Get Spirited in Sleepy Hollow, New York
More than a legend, Halloweentown USA is a real place less than an hour from New York City — and there’s no better time to visit than right now.
It’s no tall tale that Halloween lingers for about three months in Sleepy Hollow, New York. Steeped in tradition and legendary lore, the village (and its underworld) are brought to life, September to November, during the spookiest time of year, as ghost- and goblin-chasers emerge from the shadows and descend upon the area for a good bone chilling paired with a solid lesson in history. Should you dare, here is everything you need to know and do when braving a Halloween season like no other.
Irving’s Legend
Sunnyside
If time allows only a mere a taste of the annual festivities, make haste to Sunnyside, the estate of Washington Irving, for an outdoor, over-the-top dramatic portrayal of The Legend of Sleepy Hollow by master storyteller Jonathan Kruk, complemented by haunting music, sound effects, and a guest appearance by none other than the Headless Horseman himself. A night for the books!
Friday to Sunday evenings (plus Columbus Day and Halloween) through November 3
Legend of Sleepy Hollow Discovery Walk
Philipsburg Manor
Those that fear the dark (no judgement here) can embark on illuminating guided day tours of the hidden corners of Philipsburg Manor, the gristmill that inspired Irving’s timeless tale. Make a true day of it with an immersive tour of the property proper, learning about the slaves who labored for the Philipse family during the 1750s.
Friday to Sunday afternoons through November 3
Spirits of Sleepy Hollow Country
Philipsburg Manor
Ride in for a night of chills and thrills with master illusionists Mark Clearview and Nick Wallace, who bend the mind with their quicker-than-the eye magic tricks and possess a knack for conjuring locally famous spirits (looking at you, Headless Horseman).
Friday to Saturday evenings and Sunday late afternoons through November 3
Twilight Village at Sleepy Hollow
Philipsburg Manor
New for 2024, this open-air village intends to dazzle and delight with fortune teller tales, creepily crooned tunes, seasonal sips and snacks, ghoulish gifts, and a rare oddity: photo ops with the Headless Horseman.
Friday to Saturday evenings and Sunday late afternoons through November 3
Hulda’s Night
Rockefeller State Park Preserve
Travel back in time deep into the raw woods for an immersive theater experience, as storytellers share spine-tingling tales of Hulda the Witch and other local legends, with only lanterns lighting the way.
Wednesday to Saturday evenings, October 16-26
Rock & Roll House of Horrors
Holy Cross Parish Hall
Good old fashioned jump scares and rip-roaring music await on this guided walk-through haunted house, which ends with a photo op with the Headless Horseman.
Friday to Sunday evenings, October 4 through November 2
Cemetery Tours
Sleepy Hollow Cemetery
Two-hour guided tours, day or night (kerosene lanterns lead the way after dark), allow visitors to soak up the sublime surrounds at this 175-year-old graveyard and offer homage at the final resting places of some of New York State’s most famous residents.
October to November; every night, October to November
Tarrytown
Tarrytown Halloween Parade
Main Street
Two decades strong, this well-attended annual procession steps off from Patriot’s Park (where The Legend of Sleepy Hollow‘s Ichabod Crane first spots the Headless Horseman) and marches south along Broadway, before arriving at Main Street for a block party of eerily epic proportions with live music, performers, and a chilling cameo by the aforementioned jockey sans noggin.
Tarrytown; October 26 (rain date: October 27)
Lyndhurst Gothic Harvest Market
Lyndhurst Mansion
In the grassy shadow of this towering Gilded Age manse, peruse the spooky and kooky oddities of Hudson Valley makers and crafters, pausing for tarot card readings, a seasonal nibble, and to ogle the roving vampire.
October 26-27, 10am-4pm
Lyndhurst After Dark
Lyndhurst Mansion
Stick around for nightfall when guests are welcomed inside the castle for candlelit guided tours that delve into the darker side of past inhabitants.
Thursday to Sunday evenings, October 17-27
Irvington
Myths and Mysteries of The Octagon House
Armour-Stiner Octagon House
Docent-led hour-long tours take only the bold on a journey back in time to discover the tales and unexplained events that have plagued the inhabitants of this National Historic Landmark, built in 1872 and revered for its one-of-a-kind architecture.
