Spending the night in Sleepy Hollow
This real-life setting for the legendary story of the headless horseman provides a surprisingly relaxing holiday destination.
For almost two centuries, horror fans have been spooked by the story of a headless horseman who terrorised a village in New York. Washington Irving’s 1840 novel, The Legend of Sleepy Hollow, inspired a 1949 Walt Disney animation, narrated by Bing Crosby, as well as Tim Burton’s 1999 film, Sleepy Hollow, starring Johnny Depp and Christina Ricci, and a television series of the same name (available on Disney).
The terrifying tale is set in a real-life town about 50km north of Manhattan. No longer the isolated farming community depicted in fiction, Sleepy Hollow is a dream for anyone tired of the city. Snuggled on the east bank of the Hudson River, this quiet nook embraces its creepy connotations, especially in the weeks before and after Halloween.
Near the Sleepy Hollow Bridge is a sculpture of the infamous horseman, opposite the Dutch Reform Church where Irving’s protagonist Ichabod Crane fled to escape him. Behind this 17th-century church is Sleepy Hollow Cemetery, where Irving is buried.
What to do in Sleepy Hollow
Not for the faint-hearted, night tours are led by lantern on weekends (daily in October). The 36ha grounds contain the graves of many other writers, actors, Civil War soldiers and local entrepreneurs. The largest mausoleums belong to oil tycoon William Rockefeller, cosmetics queen Elizabeth Arden and Walter Chrysler, founder of the automobile company.
A month-long festival, Sleepy Hollow Halloween, is celebrated with scary events, street fairs, parades, a marathon of runners dressed in costumes and, of course, a “decapitated” bloke
riding around on a horse.
Hair-raising activities include the Haunted Hayride on a hay wagon through the streets and into the woods, and the new Spirits of Sleepy Hollow Country, where illusionists perform tricks and conjurings as they attempt to communicate with ghosts.
A more family-friendly tour is offered at Lyndhurst Mansion, one of America’s best-preserved examples of Gothic Revival architecture. Launched last year, the Lyndhurst After Dark tour allows visitors to experience the mansion decorated in the spirit of the season, with displays of special items relating to superstitions of the age.
The land was originally the hunting grounds of the indigenous Lenape/Munsee tribe, the first inhabitants of the Hudson Valley, before it was cleared by European settlers. Expanding from a country villa to a park-like estate, Lyndhurst was shaped over the 19th century by three wealthy families: the Pauldings, the Merritts and the Goulds. During this period, Romanticism dominated the arts, which is evident in the vast collection of paintings and furniture left behind by the previous owners.
Separate buildings house one of the oldest regulation bowling alleys in the US, the remains of a Lord & Burnham greenhouse, a restored laundry and servants’ cottage, and an indoor swimming pool built in the style of a Roman bath. The former carriage house, which contained stables and a coal shed, has been converted into an art gallery and gift shop. A year-round tour covers the parlour, art gallery and dining room.
Lyndhurst has been used for moody scenes in several movies including Winter’s Tale and House of Dark Shadows, whose vampire also haunted Sleepy Hollow Cemetery.
Ironically, Sleepy Hollow wasn’t filmed anywhere nearby; it was largely shot in a studio in England.
The origins of Sleepy Hollow date back to the establishment of Philipsburg Manor, a farming and milling centre founded by carpenter Frederick Philipse, who switched his allegiance to the Crown when the British evicted the Dutch from the colony of New Netherland and renamed it New York.
In 1750, it was home to several hundred farmers and two dozen African slaves. An on site museum shows how Dutch, African and Native American cultures became entwined at this colonial outpost.
I spend a month holed up in Sleepy Hollow, as a peaceful alternative to New York City. Staying in a three-bedroom house arranged via a home-exchange website, I relish the relaxing atmosphere and riverside location. I go for morning walks along the Hudson, swim alone in hidden coves, and enjoy the waterfront pubs and restaurants.
A friend with a boat picks me up from the Shattemuc Yacht Club and takes me sailing upstate. Kayak tours and stand-up paddle-board classes are also available in summer.
