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  • 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 produce, seafood and meats, cheese, pickles, prepared foods and baked goods, with live music most weeks. The Irvington Farmers Market runs Sunday mornings outdoors on …

    Free
  • Gothic Market Weekend at Lyndhurst

    Gothic Market Weekend at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    Gothic Market Weekend returns to Lyndhurst Mansion in Tarrytown for three days — Friday, October 23rd through Sunday, October 25th, 2026, from 9am to 5pm. Set against the mansion's dramatic Gilded Age backdrop, the market brings together a curated lineup of Hudson Valley vendors selling spooky oddities, curated antiques, gothic jewelry, and witchy wares, plus …

    $29 – $35
  • 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
  • Glass Pumpkin Patch Fundraiser

    Glass Pumpkin Patch Fundraiser
    Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States

    The Village of Sleepy Hollow welcomes back the artists from the Adirondack Glassblowing Studio for the 4th annual Glass Pumpkin Patch Fundraiser in Kingsland Point Park. This festive event will showcase hundreds of whimsical, vibrantly colored glass pumpkins. These one-of-a-kind works of art will be available for purchase. Proceeds support the Make-A-Wish® Hudson Valley Chapter. Food …

    Free
  • 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
  • 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

    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
  • Sleepy Hollow Oktoberfest

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

    German food and beer, live Bavarian music, and the Hudson at your back — Sleepy Hollow's Oktoberfest returns for its 14th year. After being postponed due to weather, the Sleepy Hollow Oktoberfest is back on Sunday, October 25th, at Kingsland Point Park! Enjoy an afternoon of German food, desserts, adult beverages, live music, and more along the Hudson River. This …

    Free – $5
  • 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 the banks of the Hudson River. Set against sweeping views of the Governor Mario M. Cuomo Bridge, the festival pairs the laid-back marina atmosphere The …

    Free
  • 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
  • A Very Grimm Story Spooktacular with Adam Gidwitz

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

    The fairy tales you thought you knew are about to get a Grimm makeover—live on stage! This family-friendly event brings the hit podcast Grimm, Grimmer, Grimmest to life for an afternoon of storytelling, laughter, and spooky season fun. Join award-winning author and host Adam Gidwitz (A Tale Dark & Grimm, Max in the House of …

    $30 – $50
  • 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
  • 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 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
  • 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
  • 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
  • Slapering Hol Press Presents the Debut Poets Reading

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

    Join us in-person at the Hudson Valley Writers Center for an afternoon of terrific poetry from Ellen Goldsmith, Richard Parisio, Avia Tadmor, and Zoë Ryder White. Hosted by the editors of Slapering Hol Press (SHP). Ellen Goldsmith’s first full length collection, Are We There Yet? (Kelsay Books) follows four chapbooks. Her first, No Pine Tree in …

    Free
  • 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 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 Legend of Sleepy Hollow and Local Lore

    The Legend of Sleepy Hollow and Local Lore
    Rockwood Hall Phelps Way, Pleasantville, NY, United States

    Follow a lamplit path to the ruins of Rockwood Hall, high above the Hudson, where storyteller and author David Neilsen is waiting with an evening of Sleepy Hollow's lesser-known ghost stories — and one very famous one. The program opens with local lore drawn from the preserve's own ground, the tales Washington Irving didn't make …

    $28.52
  • 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
  • Masque of the Red Death at Lyndhurst

    Masque of the Red Death at Lyndhurst
    Lyndhurst 635 South Broadway, Tarrytown, NY, United States

    This October, Lyndhurst Mansion transforms into Prince Prospero’s abbey for an immersive theater experience drawn from Edgar Allan Poe’s The Masque of the Red Death. As a guest of Prospero, you’ll move through the Gothic halls of the 1842 mansion — dressed in the garish colors and grotesque beauty of Poe’s tale — walking room …

    $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
  • 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

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.