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Tarrytown Travel Guide

Halloween Country: Tarrytown and Sleepy Hollow, New York

By Lisa Van Allen

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If there’s one quintessential American ghost story, a good case could be made for Washington Irving’s “The Legend of Sleepy Hollow.” Never mind how the original Headless Horseman story has morphed over the years from cute and spooky into occult and gory—as in Fox’s series Sleepy Hollow. The story is as integral as any to Halloween, so there’s no better place to celebrate the holiday than Sleepy Hollow and Tarrytown, New York, the towns where the legend takes place.

A quick train ride brings visitors twenty-five miles outside of New York City, where this bustling suburban grid sits on the banks of the wide, blue Tappan Zee. Come autumn, the area’s historic estates don their Devil’s Night best and put on countless Halloween celebrations for every taste.

Any visit to Tarrytown and Sleepy Hollow should start with a trip to see Washington Irving’s quaint, ivy-choked cottage called Sunnyside—after all, he’s the guy who started it all. Keep your eyes peeled and you just might see his ghost peering through a dark window, possibly pining for his lost love.

Lyndhurst Estate

From there head to nearby Lyndhurst, the estate of nineteenth-century railroad baron Jay Gould. Lyndhurst has been the setting for many a spooky movie and TV show, including House of Dark Shadows, a staple for fans of vampire horror. Even if you’re not into this year’s seaonal offering, “Jay Ghoul’s House of Curiosities: Lyndhurst, The Disenchanted Castle,” the estate’s architecture alone is worth the price of admission, as the mansion is regarded as one of the best examples of Gothic Revival in the U.S. Notably, the estate is really the only venue in the area that offers daytime Halloween tours, which are a bit less spooky than the nighttime offerings.

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Headless Horseman Bridge

If you’ve only got a couple hours to kill, no Halloween adventure into Headless Horseman country would be complete without a visit to the Old Dutch Church and the adjoining Sleepy Hollow Cemetery. There, the Headless Horseman rose from Washington Irving’s imagination and famously chased Ichabod Crane through the haunted glen. There are tours for every interest—from nighttime lantern tours that conjure real-life stories of murder and madness to daytime perambulations that focus on Irving and the Sleepy Hollow legend. While you’re there, try to attend an event inside the Old Dutch Church. Built in the late seventeenth century, the quaint interior offers no electricity or heat, just candles and a stove—perfect for master storyteller Jonathan Kruk’s colorful rendition of “The Legend of Sleepy Hollow.”

With so much to do, you’ll have to keep your energy up. The good news is there are lots of places to eat and drink. For a local haunt, hop on line for a gyro at Lefteris on Broadway. If beer is your thing, you’ll love the huge selection and polished wood bar at The Bridgeview Tavern.

Blue Hill at Stone Barns

For a luxurious dinner you’ll never forget, head just outside Sleepy Hollow to Blue Hill at Stone Barns, an elegant farm-to-table restaurant set in the heart of an environmentally progressive, working farm. There, massive stone structures inspired by Normandy folk architecture will win you over even before you sit down to eat. You can also take advantage of the fabulous Blue Hill Café during the day. But don’t expect a table: just stake a claim on a picnic bench and chat up some locals. If you time it right, the sky will be blue, the October air sweet and crisp—and you’ll eat your gourmet lunch out of a brown paper box, surrounded by the fields where your kale and squash were growing not too long ago.

Philipsburg Manor

Finally, if you’ve spent a fair amount of your time in weatherworn graveyards or at haunted houses like The Horseman’s Hollow at Philipsburg Manor, you might need a moment to reflect. In that case, go seek a moment of solitude at one of my favorite but perhaps less visited spots in the area: Union Church of Pocantico Hills. For a few bucks, you can sit in one of the pews, ponder infinity, and gaze on a poignant collection of stained glass windows by Marc Chagall—not to mention Henri Matisse’s very last work of art.

Or, just hunt down some more Halloween—because there’s lots more to be had. Go get shivers up your spine gazing on the 5,000+ art-carved pumpkins at The Great Jack O’Lantern Blaze. Go on a hayride. Go sip hot apple cider and watch a parade. You might not get to do everything that Tarrytown and Sleepy Hollow have to offer in one weekend—but it will be fun trying!


Lisa Van Allen is the author of The Wishing Thread (Ballantine), a story of magic, sisterhood, knitting, and folklore in Tarrytown and Sleepy Hollow.

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