D&D Horror One-Shot: Tasha’s Madhouse
Tasha'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
25 events found.
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New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United States
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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, …
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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 -
Warner Library Fall Book Sale
Warner Library 121 North Broadway, Tarrytown, NY, United StatesVisit the Warner Library on Saturday, October 18, and Sunday, October 19, from 10 am to 5 pm for the Friends of the Warner Library Book Sale. The Friends will …
Free -
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 -
Spooky (but not too) Scary Stories
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesWhat makes kids Happy for Halloween? SPOOKY (But not too) SCARY STORIES! Told by Legendary Storyteller, Jonathan Kruk at the Tarrytown Music Hall. Frightful fun with tales of the The …
$29 -
Indie RPG One-Shot: Never Going Home
New Kawaii 1 Bridge Street, Suite 105, Irvington, NY, United StatesCharacters will be provided for this one-shot. Limited seats - early registration is highly recommended. Adults and teens 16+ Join New Kawaii for the next entry in our monthly Indie …
$10 -
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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Irvington Farmers Market
Main Street School 101 Main Street, Irvington, NY, United StatesEnjoy live music, river views and a laid-back setting at this small-town Sunday market showcasing the best of what the Hudson Valley has to offer. In season, there is fresh …
Free -
Warner Library Fall Book Sale
Warner Library 121 North Broadway, Tarrytown, NY, United StatesVisit the Warner Library on Saturday, October 18, and Sunday, October 19, from 10 am to 5 pm for the Friends of the Warner Library Book Sale. The Friends will …
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.