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  • 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 where he spent his last twenty years — performed outdoors, after dark, on the grounds of Sunnyside. Master storyteller Jonathan Kruk has been doing this …

    $40 – $45
  • The Lady in White

    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    An immersive ghost story tour at the Armour-Stiner Octagon House, Irvington, NY Some ghost stories are told about a house. This one is performed inside it. In The Lady in White, guests move through the rooms of the Octagon House as a story written by one of the home's own residents plays out around them. …

    $58
  • The Legend of Sleepy Hollow and Local Lore

    The Legend of Sleepy Hollow and Local Lore
    Rockwood Hall Phelps Way, Pleasantville, NY, United States

    Follow a lamplit path to the ruins of Rockwood Hall, high above the Hudson, where storyteller and author David Neilsen is waiting with an evening of Sleepy Hollow's lesser-known ghost stories — and one very famous one. The program opens with local lore drawn from the preserve's own ground, the tales Washington Irving didn't make …

    $28.52
  • 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, more characters, and new performances make Twilight Village a must-visit destination for all ages in the Hudson Valley’s most legendary Halloween town. As evening settles …

    $25 – $35
  • Masque of the Red Death at Lyndhurst

    Masque of the Red Death at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    This October, Lyndhurst Mansion transforms into Prince Prospero’s abbey for an immersive theater experience drawn from Edgar Allan Poe’s The Masque of the Red Death. As a guest of Prospero, you’ll move through the Gothic halls of the 1842 mansion — dressed in the garish colors and grotesque beauty of Poe’s tale — walking room …

    $45
  • 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 dinosaurs, a working carousel, a planetarium built entirely of glowing gourds, and the Headless Horseman riding out of the dark. Arches, tunnels, and clearings open …

    $24 – $189
  • A Halloween Candlelight Experience in Sleepy Hollow

    Immaculate Conception, 199 N Broadway, Sleepy Hollow, NY 10591 199 N Broadway, Immaculate Conception, 199 N Broadway, Sleepy Hollow, NY 10591, NY, United States

    Step into the glow of hundreds of flickering candles this Halloween as Lumos Experiences brings its enchanting Classical Halloween concert to Sleepy Hollow. Set within the intimate surroundings of St. John Paul II Maronite Catholic Church at Immaculate Conception, this candlelit performance offers a hauntingly beautiful way to celebrate the season in the village that …

    $30 – $75
  • Headless Improv

    Headless Improv
    Fraternal Order of Eagles 322 N Broadway, Sleepy Hollow, NY

    Sleepy Hollow Arts Collective presents HEADLESS IMPROV An evening of spine-tingling comedy based on your suggestions! Something spooky is happening in Sleepy Hollow, and nobody knows what comes next, not even the performers. Headless Improv brings fast, fearless, completely unscripted comedy to the home of the Headless Horseman, with every scene invented on the spot …

    $25 – $30
  • Macbeth

    Macbeth
    Makers Central 84 Central Avenue, Tarrytown, NY, United States

    Anywhere Theatre Company presents a new vision of Macbeth: a demon-haunted world where Shakespeare’s Scottish king brings forth ancient forces that are terrifyingly real. As Macbeth descends into madness, the supernatural is no longer a metaphor – it is an ever-present force feeding his corruption. He wanted a kingdom. He awakened something else. Featuring an …

    $50
  • 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 journey through history under the glow of flickering flame. Your guide leads you past the resting places of titans of industry like Andrew Carnegie and …

    $50
  • Ghost Light: A Haunted Evening of Music, Movement, Poetry & Film

    Irvington Theater 85 Main Street, Irvington, NY, United States

    Enter the Irvington Theater after dark… if you dare. This Halloween, the theater comes alive with Ghost Light, a one-night-only, theatrical experience where music, poetry, theater, film, opera, and dance unfold throughout the space, creating a haunting tapestry of live performance. This multidisciplinary evening features a constellation of local artists including Rivers Edge Theater Company, …

    $30
  • Stevie’s Blue Lamp: A Stevie Nicks Tribute Band

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

    Channel your inner Stevie and celebrate the spooky season with everyone's favorite witchy woman! As the air turns crisp and the nights grow longer, Stevie’s Blue Lamp brings an evening of mystery, mood, and music to the Hudson River. Step into a world of velvet shadows, candlelit energy, and iconic songs that have defined generations. …

