Going Places, Near & Far…‘Legend of Sleepy Hollow’ Halloween Events – Ghouls & All – Return to Historic Hudson Valley

The Island Now

Washington Irving’s macabre tale, “The Legend of Sleepy Hollow,” is the inspiration for Horseman’s Hollow, a spectacularly produced interactive Halloween haunted attraction at the colonial-era Philipsburg Manor in Sleepy Hollow, N.Y.
It is one of a series of Historic Hudson Valley’s Halloween season spectacular events taking place over an unprecedented 32 nights. They are the largest Halloween events in the tri-state area and are expected to draw more than 150,000 visitors to Sleepy Hollow Country. They take place in several Historic Hudson Valley venues, each one an important attraction.
Washington Irving’s macabre tale The Legend of Sleepy Hollow inspires Horseman’s Hollow, an interactive haunted attraction taking place over 14 nights at Philipsburg Manor in Sleepy Hollow, an estate that dates back to colonial times. But for Halloween, it is stocked with professional actors and state-of-the-art special effects and lighting. Take note: Horseman’s Hollow has a high fear factor, which is why it is so popular with teenagers. (Recommended for ages 10 and up.)
Irving’s ‘Legend,’ recommended for ages 10 and up, brings the master storyteller Jonathan Kruk into the historic, candlelit interior of Sleepy Hollow’s circa-1685 Old Dutch Church, where for 14 afternoons and evenings he offers a dramatic re-telling of The Legend of Sleepy Hollow accompanied by live organ music.
The Legend Behind the ‘Legend’ is a daytime experience at Washington Irving’s Sunnyside homestead in Tarrytown, N.Y., that highlights the author of the famous story.
And continuing for a record 32 selected evenings through Nov. 13, The Great Jack O’ Lantern Blaze® is the Hudson Valley’s biggest all-ages Halloween extravaganza. A small team of artists comes together to carve more than 7,000 jacks, many fused together in elaborate constructions such as life-size dinosaurs and eight-foot-tall working jack-o’lanterns-in-the-box, all lit up throughout the wooded walkways, orchards, and gardens of historic Van Cortlandt Manor in Croton-on-Hudson, N.Y.
Headless Horseman Rides Again
Philipsburg Manor, is but a few miles up the road from Washington Irving’s homestead at Sunnyside and, legend has it, is the setting for his classic story. The village, which was once known as North Tarrytown, actually changed its name to Sleepy Hollow in 1996.
But here at the 350-year old Philipsburg Manor, one of the Historic Hudson Valley historic sites, you can easily imagine the “Legend of Sleepy Hollow” as Irving saw it in his mind.
Now in its 7th year, Horseman’s Hollow, which welcomed more than 30,000 visitors last year, is a haunted experience in the heart of Sleepy Hollow that takes the tale of The Legend of Sleepy Hollow to its darkest extremes. Historic Philipsburg Manor transforms into a terrifying landscape ruled by the undead, the evil, and the insane, all serving the Headless Horseman himself.
For 14 nights, historic Philipsburg Manor transforms into a terrifying landscape ruled by the undead, the evil, and the insane, all serving the Headless Horseman himself.
The 300-year old manor house, barn and gristmill of the Philipses, a family of Anglo-Dutch merchants who owned the 50,000 acre- estate, become the sets and the backdrop for the really, really ghoulish hauntings by colonial spirits.
Haunted house professional Lance Hallowell is back this year to lead a crew of award-winning makeup and costume designers and a 45-member-strong cast of experienced actors to create an immersive, interactive, pleasantly terrifying experience, with state-of-the-spooky-art special effects.
Custom built set pieces and period-correct costumes help orient the experience in Philipsburg Manor’s traditional time period of the mid-1700s.
What is best about Horseman’s Hollow is the sheer number (and talent) of the live spirits – they are very considerate, too – they seem to know just how much to terrify you (though really squeamish and young children should not come). I have found that if the ghouls sense you are easily frightened (like me), they tend to take down a notch their scare factor (I basically announce that I am easily frightened as I enter one of the venues).
But the professional actors and state-of-the-art special effects, contributes to a high fear factor (it’s recommended for ages 10 and up and is not for the squeamish and you need to take heed of the warning: This event is NOT suitable for adults who are claustrophobic, have heart or respiratory conditions, are prone to seizures, or have other chronic health conditions.)
As we start our experience, walking up a dirt path that rings the pond, a faceless colonial escorts us for a time, then goes into the trees to surprise a group of teenagers who are following behind. With each step through the woods, you leave the modern world behind and suspend disbelief.
