• Open Mic Night

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

    Physical and virtual doors open at 7:20 pm for event starting at 7:30 pm. Due to popular demand to participate, we’ve had to limit the amount of readers to 20. …

    Free – $5
  • Mary Shelley's Frankenstein

    Mary Shelley’s Frankenstein
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Shelley's classic tale of man and monster comes to life! Think you know the story? Think again. Come enjoy this Gothic tale of hubris, vengeance, and poetic justice adapted from …

    $45
  • 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 …

    Free
  • The Goblin Market

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

    Hudson Valley Writers Center opens its historic building for an October pop up with local artists and creators! Drop in for artwork, crafts, and other goods from Sleepy Hollow creators. …

    Free
  • Christ Church/San Marcos Annual Fall Fair

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

    Christ Church San Marcos, the historic Episcopal parish in Tarrytown where Washington Irving once worshipped, brings back its beloved Fall Fair on October 17, 2026, from 10 am to 4 …

    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
  • Warner Library Fall Book Sale

    Warner Library Book Sale
    Warner Library 121 North Broadway, Tarrytown, NY, United States

    Fall for a good book at the Warner Library Fall Book Sale! As the leaves turn and the crisp air settles over Sleepy Hollow Country, the Warner Library invites you …

    Free
  • 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 …

    $29
  • Trick-or-Treat Weekend at Lyndhurst

    Trick-or-Treat Weekend at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    On Saturday, October 17th and Sunday, October 18th, 2026, Lyndhurst Mansion in Tarrytown invites families to a festive weekend of trick-or-treating across its historic 67-acre landscape. Kids and grown-ups alike …

    $5 – $30
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Sleepy Hollow Haunted Hayride

    Sleepy Hollow Haunted Hayride
    Sleepy Hollow Village Hall 28 Beekman Avenue, Sleepy Hollow, NY, United States

    Climb aboard the Sleepy Hollow Haunted Hayride and hold on to your head! All seems well when you board your hay wagon in the brightly lit streets of downtown Sleepy Hollow. The journey begins innocently enough. Rumbling off into the dark you realize too late you are heading down the Albany Post Road, past the …

    $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 …

    $60