Sleepy Hollow, 2017

Sleepy Hollow, 2017

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Before I ever moved to New York, I knew I wanted to visit Sleepy Hollow during October. I even put it on my silly list of things to do before I turn 30, and I crushed that goal. I'm now 32 and Sunday was my fourth (mostly) annual trip upstate to the village formerly known as North Tarrytown. 

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I'm embarrassed to say that it took me far too long to read The Legend of Sleepy Hollow short story by Washington Irving. I don't know why I waited so long to pick it up—and the story is less than a hundred pages, so it only took me a day to read—but it definitely added to my enjoyment and appreciation of the area.

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It might seem silly or pointless to revisit the same tiny town year, after year, but I'm always seeing something new. There is also a comfort to holiday rituals, and as soon as the leaves start to turn and I feel a chill in the air (something woefully missing this year—it was nearly 80 degrees on Sunday), I start looking forward to the fall pilgrimage. This year's group of adventurers included some newcomers, and it's nice to be able to introduce people to Sleepy Hollow and share the places that I've come to love so much. 

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This year we spent the bulk of our time visiting two historic houses in the area—Washington Irving's Sunnyside and the Rockefeller estate, Kykuit—so we didn't have a lot of time to wander. We briefly peeked into the cemetery but unfortunately it had already closed for the day, and we ended the night screaming (and laughing) our way through the outdoor haunted maze, Horseman's Hollow

I love that the village of Sleepy Hollow has come to embrace their famous legend—the headless horseman is everywhere, showing up on their street signs, police uniforms, fire trucks and school mascots—and I would imagine that locals either absolutely love Halloween, or grow to hate the influx of visitors. Every year I find myself discovering a lovely house with a mansard roof, cornstalks tied to columns or pumpkins on a porch and thinking that it must be the most wonderful place in the world to call home—but living just an hour train ride away isn't too bad either. 




Places to eat: Horsefeathers

Charter Street Cemetery

Charter Street Cemetery

Muffler Man: Bunyan + Babe

Muffler Man: Bunyan + Babe