Sleepy Hollow Halloween 10K
The Headless Horseman sends off costumed runners from Beekman Avenue on a 6.2-mile loop through some of the most storied ground in American literature. The certified USATF course winds through …
$45 – $55
25 events found.
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Morse School 30 Pocantico Street, Sleepy Hollow, NY, United States
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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 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 -
Glass Pumpkin Patch Fundraiser
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesThe 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 …
Free -
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 -
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 -
Tarrytown Halloween Parade
Patriots Park Patriots Park, Tarrytown, NY, United StatesParking in the Villages of Tarrytown and Sleepy Hollow will be extremely limited on the night of the Halloween Parade due to road closures. The Halloween Parade urges you to use …
Free -
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 Legend of Sleepy Hollow and Local Lore
Rockwood Hall Phelps Way, Pleasantville, NY, United StatesFollow 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 …
$28.52 -
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 -
Masque of the Red Death at Lyndhurst
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesThis 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, …
$45 -
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 -
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 -
Headless Improv
Fraternal Order of Eagles 322 N Broadway, Sleepy Hollow, NYSleepy Hollow Arts Collective presents HEADLESS IMPROV An evening of spine-tingling comedy based on your suggestions! Something spooky is happening in Sleepy Hollow, and nobody knows what comes next, not …
$25 – $30 -
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 -
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 -
The Rocky Horror Picture Show
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesRESERVE YOUR SPECIAL AUDIENCE PARTICIPATION KIT WITH YOUR TICKETS! In this cult classic, sweethearts Brad (Barry Bostwick) and Janet (Susan Sarandon), stuck with a flat tire during a storm, discover …
$28 – $36
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.