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Sleepy Hollow’s Spirits: For Haunting and Savoring

“From the listless repose of the place, and the peculiar character of its inhabitants, who are descendants from the original Dutch settlers, this sequestered glen has long been known by the name of Sleepy Hollow ... A drowsy, dreamy influence seems to hang over the land, and to pervade the very atmosphere.”

- "The Legend of Sleepy Hollow"

The town of Sleepy Hollow was made famous by Washington Irving, when he published a short story entitled, “The Legend of Sleepy Hollow” in 1820. This iconic tale’s impact can still be felt in pop culture. The latest example is Fox’s critically acclaimed time-traveling conspiracy theory vehicle, “Sleepy Hollow,” which garnered 10.1 million viewers during its premiere on Sept. 16, the biggest opening night Fox has enjoyed in six years.

Buy "Legend of Sleepy Hollow" Book illustrated by New York maker Will Moses >>

Irving’s narrative was set in 1790 and relays the story of Ichabod Crane, a greedy and superstitious Connecticut schoolmaster, who is angling for the hand of the beautiful Katrina Van Tassel, the apple of her wealthy father’s eye. The town belle is simultaneously pursued by local resident Abraham “Brom Bones” Van Brunt. Hijinks ensue, culminating in Ichabod’s fateful encounter with a cloaked, headless horseback rider and his subsequent disappearance.

It is unclear from the story whether the run-in with the equestrian specter was a supernatural occurrence, or if Van Brunt and/or Van Tassel helped engineer the tragic ending. The intrigue of the conclusion’s ambiguity and the haunted tenor of the story long-ago secured “The Legend of Sleepy Hollow” a permanent place in the American literary canon, and has had an inestimable effect on generations of writers, filmmakers and Halloween enthusiasts everywhere.

In addition to the skillfully-crafted plot, Irving also managed to convey the essence of the town of Sleepy Hollow, which is a must-visit on any trip to the Hudson Valley. As expected, you will stumble upon the inevitable Irving kitsch, but there are also world-class gourmet restaurants, quirky hole-in-the-wall food joints, cool bars, a smattering of historical buildings to peek into and, more importantly, the other-worldly, mellow vibe of the town itself.


The bad news first: the bridge where Ichabod Crane met both the headless wonder and his own demise is no more; ditto the old Sleepy Hollow schoolhouse where Ichabod was schoolmaster. The good news: all of the other landmarks from the tale are in tact. Following the story’s plot, ride up the Albany Post Road (now named Broadway) at the site of the Van Tassel house, to Patriot’s Park (where the Headless Horseman was first seen), to the Old Dutch Church and graveyard (where the Horseman liked to rest between hauntings). Sleepy Hollow Cemetery has a fantastic, detailed travel guide (with addresses) that will delight serious horror aficionados.

Irving’s own residence, Sunnyside, is located in nearby Tarrytown. Originally a Dutch farmhouse, the home has been restored and is open for tours. Rates and hours vary season to season. While in Tarrytown, pay homage at Christ Episcopal Church, Irving’s longtime church and the location of his funeral in 1859. Irving’s favorite pew is marked for fans.


If you are suffering from Halloween horror fatigue, the Rockefeller State Park Preserve provides 1,600 serene acres of forest, meadows and broken stone roads that were created to maintain the historic and natural beauty inherent in undeveloped portions of the Hudson Valley.

125 Phelps Way, Pleasantville, NY 10570. (914) 631-1470.

Philipsburg Manor and Kykuit, the Rockefeller Estate in Sleepy Hollow, are grand examples of la vida loca, 18th century style. The manor has been restored to its state in 1750 and is presented as a colonial-era farming, milling and trading depot.

381 North Broadway, Sleepy Hollow, NY 10591. (914) 631-3992.

Lyndhurst is a gothic revival mansion sitting on 67 acres in Tarrytown. Designed by Alexander Jackson Davis in 1838, it also happens to be the site of the 1960s TV series “Dark Shadows.”

635 South Broadway, Tarrytown, NY 10591. (914) 631-4481.

The Union Church of Pocantico Hills boasts a stained glass window by Henri Matisse and nine others by Marc Chagall.

555 Bedford Road, Pocantico Hills, NY 10591. (914) 631-8200.


An entire day devoted to gluttony could be whiled away reveling in the area’s incredible variety of delectable dishes. For the deep-pocketed gourmand, the inimitable Dan Barber’s Blue Hill at Stone Barns in Pocantico Hills is a must and just a 5 minute drive from downtown Sleepy Hollow. Located within a year-round working farm and educational Center for Food and Agriculture, the food at this seasonal restaurant is fresh and delicious. Meals are served as a “succession of small plates” starting at $148 without wine pairings. For foodies with shallower wallets, the farm is free and accessible to gawkers, as is the Blue Hill Café, which is open for lunch and is much less expensive than the formal restaurant.

630 Bedford Road, Pocantico Hills, NY 10591. (914) 366-9600.

Los Andes Bakery boasts traditional Chilean pastries, plus meat, cheese and fish empanadas.

180 Valley Street, Sleepy Hollow, NY 10591. (914) 631-3256

J&G Deli is an Italian family affair, with classic Italian-American sandwiches, espresso and baked treats.

23 Beekman Avenue, Sleepy Hollow, NY 10591. (914) 332-5321.

Bridge View Tavern serves up comfort and pub food classics, plus 15 beers on tap, with an emphasis on local favorites like Captain Lawrence.

226 Beekman Avenue, Sleepy Hollow, NY 10591. (914) 332-0078.

Santorini Greek Restaurant dishes out the expected gyros and souvlaki, and also lesser-known Greek hits like saganaki (flambéed cheese) and loukaniko (Greek sausage).

175 Valley Street, Sleepy Hollow, NY 10591. (914) 631-4300.

If you want to get into the spirit without leaving home, there’s always the TV show, the movie or the story to escape to.

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