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Halloween in Sleepy Hollow

by Irvina Lew

Oct 14, 2019

Westchester County Tourism & Film

Destinations / North America

There are many Halloween-happenings in and near Sleepy Hollow, a historic Westchester County neighborhood located on the east bank of the Hudson River about 25 miles north of Manhattan. Halloween is such a major celebration in Sleepy Hollow that it is considered one of the “most haunted places in the world.” The following activities will entice, enchant and spook you … and your children. (Most are recommended for ages 10 and older).


The Legend of Sleepy Hollow

It’s been 200 years since Washington Irving wrote “The Legend of Sleepy Hollow,”  a short story about Ichabod Crane and the Headless Horseman. Irving, who lived at Sunnyside (1839–1859) in a part of Tarrytown now called Irvington, and is buried nearby in Sleepy Hollow cemetery, is himself a local legend. This season, the village will celebrate the anniversary within the Old Dutch Church through Nov. 3, with master storytellers repeating the classic tale accompanied by spooky organ music.


Legend of Sleepy Hollow at the Old Dutch Church in Sleepy Hollow. Photo: Westchester County Tourism & Film, by Tom Nycz


The Sleepy Hollow Experience

The Sleepy Hollow Experience, an outdoor theatrical, musically accompanied walking-tour version of the ghost story takes place at Sunnyside, where Washington Irving lived. There are seasonal drinks and tasty treats (but no seats) for this performance, sold out for seven years while touring the country.


Horseman’s Hollow

Horseman’s Hollow will also return for 15 terrifying evenings throughout October, when visitors can tour a transformed and fearsome landscape on the grounds of The Philipsburg Manor House (c. 1693), a National Historic Landmark since 1961. The scary scenes are portrayed by professional actors as vampires, witches, undead soldiers, ghouls, ghosts and the Headless Horseman.


Horseman’s Hollow at Philipsburgh Manor in Sleepy Hollow. Photo: Westchester County Tourism & Film, by Tom Nycz


The Great Jack O’Lantern Blaze

About ten miles up river, The Great Jack O’Lantern Blaze in Croton-on-Hudson is considered one of the most unique and electrifying Halloween experiences. The magnificent display of more than 7,000 illuminated jack o’lanterns — hand-carved by 1,000 volunteers — fills Van Cortland Manor’s historic 18th-century grounds through Nov. 30. Check out the new Museum of Pumpkin Art, a pumpkin windmill, carousel and a 25-foot Statue of Liberty. Historic Hudson Valley recommends that to get the most out of a short visit, schedule evening performances for all three, one after another.


Halloween Parade

The 18th annual Tarrytown Halloween Parade takes place Oct. 26.


Haunted Hayrides

The village hosts haunted hayrides Oct. 25 and 26.


Cemetery Tours

And, there are kerosene lantern tours and day tours of the Sleepy Hollow Cemetery.


The Legend of Sleepy Hollow, the Musical

The Legend of Sleepy Hollow, the musical by William Allen Jones, made its debut in 2018 and will play at the Irvington Theater Oct. 19, 20, 24, 25, 26.


And, throughout the year…

Sleepy Hollow fascinates from May to November; there are timed tours of Philipsburg Manor House, where the interior is decorated with 17th- and 18th-century period furnishings. Costumed interpreters re-enact life in pre-Revolutionary times, when the family’s 23 household slaves did the chores. (The Philips family transported slaves from Africa and supported the British. Loyalists seized their home in 1789, after the Revolution; later, the British compensated the family.) Kykuit, in Sleepy Hollow — where four generations of the Rockefeller family made their home —  is listed as a historic site on the National Trust for Historic Preservation. It’s a historic mansion to visit, with elegant sculpture-studded gardens, an amazing art collection and incredible river views. In 1921, John D. Rockefeller built the beautiful stone structure — the Union Church of Pocantico Hills — where they worshipped and for which he asked Henri Matisse to design the rose window. His children commissioned Marc Chagall to create nine stained glass windows in his honor, including the “Good Samaritan.”

Sleep Hollow Cemetery tour. Photo: Westchester County Tourism & Film


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