The Best Things to Do in Sleepy Hollow New York Beyond Halloween


It’s that time of year when we’re all looking for a little scare and colorful foliage mixed in with our fun, and one of our favorite weekends from Manhattan has it all. Shovel: Sleepy Hollow, New York. While this village in the lower Hudson Valley is famous for being the actual setting of Washington Irving’s short story The Legend of Sleepy Hollow, which was also a 1999 movie, there’s a lot more to explore here than just historical landmarks (although there are plenty of those too). And there’s plenty to see beyond the popular autumn season, whether you want modern international cuisine or exhilarating outdoor activities like hiking and biking. Here’s our guide to this quaint upstate New York town, as well as what else there is to discover nearby.

Getting to Sleepy Hollow NY

Traveling to Sleepy Hollow can be accomplished via a few options. From New York, travel time is approximately one hour and 15 minutes (but can be much longer during rush hour). You can also hop on the Metro-North Railroad Hudson Line from Grand Central Station; the express train to nearby Tarrytown station takes only around 35 minutes, and there is also a local train to Philipse Manor station in the village. If you’re coming from further afield, the nearest airport is Westchester County Airport, located about a 30-minute drive away in White Plains, New York.

Kykuit Estate is the former home of philanthropist John D. Rockefeller.

Jaime Martorano / Historic Hudson Valley

What to do: Historic homes and leisurely hikes

New York’s Hudson Valley is filled with elegant historic homes, charming main streets, and scenic hiking, biking, and walking trails. But even for the area, Sleepy Hollow and its neighboring towns of Tarrytown and Irvington have an inordinate number.

In Sleepy Hollow proper, the historical sites are the biggest draw. Fans of the spooky will definitely want to visit Sleepy Hollow Cemetery, which is the final resting place of a wide range of famous personalities, including Washington Irving, Andrew Carnegie and Elizabeth Arden. Remember, this is still a working cemetery, so it’s important to be respectful. Philipsburg Mansion is a fascinating step back in time: in the 1750s, the estate was run by a community of two dozen slaves of African descent and featured a bustling trading complex and mill, which you can experience on a tour. Unsurprisingly, the most visited place in the city is the Headless Horseman Statue, created by local artist Linda Perlmutter. And finally, one of the most famous mansions in the state is located here: Kykuit, the former home of philanthropist John D. Rockefeller, the founder of Standard Oil, and is a short drive from Rockefeller State Park Preserve. The Classic Tour of the estate, which lasts over two hours, gives you an excellent overview of this impressive presbytery.

In close proximity to Irvington, however, is actually Washington Irving Estate, sunny side. The charming, rambling house sits on the banks of the Hudson River and offers tours on weekends from May through September. And one of Westchester’s most architecturally unique homes is also in town: The Armour-Stiner Octagonal House, As you can probably guess, it is an eight-sided house that is the only fully vaulted octagonal residence in the world. Guided tours are offered from April to December (we recommend the Halloween tour to learn all about the mysteries of the house). From there you can head to Irvington Woodsa tranquil reserve with over 40 miles of hiking, biking and running trails.

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