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Philipsburg Manor, Sleepy Hollow | © Wikipedia Commons
Philipsburg Manor, Sleepy Hollow | © Wikipedia Commons
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A Guide To New York's Sleepy Hollow

Picture of Dana deLaski
Updated: 30 September 2016
Sleepy Hollow is a village in Mount Pleasant, New York, but it’s become known as a Halloween town thanks to Washington Irving’s short story ‘The Legend of Sleepy Hollow’. The story, about the town ghost – the Headless Horseman – has gained such popularity (now there’s even a TV show called Sleepy Hollow) that the town is often deemed the most haunted town in America. Washington Irving himself is buried within Sleepy Hollow, and the most popular things to do in the town are associated with the famed short story.

Getting to Sleepy Hollow from Manhattan is easy: the train from Grand Central Station only takes about 30 minutes, and the best option is to get off at Philipse Manor instead of Tarrytown.

First and foremost, if you’re a fan of ‘The Legend of Sleepy Hollow’, you can visit Washington Irving’s house in Tarrytown (if you want to do this, consider getting off the train at Tarrytown). The house is called Sunnyside, but don’t be fooled: you may encounter ghosts. Next, be sure to visit Old Dutch Church and Old Dutch Burying Ground, the place where Washington Irving’s story began. This is where the Headless Horseman chased Ichabod Crane in the story, and now there are free guided tours of the area. If one cemetery isn’t enough for you, next check out Sleepy Hollow Cemetery, where Washington Irving himself is buried, alongside other notable figures like William Rockefeller, Walter Chrysler, and Andrew Carnegie.

Old Dutch Church at Sleepy Hollow
Old Dutch Church at Sleepy Hollow | © Daniel Case, Wikipedia Commons

Next, head to the Horseman’s Hollow at Philipsburg Manor Upper Mills, the site where Ichabod Crane saunters with ‘country damsels’ in the story. For special events, the building is transformed into the ‘Horseman’s Hollow‘ – a haunted house that’s sure to make you squirm. You can spend an entire day following in the footsteps of Ichabod Crane, but expect some spooky sites and potential ghost encounters.

Although it’s a major draw, if ‘The Legend of Sleepy Hollow’ isn’t interesting to you, you can always check out the Union Church of Pocantico Hills, which features stained glass windows by Henri Matisse and Marc Chagall. The rose window here was Matisse’s last work before his death.

Last piece of work by Matisse

A photo posted by Kayla Gerhardt (@10kg) on

Sleepy Hollow is also an outdoor lover’s paradise. If you’re into hiking, horseback riding, fishing, or birdwatching, head to Rockefeller State Park Preserve to do it all. Alternatively, you could go for a hike or a bike ride in the Old Croton Aqueduct. You can also take a guided kayak tour down the Hudson River if water sports are more your thing.

For dinner, there are lots of reasonably priced options in town, but if you want one of the most memorable dining experiences of your life, check out Blue Hill at Stone Barns, a world-famous restaurant that happens to be in the neighborhood. Blue Hill was a pioneer of the farm-to-table movement; the restaurant is situated on its own farm, where all the ingredients for their lengthy, multi-course tasting menu are grown. Chef Dan Barber is known to be one of the best chefs in the United States, and a trip to his restaurant and farm would be a meal of a lifetime.

Whether you’re in Sleepy Hollow for a spooky experience or simply as an escape from the city, it’s a picturesque getaway full of things to do. Despite being known as one of the most haunted towns in America, you could easily come here and simply enjoy its slow pace of life and stunning landscape. Just don’t be surprised if you encounter a friendly ghost or two along the way.

Morning serenade.

A video posted by BlueHillFarm (@bluehillfarm) on