The Goblin Market
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
25 events found.
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Events
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Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United States
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Christ Church/San Marcos Annual Fall Fair
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesChrist 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
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesFour 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 121 North Broadway, Tarrytown, NY, United StatesFall 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
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesJoin 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 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe 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 …
$20 -
Trick-or-Treat Weekend at Lyndhurst
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesOn 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
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United StatesA 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 -
TarryHollow: Sleepy Hollow, Irving and the Old Dutch Church
418 North Broadway 418 North Broadway, Sleepy Hollow, United StatesEmbark 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, …
$28 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe 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 …
$20 -
An Audience with Poe
Historic Hudson Valley 639 Bedford Road, Tarrytown, United StatesSip, 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
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesSleepy 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 Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe 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 …
$20 -
The Lady in White
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United StatesAn 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 …
$58 -
Irving’s Legend at Sunnyside
Sunnyside 3 W Sunnyside Lane, Irvington, NY, United StatesHear 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 Lady in White
Armour-Stiner Octagon House 45 W Clinton Avenue, Irvington, NY, United StatesAn 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 …
$58 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesMore 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
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe 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
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesWhere 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 -
The Legend of Sleepy Hollow at Old Dutch Church
Old Dutch Church 430 North Broadway, Sleepy Hollow, NY, United StatesDon’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 …
$40 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesStep 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 …
$50 -
Sleepy Hollow Haunted Hayride
Sleepy Hollow Village Hall 28 Beekman Avenue, Sleepy Hollow, NY, United StatesClimb 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 …
$50 -
Peek-a-Boo (An Immersive Hudson Valley Haunt)
Bethany Arts Community 40 Somerstown Road, Ossining, NY, United StatesBack by popular demand, River’s Edge Theatre Company and Bethany Arts Community are teaming up for the third year in a row to remount the wildly provocative Peek-a-Boo (An Immersive …
$27 – $47 -
Yellow Brick Joel: The Tribute Concert featuring David Clark and Bill Connors
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesStep into a world of timeless melodies and unforgettable piano anthems with Yellow Brick Joel: The Tribute Concert! This incredible live show features David Clark, a masterful performer who brings …
$47.50 – $63.55 -
Murder and Mayhem Walking Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesThe 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
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.