The Spookiest Halloween Events and Activities in the Hudson Valley

The Great Jack O Lantern Blaze is back, among other scary things to do this Halloween.

photo by tom nycz for historic hudson valley

Great Jack O Lantern Blaze

Van Cortlandt Manor, Croton-On-Hudson

September 20–November 30

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Come to historic Van Cortlandt Manor for a tradition unlike any other. Spectacle and awe are on the agenda, as dioramas, sculptures, and even a carousel made out of grinning, flame-licked pumpkins populate the grounds.


The Haunted History Pub Crawl


October 10–29

This special tour is for those who prefer their ghost stories seasoned with history and a slight buzz. Docents lead you through a haunted mansion and to ghost-occupied pubs offering spookily convenient drink specials.

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Broadway Fright Night

The Emelin Theater, Mamaroneck

October 25

Great White Way regulars like Mike McGowan and Jenny Lee Stern take on the stage songbook’s creepiest numbers, with selections from Little Shop of Horrors, Wicked, Phantom of the Opera, Sweeney Todd, and more. Tickets start at $55.


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photo courtesy of headless horseman hayrides & haunted houses

Headless Horseman Hayrides & Haunted Houses

Ulster Park

September 21–November 2

The high-tech and low-culture thrills of Headless Horseman return with a set of brand-new houses, mazes, and hayrides for 2019. Expect Hollywood-quality costumes, booming sound, and a unique show from illusionist Ryan Dutcher.


photocourtesy of nys parks, recreation, and historic preservation

Legends by Candlelight Ghost Tours

Clermont State Historic Site, Germantown

October 18–26

As landowners and landbarons, the Livingstons engaged in acts far spookier – and legally dodgier – than anything Irving ever wrote. Why not haunt their historic abode with this special ghost tour, lit by flickering jack-o-lanterns and followed by roasted marshmallows?


photo by tom nycz for historic hudson valley

The Unsilent Picture

Philipsburg Manor, Sleepy Hollow

Weekends through November 3

An original silent film starring Bill Irwin, accompanied by live musicians and a special effects Foley artist. Inspired by Washington Irving’s The Adventure of the Mysterious Picture, the film was shot nearby on location at historic Van Cortlandt Manor.


photo by tom nycz for historic hudson valley

Horseman’s Hollow

Philipsburg Manor, Sleepy Hollow

October 4–31

For a somewhat less-faithful, but no less creepy, take on the Irving story, this extensive haunted walk should do the trick. The historic Philipsburg Manor grounds are turned into a landscape of the dead and the undead, telling the story of a town driven to madness by the Headless Horseman.


Hudson Horrors

Rye Playland, Rye


A chilling, thrilling addition to the lighthearted attractions traditionally found at Rye Playland, Hudson Horrors is an interactive, immersive experience that takes unsuspecting visitors through three equally terrifying experiences. Part theater performance, part haunted house, the hour-long tour captivates with storytelling, a musical score, and surprise performances that will leave locals spooked to the core.

photo by BreeAnne Clowdus

Sleepy Hollow Experience

October 4–November 3

Washington Irving’s Sunnyside, Tarrytown

Irving’s classically American ghost story gets its own theatrical experience at this special outdoor show. Live music, immersive effects, seasonal drinks, and more bring Ichabod Crane to life at the site of his creation.



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