Losing Our Heads in Sleepy Hollow

October 23, 2011 — I just left my heart in Sleepy Hollow. Better than leaving my head, I guess.

A few years ago, I wrote a 3,500-word piece on Sleepy Hollow, NY, and its neighbor village of Tarrytown for O.T.I.S. In it, I explained that the town was the place where Washington Irving lived and was buried. That it was here he set his famous story The Legend of Sleepy Hollow using the actual landmarks of the area. And that the town has fully embraced its patron author, headless spook, and important place in American literary history.

However, upon my recent visit this past weekend, I realized that I just didn’t do the village justice. The two-part piece explained why the place has images of decapitated horse jockeys everywhere you look and pointed out the best Washington Irving and Legend sites, but it didn’t quite capture how magnificent the area looks in Autumn, or how much every house and business downtown embraces Halloween as a whole, or just how splendid the historic estates in the area are.

And I’m going to accept that I’m just not up to the task to get out of the task this time. However, below are a few pictures we took on this trip. More pictures of the actual famous landmarks of the town can be found in the above-criticized article.

If you’ve never been to Sleepy Hollow in Autumn, you really need to head there. Just don’t expect to bring yours back.

Philipsburg Manor

Tarrytown's Lyndhurst mansion has been hosting a
scarecrow event on its premises throughout October.

Said Lyndhurst mansion.


Okay I just want to tell you how much I really love your Halloween blogs. I know it doesn't get the recognition that O.T.I.S does, but I'm sure there are many resolute readers out there who love Halloween just as much as you do. Lord knows, I'm one of them.

I love living in Atlanta (I'm a Southerner born and bred) but I must say that our Autumns just do not hold a candle to what you get in New England. That's why I'm glad I get to enjoy it vicariously through your blog. I have vowed that someday I WILL experience a New England Halloween for myself. So, my question is, does Sleepy Hollow get as crazy as Salem does during the Halloween season? If I'm flying all the way up there to experience the glory that is Halloween in New England, I'd rather not have it ruined by having to deal with tons and tons of people everywhere.

Hey Chris,

Thanks so much for the kind words. I love doing the Halloween Blog both because of how great Halloween is but also because it frees me up to write about a wider variety of topics, as opposed to OTIS, where it's much more a travel-centered blog. It makes me happy that other people dig it.

Sleepy Hollow can get crowded at peak times, but not in the "dangerous party" way that Salem does. Just to give some perspective, Salem's a city and twice as big population-wise as the villages of Sleepy Hollow and Tarrytown put together.

Full disclosure, though, I've been to Sleepy Hollow much fewer times, and kind of romanticize it more as a result. With that in mind...

A big difference atmosphere-wise is that parts of Salem can feel really, well, carnivalesque, might be the most balanced term. Sleepy Hollow isn't quite as capitalized on.

Halloween fans need to do both, though, if they can at some point in their lives, and the comparison might just come down to whether you like witches of the headless horseman better.

Anyway, it's a good question and wish I'd of though of it earlier in the season so that I could do a post to really break down the comparison. Maybe next Halloween.

Thank you for taking the time to respond. I would love to see you do a comparison next Halloween. Hmmm..carnival atmosphere in Salem, eh? Well I was born in New Orleans so I'm familiar with that, maybe a little too familiar (hence my aversion to crowds now). I will try to get up to New England some fall and putter around Sleepy Hollow. I think I'm just a "Horseman" kinda gal.

Thanks again!

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