It’s the best time of year again, when temperatures begin to drop, the smell of leaves hits the air, and colorful foliage can be found all around New York State. If you, like me, enjoy a bit of fright with your apple picking and pumpkin patch visits, there’s no better weekend getaway than one to Sleepy Hollow, New York.
This village in the lower Hudson Valley is famous for being the real-life setting of Washington Irving’s haunting short story The Legend of Sleepy Hollow, which was also made into a 1999 movie. In the tale, the Headless Horseman is said to appear on Halloween night, and plenty of paranormal phenomena occur. That’s why the village truly comes alive during fall, when you can find Halloween parades, witchy decor, and plenty of on-theme activities.
Just a quick drive (or stunning train ride) from Manhattan, this historic site is ideal for an extra-long day trip or a fun overnighter, with plenty of great places to eat, stay, and play along the way. Ready to get in the spirit? Read on for our guide to Sleepy Hollow in the fall, plus what else there is to discover nearby.
Getting to Sleepy Hollow, NY
If you’re traveling to Sleepy Hollow from New York City, it’s almost too easy to get there. Simply hop on the Metro-North Railroad Hudson Line from Grand Central Station; the express train to nearby Tarrytown Station only takes about 35 minutes. There’s also a local train to the village’s Philipse Manor station. From there, you can walk or take a short Uber ride into the main part of town. For those traveling via car, the drive time is about an hour and 15 minutes (though it can be much more during rush hour). If you’re coming from farther afield, the closest airport is Westchester County Airport, located about a 30-minute drive away, in White Plains, New York.
Where to eat
The Hudson Valley boasts some of New York State’s most famed farms, so it’s no surprise that Sleepy Hollow and its surrounding villages punch well above their weight when it comes to restaurants.
If you’re looking to embrace Halloween to the fullest extent (while not sacrificing on flavor), head to Tarrytown’s Goosefeather, where modern Chinese food served up by a James Beard–nominated chef meets a haunted past. The restaurant is located in The King Mansion at the Tarrytown House Estate, and is said to be the home of Sybil Harris, a ghost who passed away in room 293 just above the dining area. While on a recent trip there, I personally wasn’t visited by any ghostly apparitions, but previous guests and staff have reported plenty of mysterious happenings over the years.
