• 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
  • 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 are encouraged to wear costumes and hunt for candy at special stops throughout the grounds (bring your own treat bag!). For an extra dose of …

    $5 – $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 …

    $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 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 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 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
  • 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
  • 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
  • Hocus Pocus Family Movie Screening & Fun Facts with Shannon Carlin

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

    See the movie. Hear the stories. Celebrate the magic. Gather the whole family for a screening of this Halloween classic! After the film, stick around for a special conversation with …

    Free – $12
  • 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
  • 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
  • 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
  • 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, …

    $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

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.