Sponsored

  • Yonder Mountain String Band

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

    Grammy-nominated Yonder Mountain String Band set the tone for a new way forward in acoustic music, carrying bluegrass into rooms and conversations it had never reached before. Nearly three decades later, that same spirit still guides them, alive and present on Good As True (2026), the band’s 12th studio album. The record captures Yonder in …

    $49.50 – $59.50
  • H. G. Wells The Time Machine

    H. G. Wells The Time Machine
    Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United States

    Join The Time Traveller as he recounts his epic journey into the distant future in this adaptation of H.G. Wells' classic novel, performed by David Neilsen. Is his tale of Eloi, Morlocks, and a world both pristine and dangerous a figment of his imagination — or an ominous glimpse into our own dystopian future? Visit …

    $45
  • 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
  • Rocky’s 5k

    Rockefeller State Park Preserve 125 Phelps Way, Pleasantville, NY, United States

    Beautiful fall foliage is the perfect backdrop for Rocky’s 5K. Challenging hills and wide carriage roads – the perfect race for experienced trails runners and first timers. If you are familiar with the Rockefeller State Park Preserve course, test your stamina and charge those uphills! First race? The Rocky’s 5K well-marked course and friendly volunteers will make it enjoyable from …

    $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
  • 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
  • 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
  • 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
  • Tours of Historic Christ Church (Washington Irving’s Parish)

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

    Now expanded to four Saturdays this fall, join a guided tour through the history and architecture of historic Christ Church San Marcos, Washington Irving's own parish. See the beautiful stained glass memorial windows, learn the stories behind them, and visit Irving's marked pew along with other memorabilia from his years as warden and vestryman of …

    Free – $15
  • 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
  • TarryHollow: Sleepy Hollow, Washington Irving y la Antigua Iglesia Holandesa

    418 North Broadway 418 North Broadway, Sleepy Hollow, United States

    ¡Embarcamos en un viaje cautivador de la historia de Sleepy Hollow, donde aún se respira la época colonial! Acompáñanos en una visita guiada de 90 minutos llena de historia; iniciando con el relato de los primeros colonos Holandeses que se establecieron en Philipsburg Manor (una de las más grandes fincas coloniales del valle del Río …

    $28
  • SUP Witches Festival

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

    Hundreds of costumed witches, warlocks, and wizards paddle the Hudson River off Kingsland Point Park in one of Sleepy Hollow's signature Halloween traditions. On shore, "Witches Hollow" brings live music, food, local brews, and vendors; on the water, a mass costumed paddle launches in the early afternoon for a group photo taken mid-river. It's been …

    $8 – $35
  • 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
  • Sleepy Hollow: Fact & Fiction with J.W. Ocker

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

    Get an exclusive glimpse into local folklore and history from popular podcaster and bestselling author J.W. Ocker, whose brand-new book, Chasing the Headless Horseman (Countryman Press, Sept. 2026), investigates how a quiet riverside village became a global phenomenon and why Washington Irving’s gothic legend has endured for more than two centuries. Ocker will talk about …

    $35
  • 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
  • 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 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 Fright Fest

    Home for Horror: Sleepy Hollow Cinema
    Kusel Auditorium at Sleepy Hollow High School 210 North Broadway, Sleepy Hollow, NY, United States

    Sleepy Hollow Cinema is launching the 1st year of a national short-film competition for young horror filmmakers — high schoolers and undergrads screened right here in the Halloween Capital of the World! Experience bold short horror films* from rising student filmmakers around the country. Who will claim the coveted Golden Horseman Trophy? Join us to …

    Free
  • 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

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.