg Manor this October with an original magic show built around the spirits …

    $65 – $89
  • The Original Knickerbocker Tour

    The Original Knickerbocker Tour
    Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United States

    The Original Knickerbocker Tour: Washington Irving & "The Legend of Sleepy Hollow" Meet the father of the American short story on this one-hour walking tour through the south end of …

    $20
  • An Audience with Poe

    An Audience with Poe
    Historic Hudson Valley 639 Bedford Road, Tarrytown, United States

    Sip, savor, and shiver with Poe’s darkest tales brought to life through storytelling, cocktails, and confections. Professional storytellers bring to life the “powerful graphic effect” that Washington Irving once praised …

    $65
  • Slapering Hol Press Presents the Debut Poets Reading

    Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States

    Join us in-person at the Hudson Valley Writers Center for an afternoon of terrific poetry from Ellen Goldsmith, Richard Parisio, Avia Tadmor, and Zoë Ryder White. Hosted by the editors …

    Free
  • Irving’s Legend at Sunnyside

    Irving’s Legend at Sunnyside
    Sunnyside 3 W Sunnyside Lane, Irvington, NY, United States

    Hear the Legend told on Washington Irving's own lawn. Washington Irving is buried a few miles up the road. Every October, his most famous story comes back to the house …

    $40 – $45
  • Twilight Village at Sleepy Hollow

    Twilight Village at Sleepy Hollow
    Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United States

    Where the Legend Lives After Dark! Mix and mingle with storytellers, fire performers, and iconic Legends. Enjoy a roving brass band, a pop-up evening market, and much more. Expanded experiences, …

    $25 – $35
  • The Great Jack O’Lantern Blaze

    The Great Jack O’Lantern Blaze
    Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United States

    More than 7,000 hand-carved jack o'lanterns light up the riverside grounds of Van Cortlandt Manor. Ten acres of an 18th-century estate above the Hudson become a half-mile walk past life-sized …

    $24 – $189
  • Whose Live Anyway?

    Tarrytown Music Hall Performances
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    The current cast members of the Emmy-nominated TV show Whose Line Is It Anyway? are proud to present their new improv tour: WHOSE LIVE ANYWAY? WHOSE LIVE ANYWAY? is 90 …

    $76 – $86
  • Sleepy Hollow Cemetery Lantern Tour

    Sleepy Hollow Cemetery Lantern Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Step back in time and explore Sleepy Hollow Cemetery by kerosene lantern light. This two-hour evening walk is the perfect introduction to why these storied grounds are so famous—an atmospheric …

    $50

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.