Autumn Adventures in Sleepy Hollow

It’s that wonderful time of year again when temperatures start to fall, the scent of leaves fills the air, and vibrant foliage decorates the scene across New York State. If you, like me, relish a touch of spookiness along with your apple picking and pumpkin patch adventures, then a weekend trip to Sleepy Hollow, New York, is the perfect getaway.

This charming village in the lower Hudson Valley is renowned for being the real-life backdrop of Washington Irving’s eerie short story The Legend of Sleepy Hollow, which was also adapted into a film in 1999. In the story, the Headless Horseman is said to ride on Halloween night, accompanied by a host of supernatural occurrences. That’s why the village truly thrives in autumn, featuring Halloween parades, witchy decorations, and a plethora of themed activities.

Just a quick drive or a scenic train ride from Manhattan, this historic location is perfect for an extended day trip or a delightful overnight stay, with various fantastic places to eat, stay, and explore along the way. Excited to dive into the autumn spirit? Read on for our guide to experiencing Sleepy Hollow in the fall, along with other nearby attractions.

Getting to Sleepy Hollow, NY

If you’re heading to Sleepy Hollow from New York City, getting there is as easy as pie. Just catch the Metro-North Railroad Hudson Line from Grand Central Station; the express train to Tarrytown Station takes about 35 minutes. There’s also a local train to the village’s Philipse Manor station. From there, it’s a short walk or an Uber ride into the heart of town. For those driving, the trip takes about an hour and 15 minutes, although it can be longer during peak hours. If you’re traveling from farther away, the nearest airport is Westchester County Airport, roughly a 30-minute drive in White Plains, New York.

 

Chinese food dishes at Goosefeather

Courtesy All Good

Where to eat

The Hudson Valley is home to some of New York State’s most celebrated farms, so it’s no wonder that Sleepy Hollow and its neighboring villages excel in culinary offerings.

If you’re eager to fully embrace the Halloween spirit without compromising on taste, make your way to Tarrytown’s Goosefeather, where contemporary Chinese cuisine by a James Beard–nominated chef melds with a rich history. The restaurant occupies The King Mansion at the Tarrytown House Estate and is believed to be haunted by Sybil Harris, a ghost who passed away in room 293 right above the dining area. While I didn’t encounter any spooky sights during my recent visit, numerous guests and staff have reported strange occurrences throughout the years.