Postponed SUP Witches of Sleepy Hollow Festival
Searching for a wicked sight? Come to Kingsland Point Park for the 6th annual SUP Witches Paddle where the witches gather and “The Legend of Sleepy Hollow” is told. Join …
$8
25 events found.
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Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United States
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The Headless Horseman Files
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesImmerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane. Follow your guide on a mysterious 45-minute walk through the historic grounds of …
$25 – $30 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesBigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …
$24 – $50 -
Spirits of Sleepy Hollow Country
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesA Night of Legendary Magic Featuring Mark Clearview & Nick Wallace Join master illusionists as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks …
$65 -
The Headless Horseman Files
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesImmerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane. Follow your guide on a mysterious 45-minute walk through the historic grounds of …
$25 – $30 -
Spirits of Sleepy Hollow Country
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesA Night of Legendary Magic Featuring Mark Clearview & Nick Wallace Join master illusionists as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks …
$65 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesBigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …
$24 – $50 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesBigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …
$24 – $50 -
Hulda’s Night at Rockefeller State Park Preserve
Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United StatesHulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! …
$68 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesBigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …
$24 – $50 -
Hulda’s Night at Rockefeller State Park Preserve
Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United StatesHulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! …
$68 -
D&D Horror One-Shot: Tasha’s Madhouse
New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United StatesTasha's Madhouse: You travel to a small village, expecting a home-cooked meal and a night’s rest, but instead find nothing except for one boy sitting and weeping next to a …
$10 -
Spooky Board Games
New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United StatesGame Night at New Kawaii Join us on Wednesdays at 7PM for Game Night for Grown Ups and Young Adults (teens are welcome!) All October: Dare to Roll! The midweek …
$5 -
Hulda’s Night at Rockefeller State Park Preserve
Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United StatesHulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! …
$68 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesBigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …
$24 – $50 -
Hulda’s Night at Rockefeller State Park Preserve
Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United StatesHulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! …
$68 -
ShadowDark with a Dark(er) Twist
New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United StatesLooking for Players - no long-term commitment! Join DM Kevin for ShadowDark on Thursdays at 7 PM This October, the dice hold dark secrets… Join us for a run of …
$10 -
The Headless Horseman Files
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesImmerse yourself in this Sleepy Hollow whodunit and decide for yourself what really happened to Ichabod Crane. Follow your guide on a mysterious 45-minute walk through the historic grounds of …
$25 – $30 -
Hulda’s Night at Rockefeller State Park Preserve
Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United StatesHulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! …
$68 -
The Great Jack O’Lantern Blaze
Van Cortlandt Manor 525 S Riverside Avenue, Croton-on-Hudson, NY, United StatesBigger, Brighter, and More Spectacular Than Ever Before! The Great Jack O'Lantern Blaze is the Hudson Valley’s most electrifying fall happening! Meander through the 18th-century landscape of Van Cortlandt Manor …
$24 – $50 -
Spirits of Sleepy Hollow Country
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesA Night of Legendary Magic Featuring Mark Clearview & Nick Wallace Join master illusionists as they journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks …
$65 -
Hulda’s Night at Rockefeller State Park Preserve
Park Manager Residence 25 Sleepy Hollow Road, Sleepy Hollow, NY, United StatesHulda's Night at Rockefeller State Park Preserve is like nothing else you've ever experienced. Step back in time on this very special night in the woods of the real Sleepy Hollow! …
$68 -
Sleepy Hollow Haunted Hayride
Sleepy Hollow Village Hall 28 Beekman Avenue, Sleepy Hollow, NY, United StatesClimb aboard Sleepy Hollow’s annual 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 Hollow. Rumbling off …
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TaSH Farmers Market
Patriots Park Patriots Park, Tarrytown, NY, United StatesStop by TaSH, Tarrytown’s and Sleepy Hollow’s weekly farmers market, for fresh Hudson Valley produce, meat, bread, cut flowers, dairy products, preserves, wine, and beer. There are weekly live music performances, …
Free -
Christ Church/San Marcos 186th Annual Fall Fair
Christ Church San Marcos 43 South Broadway, Tarrytown, NY, United StatesChrist Episcopal Church in Tarrytown, where Washington Irving once worshipped, is thrilled to bring back its Fall Fair in 2025! From 10 am to 4 pm, visitors can shop for …
Free
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.