Sponsored

  • 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
  • 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
  • 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
  • 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
  • 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
  • Murder and Mayhem Walking Tour

    Murder and Mayhem Walking Tour
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    The true stories on this two-hour lantern tour of Sleepy Hollow Cemetery are so grim, you just might have nightmares! Curious to learn about a family that lost 5 children one terrible afternoon, or a horrific murder that led police on a multi-state chase? Maybe you’d like to hear about a son who shot his …

    $60
  • The New Pornographers – The Former Site Of Tour

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

    Over the past 20+ years, The New Pornographers have proven themselves one of the most excellent bands in indie rock. They have released nine studio albums, including their classic debut Mass Romantic and their latest 2023’s Continue as a Guest. The band’s new album The Former Site Of will be out via Merge Records on …

    $43 – $73
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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 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
  • 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
  • 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 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
  • 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

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.