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 -
SUP Witches Festival
Kingsland Point Park 299 Palmer Avenue, Sleepy Hollow, NY, United StatesHundreds 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, …
Free – $10 -
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 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 -
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 -
Pokeween Event
New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United StatesPokéween Celebration! Ticket includes - special treats and spooky beverages. All ages welcomed! This is a casual league, drop in anytime after 6 PM and bring your deck! Lavender Town …
$10 -
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 Halloween 10K
Morse School 30 Pocantico Street, Sleepy Hollow, NY, United StatesEnjoy a remarkable course that takes you through Historic Sleepy Hollow’s treasured sights including a stretch along the Hudson River with views of the Headless Horseman Bridge, Sleepy Hollow Cemetery …
$45 – $55 -
Kids Halloween Craft Party
New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United StatesKids are invited to celebrate Halloween at New Kawaii with our Spooky Saturday Craft Party! We're making pumpkins, spiderwebs and other spooky projects! Costumes are welcome. Children ages 5 and …
$15 -
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 -
Horror in the Cornfield RPG One-Shot
New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United StatesHorror in the Cornfield: a Shadowdark One-Shot Role Playing Game. Open to new players and those experienced with the Shadowdark system. $15 - includes a treat and beverage A creepy and …
$15
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.