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A Sleepy Hollow road trip filled with Headless Horsemen

It's Halloween year round in the New York village made famous by Washington Irving's short story

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Created by Roadtrippers - October 13th 2020

Located just about an hour north of New York City in the Hudson River Valley is the village of Sleepy Hollow. Although Washington Irving published his classic short story The Legend of Sleepy Hollow in 1820, the village was known as North Tarrytown and didn't officially adopt the nickname until 1996. The village is small, but it definitely embraces its association with Halloween, and has fully adopted Irving's Headless Horseman as its mascot. He appears on everything from street signs to fire trucks, sanitation vehicles, and police badges—even the high school football team is called The Horsemen.

The area is beautiful year round, but it really comes alive—much like the Horseman himself—in the fall. As Irving wrote, “If ever I should wish for a retreat whither I might steal from the world and its distractions, and dream quietly away the remnant of a troubled life, I know of none more promising than this little valley.”

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Washington Irving's Sunnyside

There is no doubt that The Legend of Sleepy Hollow is the reason why the area is a popular fall destination. Purchased by Irving in 1835, Sunnyside is a National Historic Landmark and a museum containing a large collection of Irving's original furnishings and personal items. Located in the nearby town of Irvington, the house is open between May and November and tours are led by guides in period costume.

Tarrytown, NY

Lyndhurst, a Gothic Revival mansion, was designed in 1838 and had five different owners from three different prominent families before it became part of the National Historic Trust for Preservation in 1961. The mansion is furnished with original furniture and décor from all five owners, making the inside just as historically interesting as the outside. The 67-acre grounds include the bones of the nation's first steel-framed conservatory, a stand-alone bowling alley, a rose garden, and a children's playhouse, all with sweeping views of the Hudson River.

Open for tours between March and December, the mansion and grounds are decked out for Halloween in the fall. Even without the extra help, Lyndhurst is spooky enough all year—it's been featured in numerous movies and TV shows including two star turns as the Collinwood Mansion in the '70s films House of Dark Shadows and Night of Dark Shadows.


Family owned since 1981, Horsefeathers is exactly the kind of dark, wood-paneled bar that you’d expect to find in the area. Settle in to a booth and order the Knickerbocker burger and a seasonal cider. If you're lucky, a Halloween-themed movie might be playing at the bar, and every table comes with its own box of vintage Trivial Pursuit cards.


Sleepy Hollow, NY

Kykuit is a 40-room house that was built for John D. Rockefeller, founder of Standard Oil and noted philanthropist. The stone mansion is situated on the highest point in Pocantico Hills, overlooking the Hudson River. On a clear day you can see the New York City skyline. In addition to the house, the property includes beautiful gardens and an impressive art collection. Although Kykuit is located outside of Sleepy Hollow, tours originate from the visitor center at Philipsburg Manor (across from the cemetery) and a shuttle bus takes you between the estate and the village.

Union Church Of Pocantico Hills

The Union Church of Pocantico Hills, built in 1921 by John D. Rockefeller, Jr., may look unassuming, but its Rose Window was the last work completed by Henri Matisse before his death in 1954. Nine other stained glass windows were created by Marc Chagall. The church is open between April and December with varying hours depending on the worship schedule. There is a suggested donation if you visit just to see the windows, and photography is not allowed inside. The church is up in the hills, just a short drive from Sleepy Hollow.


Sleepy Hollow, NY

Sleepy Hollow Cemetery is home to a number of famous residents, including a Rockefeller, a Chrysler, the Helmsleys, Andrew Carnegie, Elizabeth Arden, and Washington Irving himself. Formally opened in 1849, the cemetery is 85 acres and has more than 40,000 in-ground interments. Day and night walking tours are offered, but if you’d like to explore on your own, keep in mind that the grounds close promptly at 4:30 p.m. every day.

Headless Horseman Bridge

While at the cemetery, you can see the Headless Horseman Bridge—or, at the very least, an old bridge similar to the one where Ichabod Crane had his famous encounter with the Headless Horseman.

Croton-on-Hudson, NY

Van Cortlandt Manor is a great place to stop by and experience the rich Dutch history that played a role in Irving's story. In the fall, the grounds come alive with more than 7,000 hand-carved pumpkins at the Great Jack O'Lantern Blaze.

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Banner Photo Credit: Alexandra Charitan


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