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 -
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 …
$25 -
The Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …
$20 -
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 -
Lyndhurst After Dark!
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesLyndhurst After Dark offers an exquisite Halloween experience, blending gothic charm with subtle spookiness. You've experienced the splendor of the Lyndhurst Mansion during the day, but have you seen it …
$20 – $40 -
Sleepy Hollow Show & Tell
Hudson Valley Writers Center 300 Riverside Drive, Sleepy Hollow, NY, United StatesBack for round 3! Another Halloween edition of this weird and wonderful series of neighbors+strangers sharing objects+stories, this time again at the cozy Hudson Valley Writers Center. Oct. 16th 7pm. …
$10 – $20 -
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 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesStep back in time and explore the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous. You’ll …
$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 -
Peek-a-Boo (An Immersive Hudson Valley Haunt)
Bethany Arts Community 40 Somerstown Road, Ossining, NY, United StatesAfter a sold-out run in 2024, River’s Edge Theatre Company is bringing its provocative immersive show Peek-a-Boo back to Bethany Arts Community this October. Inspired by hidden histories of the …
$30 – $35 -
Pink Martini All Stars
Tarrytown Music Hall 13 Main Street, Tarrytown, NY, United StatesNow in its 31st year, the unstoppable engine of joy that is Pink Martini continues to bring founder Thomas Lauderdale’s mission of multi-cultural connection and inclusion to concert stages on …
$67.50 – $97.50 -
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 Original Knickerbocker Tour
Sleepy Hollow Cemetery South Gate 430 North Broadway, Sleepy Hollow, NY, United StatesThe Original Knickerbocker: Washington Irving & “The Legend of Sleepy Hollow”. Meet the father of the American short story on this one-hour tour of Sleepy Hollow Cemetery! Learn all about …
$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. This fall, professional storytellers bring to life the “powerful graphic effect” that Washington Irving …
$60 -
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 -
Sleepy Hollow Rock & Roll House of Horrors
Holy Cross Parish Hall 116 Beekman Avenue, Sleepy Hollow, NY, United StatesDescend in to the basement of an abandoned church rectory and witness new scares with new twists!!! Be careful what you wish for…Enter if you dare! Get your tickets now. …
$30 – $35 -
Lyndhurst After Dark!
Lyndhurst 635 South Broadway, Tarrytown, NY, United StatesLyndhurst After Dark offers an exquisite Halloween experience, blending gothic charm with subtle spookiness. You've experienced the splendor of the Lyndhurst Mansion during the day, but have you seen it …
$20 – $40 -
Twilight Village at Sleepy Hollow
Philipsburg Manor 381 North Broadway, Sleepy Hollow, NY, United StatesWhere the Legend Lives After Dark! As evening settles over Philipsburg Manor, channel the spirit of Irving’s famously creepy tale at this immersive outdoor experience with live storytellers, fire performers, …
$25 – $30 -
Sherlock Holmes and the Legend of Sleepy Hollow
Makers Central 84 Central Avenue, Tarrytown, NY, United StatesIn this spine-tingling and laugh-filled theatrical thrill ride, Sherlock Holmes and Dr. John Watson leave the foggy streets of London behind for the eerie woods of Sleepy Hollow! A rash …
$50 -
Sleepy Hollow Cemetery Lantern Tour
Sleepy Hollow Cemetery North Gate 540 North Broadway, Sleepy Hollow, NY, United StatesStep back in time and explore the cemetery by kerosene lantern light! This two-hour evening tour gives you a great overview of why Sleepy Hollow Cemetery is so famous. You’ll …
$50
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.