Sleepy Hollow New York — The Best Things To Do This Fall

There aren’t many towns more synonymous with Halloween than Sleepy Hollow New York. Made famous by Washington Irving’s classic short story, “The Legend of Sleepy Hollow,” Sleepy Hollow continues to live up to its namesake as a town steeped in horror and mystery. An idyllic community nestled along the Hudson River, Sleepy Hollow transforms itself into a haven of Halloween attractions at the beginning of every fall season.

Fun Things To Do in Sleepy Hollow New York

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With yearly events and one-of-a-kind attractions you won’t find anywhere else, Sleepy Hollow rivals the likes of Salem or New Orleans in terms of Halloween-related activities, delighting travelers from across the country. From their annual haunted hayride to historical tours through local points of interest, here are some of the best activities we recommend doing in Sleepy Hollow this autumn.

The Great Jack O’Lantern Blaze

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One of the biggest recurring events that draws visitors to Sleepy Hollow is the town’s annual Jack O’Lantern Show, affectionately known as “The Great Jack O’Lantern Blaze.” Sprawling in front of Sleepy Hollow’s opulent 18th mansion houses, The Great Jack O’Lantern Blaze features over 7,000 hand-carved pumpkins, each adorned with distinct designs (humorous, scary, and wonderfully creative). Along the way, guests will hear a unique musical soundtrack made specifically for the show and get a glimpse of a brand-new pumpkin Ferris wheel and a gourd-themed circus sideshow.

As memorable an attraction as it is, The Great Jack O’ Lantern requires visitors to purchase their tickets online ahead of time. Given the high volume of traffic the event receives, tickets are not sold anywhere on-site.

Home of The ‘Legend’

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In 1820, American author Washington Irving helped put Sleepy Hollow on the map with his influential short story, “The Legend of Sleepy Hollow.” A timeless tall tale punctuated by gothic horror and suspense, Irving used his intimate knowledge of nearby Tarrytown to inform the setting of “Sleepy Hollow,” later settling down in the town in 1835.

Today, visitors to Sleepy Hollow can still see the riverside cottage Irving retired to courtesy of the Home of the ‘Legend’ tour. In this instructive and educational show, guests can tour the grounds of Irving’s Sunnyside estate, learning about the author’s life and the significant effect “Sleepy Hollow” had on literature and pop culture.

The Annual Haunted Hayride

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A decent number of people have probably gone on a haunted hayride at some point. However, few people can claim to have retraced Ichabod Crane’s flight from the Headless Horseman – something travelers can achieve through Sleepy Hollow’s Haunted Hayride.

Clattering through the heart of Sleepy Hollow, guests follow in Ichabod’s footsteps past the Old Dutch Church, heading into the town’s sprawling cemetery grounds. As they wind their way through these historic grounds, passengers encounter all kinds of demonic figures and horrific sights, perhaps even bumping into the notorious Horseman himself.

Octagon House

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One of the most unique houses within Sleepy Hollow is the famous Octagon House. Constructed in the 1860s, it’s one of the few houses in the U.S. to boast an octagonal design, utilizing a classical temple’s design for influence. With events taking place throughout the season, guests are able to take a guided tour through the house – learning about its distinct shape and the reason for its odd design – or enjoy a picturesque tour past some of the estate’s lush vegetation.

In September and October, the Octagon House also features a more in-theme Myths and Mysteries Tour, with guides informing visitors of the mansion’s alleged connections to the spiritual world. At certain points in the season, the house also features the interactive tour, “The Lady in White,” in which guests come face-to-face with a mysterious spirit said to haunt the halls of the Octagon House.


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Constructed in the early years of the 20th century, Kykuit was designed as the familial home for the famed Rockefellers, serving as the family’s residence for four generations. Spread over 3,400 acres, Kykuit now offers guided tours through Rockefeller's historic estate, learning first-hand what it might have been like to live like a Gilded Age millionaire.

Open on an almost year-round basis, Kykuit may be low on seasonal scares, but it nevertheless makes for an interesting place to explore. The estate’s classic tours run for an impressive two and a half hours, with the three-hour grand tour allowing guests extended time in the house’s gardens and prestigious art gallery.

Sleepy Hollow Cemetery Tours

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Cemetery tours might be a fairly niche activity, but in retrospect, it’s difficult to find a cemetery more worth seeing than Sleepy Hollow’s. Divided into several different kinds of tours, each experience visiting Sleepy Hollow’s Cemetery makes for an engrossing activity, featuring stories that are as historically interesting as they are potentially spine-chilling.

In “The Original Knickerbocker: Washington Irving & The Legend of Sleepy Hollow,” visitors learn about the relevance of Washington Irving and his most famous short story. In the “Classic Daytime Tour,” guests saunter past some of the cemetery’s most famous graves, including the final resting places of Andrew Carnegie and William Rockefeller, among many others. In “The Murder and Mayhem Tour,” visitors take a guided lantern-lit journey through the cemetery grounds, hearing twisted tales of murder, misfortune, and tragedy from their knowledgeable tour guides.

The Legend Cirque

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Anyone heading to Sleepy Hollow should be at least partially familiar with “The Legend of Sleepy Hollow.” Whether familiar with the age-old tale or not, visitors can always enjoy a unique take on Irving’s short story thanks to theatrical productions like The Legend Cirque.

In this hair-raising adaptation of Irving’s story, guests witness the gravity-defying antics of Ichabod Crane, his love Katrina, and his rival Brom as they navigate a perilous love triangle, leading to Ichabod’s climactic encounter with the enigmatic Headless Horseman. An excellent and refreshing spin on a centuries-old urban myth, The Legend Cirque is a must for anyone partial to Cirque du Soleil-style performances.

The Horseman: Terror Lives in Chaos

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A brand-new event debuting this fall, The Horseman: Terror Lives in Chaos, offers a terrifying attraction fit for every horror buff venturing to Sleepy Hollow. Created by the celebrated New York team artistic Psycho Clan, Terror Lives in Chaos utilizes a classic haunted house set-up, albeit with far more frights and scares than the local haunted hayride held nearby.

Carefully designed with an atmospheric emphasis on horror and suspense, Terror Lives in Chaos takes visitors on a frightening journey through a strange hospital while the Four Horsemen of the Apocalypse chase after anyone who steps inside. Tickets are available online in advance or via walk-up purchases, with the event running from the beginning of October into early November.