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I’m driving through the Philipse Manor neighborhood in Sleepy Hollow, N.Y., to collect my daughter from her friend’s house when a blood-curdling shriek meets my ears. Across the street, a large black horse paws the ground, agitated — yet the animal’s rider remains eerily still. The cloaked horseman is missing a very important appendage.
As the setting for Washington Irving’s famous legend, Sleepy Hollow has become one of the most iconic Halloween destinations in the country, and the headless Hessian soldier appears everywhere from local parades to the high school’s homecoming game. I’ve lived in neighboring Tarrytown for 20 years, but even I get the shivers come October — catching a glimpse of the decapitated spirit on horseback never gets old.
Overlooking the majestic Hudson, just 20 miles north of New York City and near the Tappan Zee Bridge, Sleepy Hollow and the surrounding towns host myriad daytime and evening Halloween activities — from the whimsical to the downright terrifying — offering visitors and locals alike multiple ways to savor the spooky season and see the legend come to life.
Kick things off a few miles south at Sunnyside, Irving’s riverfront home, which he described as “a little old-fashioned stone mansion, all made up of gable-ends, and as full of angles and corners as an old cocked hat.” The author spent the last years of his life in this enchanting storybook cottage that even had its own railway station on the banks of the Hudson. Perfect for those with a lower fright threshold, autumn tours of Sunnyside introduce Irving’s life and legacy while revealing inspirations behind the prolific writer’s most famous tale. Children will love watching a shadow puppet performance of “The Legend of Sleepy Hollow” and joining a scavenger hunt throughout the bucolic grounds.
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Right in the heart of Sleepy Hollow Village, the Old Dutch Church, built in 1697, remains one of the oldest in the country, and the graves of the locals who influenced Irving’s characters can be found within its historic burying grounds. You won't find the final resting places of Ichabod Crane or Abraham “Brom Bones” VanBrunt among the tilting 18th-century markers, but you will come across the grave of Eleanor Van Tassel Brush, whom Irving purportedly modeled Katrina Van Tassel, the legend’s coquettish debutante, after. Eleanor’s aunt, Catriena Ecker Van Tassel, is also buried here.
Come nightfall, master Hudson Valley storyteller Jonathan Kruk regales audiences with theatrical performances of Irving’s Legend accompanied by dramatic, live organ music and the flicker of candlelight.
Daytime visitors can wander nearby Sleepy Hollow Cemetery’s foliage-filled landscape that's complete with elaborate mausoleums and haunting tombstones. Irving himself rests here along with other notable figures like Andrew Carnegie, Elizabeth Arden, Samuel Gompers and William Rockefeller. Evening lantern tours provide an especially hearty dose of All Hallows spirit. While in the Washington Irving Chapel, local author-actor David Neilsen offers a spine-tingling reading series featuring the short works of Irving, Edgar Allan Poe and others throughout the season.
At the historic restoration of Philipsburg Manor, evenings find thrill seekers winding down a lantern-lit path to a ghostly hamlet haunted by the headless Hessian himself. The macabre of every variety — gory ghouls, a harrowing corn maze, tormented villagers gone mad — accompanies the journey to the final destination, Ichabod Crane’s schoolhouse, where visitors may meet the same fabled fate as Irving’s lanky schoolmaster.
Far less creepy and new for this season are evening screenings of an original silent film titled The Unsilent Picture, inspired by Irving’s curious tale, “The Adventure of the Mysterious Picture.” Starring Bill Irwin, live musicians and sound effects created by an in-person Foley artist bring a dynamic energy to the event.
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What may just be the best-loved Halloween spectacle in the area takes place a few miles north in Croton-on-Hudson at Van Cortlandt Manor, home of the Great Jack-O’-Lantern Blaze. What began as a local celebration in 2005 now welcomes close to 170,000 guests each season. More than 7,000 hand-carved pumpkins illuminate the nine-acre historic homestead in elaborately-themed displays — think giant spider webs, a field of scarecrows, a 25-foot-tall Statue of Liberty, and even a fully-functioning jack-o’-lantern carousel. With dazzling lighting and an original soundtrack — and even signature craft beers made by the local Captain Lawrence Brewing Co. — the squash spectacular is a glowing way to close out a legendary autumn journey.
Driving's easiest, but if you're coming from New York City without a car, you can catch a train at Grand Central Station to Tarrytown — about a 40-minute trip — then it's a short walk to Main Street.
Where to stay:
Castle Hotel and Spa
A member of the Small Luxury Hotels of the World organization, this majestic property in Tarrytown overlooking the Hudson River is home to 31 elegant guestrooms, a sumptuous spa and Equus, an award-winning restaurant.
Just up the hill from Washington Irving’s Sunnyside, the 19th-century Tarrytown House features 212 plush rooms and sweeping Hudson River views from its landscaped grounds.
Both properties offer special Halloween packages that include two VIP tickets to the Great Jack-O’-Lantern Blaze and breakfast.
Where to eat:
This quintessential Irish pub, a short walk from Philipsburg Manor, has been a Sleepy Hollow institution for almost 20 years and serves hearty fare such as shepherd’s pie, homemade meat loaf and what may just be the best burger in town.
Bridge View Tavern
Tap handles from a prolific selection of craft brews adorn the rafters in this cozy Sleepy Hollow tavern with views of the historic Sleepy Hollow Lighthouse. Menu favorites include succulent barbecue pulled-pork sandwiches and Dr. Pepper-braised short ribs.
Gourmet market meets upscale eatery at this vibrant gastronomical hub on Tarrytown’s Main Street. Diners snack on cured olives, cheeses and charcuterie while perusing an eclectic mix of savory selections such as beer-broth mussels, grilled figs with goat cheese, and seared scallops over risotto.
Sweet Grass Grill
Local Hudson Valley farms help dictate the seasonally rotating menu at this inviting field-to-fork restaurant in the heart of Tarrytown. Draft brews, craft cocktails and a great wine list accompany miso-glazed salmon and wild mushroom fettuccine.