• 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
  • The Legend of Sleepy Hollow at Old Dutch Church

    Old Dutch Church 430 North Broadway, Sleepy Hollow, NY, United States

    Don’t miss your chance to experience "The Legend of Sleepy Hollow" in the heart of Sleepy Hollow! On October 10, 11, 17, 18, 24, and 25 at 7 p.m., the historic Old Dutch Church becomes the perfect stage for Washington Irving’s haunting tale. With glowing lanterns and spellbinding performances, you'll encounter iconic characters like Ichabod …

    $40
  • Kevin Nealon

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

    Emmy and SAG-nominated actor, comedian, and author Kevin Nealon is best known for his nine-year stint as a cast member of NBC’s Saturday Night Live, and has received critical acclaim for his role in the Showtime series Weeds. Kevin most recently starred on the CBS-TV comedy series Man With A Plan, produces and hosts digital …

    $46.50 – $63.50
  • Dr. Jekyll and Mr. Hyde

    The Strange Case of Dr. Jekyll and Mr. Hyde
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    The Strange Case of Dr. Jekyll and Mr. Hyde One man, two natures. The brilliant Dr. Henry Jekyll is convinced that the evil in man is a quality that can be stripped away from his soul. But when he experiments upon himself to prove his point, he gives that evil a chance to roam free …

    $45
  • 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 …

    $60
  • Irvington Farmers Market

    Irvington Farmers Market
    Main Street School 101 Main Street, Irvington, NY, United States

    Enjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there's fresh local …

    Free
  • 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
  • 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
  • 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
  • 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
  • An Afternoon of Poetry with Kathy Fagan, Erika Meitner, and Elaine Sexton

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

    Please join us at 2:00 p.m. on October 11 for an afternoon of new poetry from Kathy Fagan, Erika Meitner, and Elaine Sexton! Kathy Fagan’s newest collection is The Unbecoming (W.W. Norton, September 2026). Her sixth book, winner of PSA’s William Carlos Williams Poetry Prize, is Bad Hobby (Milkweed Editions, 2022), available in print and …

  • 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
  • ‘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
  • 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 in Edgar Allan Poe’s writing, with haunting renditions of The Raven, The Tell-Tale Heart, The Black Cat, and The Masque of the Red Death. We …

    $65
  • ‘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
  • An Evening of Spirit Connection with Mediums Daisy & Arlene

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

    Get ready for an unforgettable evening of insight, healing, and messages from beyond. The world is awakening in powerful ways, and more people than ever are feeling drawn to explore the unseen, the unknown, and the deeper meaning of life. Daisy and Arlene are two mediums and soul sisters with a deep, undeniable connection. When …

    $35 – $40
  • 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 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
  • Bram Stoker’s Dracula

    Bram Stoker’s Dracula
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Bram Stoker's Dracula comes to life for one night only at Sleepy Hollow Cemetery's Washington Irving Memorial Chapel. This adaptation, drawn from Stoker's original 1897 text, follows the bloodthirsty Count, his naive solicitor Jonathan Harker, and vampire hunter Dr. Abraham Van Helsing in the Gothic horror tale that started it all. The Headless Horseman isn't …

    $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, 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
  • Bram Stoker’s Dracula

    Bram Stoker’s Dracula
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Bram Stoker's Dracula comes to life for one night only at Sleepy Hollow Cemetery's Washington Irving Memorial Chapel. This adaptation, drawn from Stoker's original 1897 text, follows the bloodthirsty Count, his naive solicitor Jonathan Harker, and vampire hunter Dr. Abraham Van Helsing in the Gothic horror tale that started it all. The Headless Horseman isn't …

    $45

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.