    $35 – $40
  • The Mavericks & Friends

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

    For three decades, The Mavericks carved out their Grammy-winning sound — a multicultural version of American roots music, blending stateside influences like country and rock & roll with the border-crossing textures of Cuban grooves, Tex-Mex twang, and Latin swagger — under the direction of Raul Malo. Raul wasn't just the band's frontman; he was its …

    $77.50 – $97.50
  • A Halloween Candlelight Experience in Sleepy Hollow

    Immaculate Conception, 199 N Broadway, Sleepy Hollow, NY 10591 199 N Broadway, Immaculate Conception, 199 N Broadway, Sleepy Hollow, NY 10591, NY, United States

    Step into the glow of hundreds of flickering candles this Halloween as Lumos Experiences brings its enchanting Classical Halloween concert to Sleepy Hollow. Set within the intimate surroundings of St. John Paul II Maronite Catholic Church at Immaculate Conception, this candlelit performance offers a hauntingly beautiful way to celebrate the season in the village that …

    $30 – $75
  • 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 journey through history under the glow of flickering flame. Your guide leads you past the resting places of titans of industry like Andrew Carnegie and …

    $50
  • TaSH Farmers Market

    Tarrytown and Sleepy Hollow Farmers Market
    Patriots Park Patriots Park, Tarrytown, NY, United States

    Stop by TaSH — the Tarrytown and Sleepy Hollow Farmers Market — for fresh Hudson Valley produce, meat, bread, cut flowers, dairy, preserves, wine and beer. There are weekly live music performances, children's activities, chef demos, and ongoing educational programs, plus weekly free samplings. Well-behaved dogs are welcome, provided your pooch is leashed. TaSH is …

    Free
  • Halloween at Collinwood: Daytime Meet & Greet

    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Dark Shadows returns to Lyndhurst for its 60th anniversary — and Collinwood opens its doors for an all-day Halloween celebration. Meet actress and author Kathryn Leigh Scott, beloved as Maggie Evans and Josette DuPres in the original series and House of Dark Shadows, along with other Dark Shadows guests appearing throughout the day. Roam the …

    $24 – $30
  • TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church

    418 North Broadway 418 North Broadway, Sleepy Hollow, United States

    Embark on a captivating journey through the rich history of Sleepy Hollow, where the echoes of colonial America come to life. Join our local historical society for a 90-minute immersive walking tour, starting with the tale of the first Dutch settlers who lived on Philipsburg Manor, one of the largest colonial estates in the Hudson River Valley. You …

    $28
  • 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 Manor, where the townsfolk of 1790 are waiting with their alibis. Fiery Hans Van Ripper, charming Katrina Van Tassel, spectral Hulda the Witch, and bold …

    $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 showcase hundreds of whimsical, vibrantly colored glass pumpkins. These one-of-a-kind works of art will be available for purchase. Proceeds support the Make-A-Wish® Hudson Valley Chapter. Food …

    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 Sleepy Hollow Cemetery. You'll get to know Washington Irving—the man behind the Headless Horseman, Ichabod Crane, and Katrina Van Tassel—and discover why the writer who …

    $20
  • Dark Shadows Walking Tour

    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    You've seen the mansion and the movies — now see the hidden corners of the estate where Dark Shadows was filmed. This guided walking tour explores the grounds for about an hour, visiting iconic exterior locations from both Dark Shadows films shot here at Lyndhurst. Two tours run that day: 11am–12pm and 1pm–2pm. The tour …

    $5
  • Tours of Historic Christ Church (Washington Irving’s Parish)

    Christ Church Tour
    Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United States

    Now expanded to four Saturdays this fall, join a guided tour through the history and architecture of historic Christ Church San Marcos, Washington Irving's own parish. See the beautiful stained glass memorial windows, learn the stories behind them, and visit Irving's marked pew along with other memorabilia from his years as warden and vestryman of …

    Free – $15
  • 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 the door to them. Myths & Mysteries is an hour-long guided tour through the National Historic Landmark that goes beyond architecture and furnishings to explore …

    $38
  • TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church

    418 North Broadway 418 North Broadway, Sleepy Hollow, United States

    Embark on a captivating journey through the rich history of Sleepy Hollow, where the echoes of colonial America come to life. Join our local historical society for a 90-minute immersive walking tour, starting with the tale of the first Dutch settlers who lived on Philipsburg Manor, one of the largest colonial estates in the Hudson River Valley. You …

    $28

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.