Literary Pilgrimage: Sleepy Hollow, New York

October is the perfect month to visit Washington Irving's favorite town—and the setting for his spine tingling short story, The Legend of Sleepy Hollow.



Though New York State has tried to re-name Sleepy Hollow “Tarrytown,” readers everywhere know better: The picturesque hamlet will always be the home of Icabod Crane and the infamous Headless Horseman.

Luckily, not much has changed, and fans of the story can revisit several familiar locations in the sleepy hamlet, located just about an hour north of New York City on the Hudson River. The churchyard that inspired Irving is still there, as is his home, Sunnyside. You can even visit Washington Irving’s grave, located just behind the Old Dutch Church. And for those not so obsessed with the writing of Washington Irving, there’s the beautiful Lyndhurst Mansion and the Rockefeller Estate, Kykuit, both on the register of historical places. Downtown Sleepy Hollow is filled with quaint antique shops and great restaurants, and the foliage in autumn is absolutely stunning.

Be careful: You might love Sleepy Hollow so much that you may end up a permanent resident—like Washington Irving—in the sprawling Sleepy Hollow Cemetery.


The Old Dutch Church and Burial Ground

Washington Irving's Grave
Photo: Natalie Maynor / Flickr

Washington Irving loved the town of Sleepy Hollow so much that he chose to immortalize the entire village, including the Old Dutch Church, in his short story, “The Legend of Sleepy Hollow.” And even that wasn’t enough for posterity. Irving wrote in 1849 to his friend Gaylord Clark, the editor of Knickerbocker Magazine, that he would like to be buried in the churchyard. (He is, in fact, buried in its backyard, in what would eventually become the much larger Sleepy Hollow Cemetery.) Unbelievably, the church was already old by the time Irving had discovered its charms. Historians believe it was completed as early as 1685, meaning it was well-established in the community by the time of the American Revolution. Today, you can still visit the beautiful, small church and adjoining burial ground.

Headless Horseman Bridge

Headless Horseman Bridge
Photo: pixonomy / Flickr

Right before you reach the Old Dutch Church, you will have to walk or drive over a small creek. This bridge is the place where, in Washington Irving’s tale, the Headless Horseman chases Icabod Crane into town. Though the bridge has long since rotted away, and the makeup of downtown has changed to accommodate modern roads, most scholars agree after studying Irving’s text, that its original location was just before the old church.

“He affirmed that on returning one night from the neighboring village of Sing Sing, he had been overtaken by this midnight trooper; that he had offered to race with him for a bowl of punch, and should have won it too, for Daredevil beat the goblin horse all hollow, but just as they came to the church bridge, the Hessian bolted, and vanished in a flash of fire.”—from The Legend of Sleepy Hollow

Sleepy Hollow Cemetery

Sleepy Hollow Cemetery
Photo: Gary Lerude / Flickr

The much larger Sleepy Hollow Cemetery is the resting place to many famous bones, including Washington Irving, Andrew Carnegie, Elizabeth Arden, Brooke Astor, Walter Chrysler, John and William Rockefeller, and veterans of the Revolutionary War. Originally called “Tarrytown Cemetery,” the town posthumously honored Washington Irving’s request to change the name to “Sleepy Hollow Cemetery.” The incredibly large graveyard takes up most of town, and is well worth a walk-through. And if you’re interested in spending eternity in Sleepy Hollow, it is still an active burial ground.

Washington Irving’s Sunnyside

Washington Irving's Sunnyside
Photo: June Marie / Flickr

In 1835, Washington Irving purchased a small property in Sleepy Hollow which he called “Sunnyside.” He wrote to a friend, “It is a beautiful spot, capable of being made a little paradise.” He paid $1,800 for the house and would, over the years, make expansions to the property. The house became a tourist attraction even in Irving’s lifetime, as by then he had become internationally-renowned. Irving lived here until his death in 1859, and the Irving family continued to care for the house until 1945, at which point they sold it to the Rockefeller family, who made it an official historical site. If you are interested in the Rockefeller family, or pretty houses, their estate, Kykuit, is nearby.

Lyndhurst and Jay Gould’s House of Curiosities

Photo: Jeremiah Mercurio / Flickr

During the Halloween season, visitors of Jay Gould’s mansion Lyndhurst find it transformed into a haunted house, or a “house of curiosities.” Tickets are available here. The gothic-revival style castle is also well worth seeing in the daytime, even when it isn’t decked out in spooky regalia. The house was originally built in 1838, expanded in 1864, and purchased by the railroad baron Jay Gould in 1880. Fans of the 70s television show Dark Shadows will be thrilled to know Lyndhurst served as the principle filming location.

Matisse and Chagall’s Stain-Glass Windows at the Union Church of Pocantico Hills

Matisse Union Church
Photo: George Bremer / Flickr

Near Kykuit, you can marvel at Henri Matisse’s gorgeous stain-glass windows in the Union Church. The windows were commissioned in 1948 by Nelson A. Rockefeller, in honor of his mother, Abby. The windows were the last work of art Matisse completed before his death in 1954. When John D. Rockefeller died in 1960, his children commissioned Marc Chagall to design a window in his memory.

Food and Drink Recommendations

Fancy: Blue Hill Stone Barns

If you’re planning your trip well in advance, try to get a dinner reservation at Blue Hill Stone Barns. Dan Barber’s restaurant is one of the finest in the United States, and all the food prepared there is raised on the farm. If you aren’t in the mood for an extravagant meal, Stone Barns is usually open for a much more casual lunch (soups, salads, sandwiches) during the day, and you can take a stroll around the farm.

Great lunch: Lefteris Gyro

Do you love Greek food? Look no further than Lefteris Gyro in downtown Sleepy Hollow. The waits are long, but there are plenty of antique shops along Main Street that will keep you occupied. Once you sit down, go for the Greek Salad, but only order a large if you are starving: It’s gigantic.

Drinks: The Twisted Oak

Tourists and locals alike rave about The Twisted Oak, just down Main Street, close to the river. If you’re hungry, dinner reservations are recommended. Otherwise pop-in to the bar for small plates and cocktails.