For nature-loving on land, there are plenty of walking trails and wildlife. Rockefeller State Park has a network of carriage roads through the woodlands, where I spot deer and hawks on my afternoon strolls.
Best for sunset is Rockwood Hall’s fields, perfect for picnics. A 20-minute drive, North County Trailway is an old railroad track that has been turned into a bike path stretching all the way down to the Bronx. Teatown Preserve has paths around lakes and a centre for rescue animals, from ferrets to bald eagles.
Where to eat in Sleepy Hollow
The dining scene is limited but lovely. Hudson Farmer and the Fish, situated on the Riverwalk, receives daily deliveries from the owners’ farm and a local seafood supplier. An open kitchen with a chef’s counter, outdoor tables and a private room enhance the experience. In nearby Tarrytown is the farm-to-table RiverMarket Bar & Kitchen, and inside an 1840s mansion is Goosefeather, serving Cantonese cuisine.
Top picks for a drink include the rooftop bar at Hudson Anchor, the beer garden at Bridge View Tavern, and two pubs with live music, The Sailhouse and Barley on the Hudson, both in Tarrytown. Within walking distance, Tarrytown was described by Irving as “a retreat whither I might steal from the world and its distractions and dream quietly away.”
My favourite spot is 3 Westerly Bar and Grill in Ossining for its weekday happy hour ($US$8 wine, US$10 cocktails and US$1.25 oysters). A seven-minute walk leads to The Boathouse, which has prime position on the wharf and an adorable “boat bar” with stools perched around a 22ft Catalina. At any of these venues, there is never a need for a reservation to score a seat with river views.
Westchester County runs the public buses, which are free of charge in summer, so I explore every day without a car. Along the routes from Sleepy Hollow are stops in Tarrytown, Ossining, Katonah, Mount Kisco and the shopping destination of White Plains for a fashion spree at Bloomingdale’s, Nordstrom or Neiman Marcus.
Where to stay in Sleepy Hollow
Although Sleepy Hollow is an easy day trip from New York, it’s worth staying longer. A time-honoured option is the 31-room Castle Hotel & Spa in Tarrytown. It was built in 1897 as a home for the family of General Howard Carroll, who became a playwright and a political correspondent for The New York Times. Constructed in the style of Norman fortifications, Carrollcliffe (as it was called) hosted notable dinner guests such as Wall Street financier JP Morgan, industrialist Andrew Carnegie, foreign dignitaries and ambassadors.
Sold in 1941, it was turned into the headquarters of an investment advisory firm. During World War II, the roof and tower were used as an observation post by the Tarrytown Civil Defence to monitor air traffic.
In 1981, it was designated as a historic landmark to protect its external structure, before the latest owners transformed the interiors into a hotel.
Last year, the dining room reopened as an award-winning restaurant, Emerson & Ruth, named after the couple who bought the castle from General Carroll.
A five-course tasting menu is served among the rich mahogany panels and a towering stone fireplace.
Irving’s home has also been maintained as a tourist attraction with exhibits and tours. Fans can visit his whimsical house and gardens in the neighbouring namesake suburb, Irvington.
From May to November, guides in period costumes explain how he became America’s first internationally famous author, writing Rip Van Winkle as well as numerous essays, biographies and travelogues.
As Irving describes the character of Ichabod Crane: “Our man of letters, therefore, was peculiarly happy in the smiles of all the country damsels … sauntering, with a whole bevy of them, along the banks of the adjacent millpond; while the more bashful country bumpkins hung sheepishly back, envying his superior elegance and address”.
I find myself peculiarly happy sauntering solo in this peaceful and pretty corner of the Hudson Valley.
In the know
Sleepy Hollow is a 55-minute train ride from New York City’s Grand Central Station to Philipsburg Manor; a 38-minute express train stops at Tarrytown.
Lyndhurst Mansion reopens for tours in April.
Castle Hotel & Spa has extensive gardens, a fine-dining restaurant, bar, library, pool, gym and jogging track. Live music and tastings of wines and spirits are offered poolside on summer Fridays. Rooms from $US169 ($250) a night.
Louise Goldsbury travelled at her own expense.
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