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  • 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 of Sleepy Hollow Country — not generic stage spooks, but the local dead. Hulda of Bohemia, the healer the village called a witch. Major John André, the British spy …

    $65 – $89
  • A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.

    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

  • ‘Tis the Wind and Nothing More

    ‘Tis the Wind and Nothing More
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    An immersive Halloween-season tour with a performance of "The Raven" at the Armour-Stiner Octagon House, Irvington, NY For two October weekends only, the Armour-Stiner Octagon House goes back more than a century to host a literary evening. Guests are welcomed as visitors to the annual salon of Jessie Clarke, one of the most puzzling people …

    $58

  • 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

  • ‘Tis the Wind and Nothing More

    ‘Tis the Wind and Nothing More
    Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United States

    An immersive Halloween-season tour with a performance of "The Raven" at the Armour-Stiner Octagon House, Irvington, NY For two October weekends only, the Armour-Stiner Octagon House goes back more than a century to host a literary evening. Guests are welcomed as visitors to the annual salon of Jessie Clarke, one of the most puzzling people …

    $58

  • The Masquerade of the Red Death

    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Step into a night of gothic splendor and inescapable doom at The Masquerade of the Red Death Halloween Party. Held within the soaring, vaulted Gothic halls of Lyndhurst Mansion, this exclusive gathering transforms our historic estate into Prince Prospero’s final, desperate refuge. Guests will indulge in opulent revelry, completely shut off from the outside world, …

    $120
  • This is a view of the 2022 Great Jack O'Lantern Blaze at Van Cortlandt Manor in Corton-on-Hudson, N.Y. on September 14, 2022.

    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

  • 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
  • One participant in Murder Mystery night at Sleepy Hollow Cemetery interviews a second participant.

    Murder Mystery

    Murder Mystery!
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Join us for a Murder Mystery experience as we celebrate Washington Irving's "The Legend of Sleepy Hollow"! "The Legend of Sleepy Hollow" was published just over 200 years ago, and the literate world is holding a convention to celebrate! Plus, convention organizers promise a spectacular revelation--the discovery of Irving's initial draft, which is scheduled to …

    $65
  • Sleepy Hollow Cemetery tour pauses at the entrance to Archbold mausoleum.

    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
  • Sepia-toned promotional image with a portrait of poet Minna Irving on the left and the Wallace family monument, marking the grave of chocolatier William Wallace, on the right at Sleepy Hollow Cemetery.

    The Good, the Bad and the Unusual-Cemetery Tour

    The Good, the Bad and the Unusual-Cemetery Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Join Sara Mascia and Tara Van Tassell of our local historical society as they share stories of intriguing residents and some of Sleepy Hollow Cemetery's world-famous inhabitants—and let you guess who counts as good, bad, or unusual. You'll meet locals like poet and eccentric Minna Irving, chocolatier William Wallace, and beloved neighbor "Uncle" Washington Irving, …

    $50
  • This is a photo montage for Margaret Cho at Tarrytown Music Hall.

    Margaret Cho: Choligarchy

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

    Comedian. Actor. Musician. Advocate. Entrepreneur. Five-time Grammy and Emmy nominee. When hasn’t Margaret Cho’s strong voice been part of our consciousness? It feels like she has always been here, like a friend you can always count on, lighting the path for other women, other members of underrepresented groups, other performers, to follow. Margaret staunchly supports …

    $46 – $76
  • Sleepy Hollow Cemetery tour pauses at the entrance to Archbold mausoleum.

    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
  • Fresh produce from Berry Brook Farm at Tarrytown and Sleepy Hollow Farmers Market.

    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

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

    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
  • Headless Horseman Files at Philipsburg Manor.

    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
  • This is a photo montage for Ghost Tours at Tarrytown Music Hall.

    Ghost Tours of Tarrytown Music Hall

    Ghost Tours of Tarrytown Music Hall
    Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United States

    Join this guided tour created by Master Storyteller Jonathan Kruk and discover the historic lore and spirits that linger at The Tarrytown Music Hall. The Tarrytown Music Hall was built in 1885 during the Millionaire’s Colony Era when mansions dotted the Hudson Valley landscape and families such as the Rockefellers, Goulds and Vanderbilts gathered at the Music …

    $29
  • A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.

    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
  • This is a banner ad for tours of Christ Church in Tarrytown, NY.

    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

    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
  • A performer on stage at Sleepy Hollow Music Festival in Sleepy Hollow, NY.

    Sleepy Hollow Music Festival

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

    Eleven bands on two stages, a costume parade, and the Headless Horseman galloping past the stage between sets — the third annual festival that opens Sleepy Hollow's Halloween season. Main Stage brings the 90s: Everclear, the Smithereens featuring Marshall Crenshaw, Fastball, SoulShine: An Allman Brothers Experience, and Anthony Giaccio & the Assortments. The Regional Stage …

    $62.5 – $185
  • A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.

    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

  • 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 of Sleepy Hollow Country — not generic stage spooks, but the local dead. Hulda of Bohemia, the healer the village called a witch. Major John André, the British spy …

    $65 – $89
  • A Sleepy Hollow Cemetery walking tour pauses at the gate to Washington Irving's family lot.

    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

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.