Sleepy Hollow and Tarrytown at Halloween

My friend Mary texted our group chat one day and said “let’s go to New York!” I said “Is a bean green?” And we planned it. Actually, she’s the most Type A among us, so *she* planned it. It was not what I would have planned . . . and I am glad. I’ve been to Manhattan many times, and while there is always something new and exciting to experience in a city that is forever changing, those visits start to run together in my memories. And I love new adventures! Even though I was an English major and took classes in early American literature, I had not given much thought to whether Sleepy Hollow and Tarrytown were real places as opposed to fiction in the mind of Washington Irving. They are real.

But first . . . along with our friend Elizabeth, we visited Manhattan – of course. We felt the rush of the City. We went to a taping of an amazing show, we had a delicious dinner with one of my best friends from childhood and his wonderful wife, I shopped at the Chelsea Flea while Elizabeth saw a matinee and Mary went to lunch with a friend, we walked around Times Square, and we absorbed the NYC energy. And on the morning of our Sleepy Hollow Adventure, we walked to Grand Central Station and caught the Metro-North Railroad Hudson Line train to the Irvington Station. It’s a beautiful ride that takes less than an hour. And very close to the train stop is an organic coffee shop called the Red Barn Bakery with organic pumpkin ice cream and blueberry scones. We got our provisions and ordered our Uber to take us to Sunnyside, Washington Irving’s homeplace in Tarrytown – where we had tickets to tour the grounds and home.

I am writing this like an expert, but truly none of this is anything I knew before Mary planned this trip. It was Halloween weekend and apparently tickets to Sunnyside become scarce this time of year because lots of people want to see the home of the man who imagined the headless horseman. If you want tickets to Sunnyside, be like Mary and book them here ahead of time through Historic Hudson Valley. They give you a time slot to show up, so it was super important that we were on time – and we were. Because Mary. Apparently this ticketing thing was news to a few people who showed up around the same time we did – and were not pleased with the fact that they could not get in. In that moment I was very glad Mary is such a planner.

Washington Irving was born in 1783. He was a lot of things, including a lawyer and a diplomat, but mainly he is known for writing the short stories “Rip Van Winkle” (1819) and “The Legend of Sleepy Hollow” (1820). If you don’t remember, Rip Van Winkle is the very relatable story of the guy who went to sleep and didn’t wake up for a really long time and everything changed while he slept.

“All these, however, were mere terrors of the night, phantoms of the mind that walk in darkness; and though he had seen many spectres in his time, and been more than once beset by Satan in divers shapes, in his lonely pre-ambulations, yet daylight put an end to all these evils; and he would have passed a pleasent life of it, in despite of the devil and all his works, if his path had not been crossed by a being that causes more perplexity to mortal man than ghosts, goblins, and the whole race of witches put together, and that was – a woman.”
― Washington Irving, The Legend of Sleepy Hollow

His house was especially cute and the tour guides enthusiastically knew all about Washington Irving and his life. They had many activities for children there too. It would be a wonderful side trip for young parents with children who would like a bit of peace and tranquility in an otherwise hectic New York City vacation.

But Tarrytown is a small hamlet compared to Sleepy Hollow. That was our next stop. Here’s how Irving described Tarrytown from the point of view of a Sleepy Hollowian:

“Not far from this village, perhaps about two miles, there is a little valley or rather lap of land among high hills, which is one of the quietest places in the whole world. A small brook glides through it, with just murmur enough to lull one to repose; and the occasional whistle of a quail or tapping of a woodpecker is almost the only sound that ever breaks in upon the uniform tranquillity.”
― Washington Irving, The Legend of Sleepy Hollow

This is the comparatively bustling Sleepy Hollow:

So . . . we were soon on to the big city where they were gearing up for their annual Halloween Parade.

The Halloween Parade in Sleepy Hollow, as one might imagine, is a very big deal. But my friends and I are not big fans of crowds, so we walked on to the Dutch Church and cemetery, where we were able to see Washington Irving’s final resting place.

I highly recommend this excursion from Manhattan – especially this time of year. I also recommend reading or listening to The Legend of Sleepy Hollow. It challenges the mind in a way I don’t think we’re challenged often enough these days.

This is also an appreciation post for friends like Mary who plan things so the rest of us can enjoy them as if they’re just unfolding like magic.