Timed tickets mean that it isn’t overcrowded (safety in numbers?) – but as we walk through (guided by helpful spirits with lanterns who lead us to the next haunted house), we hear the screams of a pack of teenage girls in the distant dark. It adds to the atmosphere.
Look carefully in the deepest, darkest shadow, and there is the Headless Horseman himself, astride his steed, standing quietly as if taking in the scene or simply delighting in the terror of recognition as the clueless passerby realizes who is lurking in the dark.
Horseman’s Hollow dates are Oct. 7-9, 14-16, 21-23, 27-31. Online tickets are $20 ($25 on Saturdays).  Fast Track, for a $15 per ticket upgrade, lets visitors skip the line in their timeslot. Historic Hudson Valley members receive a$5 per ticket discount.
Philipsburg Manor is at 381 North Broadway (Route 9) in Sleepy Hollow. (There is a parking field.)
Great Jack O’Lantern Blaze
The Great Jack O’ Lantern Blaze, which drew more than 130,000 visitors last year, features more than 7,000 illuminated, individually hand-carved jack o’ lanterns. Elaborate single-pumpkin carvings and huge multi-jack o’lantern constructions are professionally lit throughout the landscape of Van Cortlandt Manor in various themed areas.
Favorite installations such as Jurassic Park and the giant spider web are joined this year by new creations including a plus-sized Pumpkin Planetarium, a Pumpkin Zee Bridge, and a brand-new herd of pint-sized dinosaurs all made of jack o’lanterns.
Creative Director Michael Natiello leads a small team of Historic Hudson Valley staff and local artists who carve. In addition, more than 2,000 volunteers help scoop and light the pumpkins. You can watch Blaze artists carving on site during the event.
Café Blazé, by Geordane’s of Irvington, offers culinary treats including soup, veggie chili, muffins, pumpkin cookies, and cider. The Great Jack O’ Lantern Blaze Shop has a full bounty of Blaze-specific merchandise including hats, notepads, games, T-shirts, magnets, caps, mugs, and jewelry.
New music this year created by professional musician, radio personality, and Halloween fanatic Richard Christy will augment the visitor experience. The new tracks as well as music from Christy’s Blaze: The Soundtrack Volume I & II play throughout the event. (Soundtrack Volume II is available as a CD at the event and both volumes are available as digital downloads and streams from iTunes, Amazon, and Google Play.)
Blaze dates are Sept. 30, Oct. 1-2, 7-10, 13-16, 19-31, Nov. 3-6, 10-13. Online tickets are $20 for adults ($25 on Saturdays), $16 for children 3-17 ($20 on Saturdays), and free for children under 3 and Historic Hudson Valley members.
Van Cortlandt Manor is at 525South Riverside Avenue, just off Route 9 in Croton-on-Hudson (A parking field is on site).
Irving’s ‘Legend’
Master storyteller Jonathan Krukoffers a dramatic re-telling of Washington Irving’s classic tale, The Legend of Sleepy Hollow, featuring the Headless Horseman, Ichabod Crane, Brom Bones, and Katrina Van Tassel. Flavored with live spooky organ music by Jim Keyes, Kruk’s storytelling takes place in the historic, candlelit setting of the Old Dutch Church in Sleepy Hollow. The circa-1685 stone church is across the street from Philipsburg Manor, where visitors will park. Performances last about 45 minutes.
Irving’s ‘Legend’ dates are Oct. 7-9, 14-16, 21-23, 27-31. Seating is very limited and there are three performances each evening. Online tickets are $25 for adults, $20 for children under 18. Historic Hudson Valley members receive a $5 per ticket discount.
Legend Behind the ‘Legend’
Sunnyside, the home of Washington Irving, celebrates its connection to Irving’s classic tale, The Legend of Sleepy Hollow, at this family friendly daytime event. The Legend Behind the ‘Legend includes tours of Irving’s home – a colorful blend of architectural styles – which showcase numerous objects from HHV’s collection related to Irving’s famous story. Visitors can also enjoy a shadow puppet performance of The Legend of Sleepy Hollow and experience one of Irving’s spooky tales on a walk through the woods. Sunnyside is on West Sunnyside Lane, off Route 9 in Tarrytown.
Legend Behind the ‘Legend’ dates are Oct. 1-2, 8-9, 15-16, 22-23, 29-30. Online tickets are $16 for adults, $12 for seniors, $8 for children 3-17, and free for those under 3 and Historic Hudson Valley members.
All events are held rain or shine. Proceeds support Historic Hudson Valley, the Tarrytown-based private, non-profit educational organization that owns and operates the historic sitesthat host these events.
Because of the popularity of these events, it is essential to purchase tickets in advance.
Buy tickets online at www.hudsonvalley.org or by calling 914-366-6900 ($2 per ticket surcharge for phone orders and for tickets purchased onsite, if available).


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