There’s no better way to celebrate the spooky season than by experiencing Historic Hudson Valley’s legendary Halloween events in Sleepy Hollow Country. From the jaw-dropping Great Jack O’Lantern Blaze to live retellings of Washington Irving’s classic tale and eerie tours through one of the world’s most haunted cemeteries, this region is the ultimate Halloween destination. Read on for our favorite events and must-see attractions that make Sleepy Hollow truly come alive this season.
The Great Jack O’Lantern Blaze
No need to wait for the Great Pumpkin to appear to see a Halloween display, head to the famous Great Jack O’Lantern Blaze! The Blaze is an annual Halloween extravaganza in the Hudson Valley with over 7,000 carved jack o’ lanterns and pumpkin sculptures that brings in over 175,000 visitors each year! The Blaze has been completely reimagined for 2025 – and is bigger, better, and more spectacular than ever, with new pumpkin displays including iconic New York landmarks and a WICKEDLY fun Wizard of Oz themed display. Interested in tickets? Act quick! Days and times sell out in advance.
The Great Jack O’Lantern Blaze. Runs through early November. Van Cortlandt Manor. 525 S Riverside, Croton-on-Hudson, NY 10520. More information HERE.
Twilight Village
When evening falls over Philipsburg Manor, Twilight Village comes alive with live storytellers, fire performers, eerie encounters, and an enchanting pop-up market full of curiosities. Mingle with Sleepy Hollow legends, catch tarot readings, ride the energy of a roaming band, and brace yourself — the Headless Horseman makes a dramatic appearance in a sound-and-light spectacle you won’t forget. Twilight Village. Runs through November 1st. Philipsburg Manor: 381 N Broadway, Sleepy Hollow, NY. More information HERE.
The Headless Horseman Files
Step into a chilling Sleepy Hollow whodunit with The Headless Horseman Files, where attendees become investigators retracing the last known steps of Ichabod Crane. Haunted clues, atmospheric sets, and interactive storytelling invite you to decide for yourself what really happened that fateful night in the Hollow. The Headless Horseman Files. 45 minute guided tour. Runs through November 1st. Philipsburg Manor: 381 N Broadway, Sleepy Hollow, NY. More information HERE.
The Spirits of Sleepy Hollow Country
Master illusionists journey into the realm of the unknown at this spooky supernatural spectacle. Their tricks and conjurings will leave you spellbound as they communicate with the spirits of Sleepy Hollow Country, like Hulda, Major Andre, and the Headless Horseman himself! Once thought long departed, it turns out these spirits are still present and have quite a bit to say. Note: the show is strongly recommended for ages 10+ only. The Spirits of Sleepy Hollow Country. 381 N Broadway, Sleepy Hollow, NY. Tickets and more info HERE.
Cemetery of Sleepy Hollow
A trip to area isn’t complete without a visit to Sleepy Hollow Cemetery and its famous residents. Elizabeth Arden, Brooke Astor, Walter Chrysler, Washington Irving, and William Rockefeller, among thousands of others, are buried here in these grounds adjacent to the Old Dutch Church. Even more famous than these residents is how the cemetery is forever linked to one of the best known Halloween tales, The Legend of Sleepy Hollow. In the story written by Washington Irving, Ichabod Crane is chased towards the Old Dutch Burying Grounds by a Headless Horseman. The cemetery’s connection to the story doesn’t stop there; Irving, himself, is buried here. This cemetery has it all – decaying 18th century headstones, twisting narrow paths, and eerie metal gates, all makes for a straight-out-of-a-movie Halloween scene that simply cannot be replicated anywhere else. A must see. Sleepy Hollow Cemetery. 540 North Broadway, Sleepy Hollow, NY. More information on the cemetery HERE.
Irving’s ‘Legend’
The Legend of Sleepy Hollow as you have never seen before! Performed outdoors under the stars (tented in rain) at Washington Irving’s Sunnyside estate, master storyteller Jonathan Kruk casts a spell with dramatic performances of the classic tale. Live music, puppets, and an appearance from the Headless Horseman himself make this a spooky spectacular experience for all ages. Irving’s ‘Legend’. 13 W Sunnyside Lane, Irvington, NY More information and tickets HERE.
Horsefeathers
Scare up an appetite? Grab a bite at the charming Horsefeathers in Tarrytown, which is just a short drive from the Sleepy Hollow Cemetery. Serving up to 100 different menu items daily, there is something here for everyone in the family, no matter how picky they are. There is a sidewalk patio if the weather is warm, or dine inside in a welcoming dining room surrounded by amazing murals and Halloween decor. After – take a short walk to the charming main street in Tarrytown where there is a toy store, additional restaurants, and local stores.
Horsefeathers. 94 North Broadway, Tarrytown, NY. Website and menu HERE.
