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Debbie Downer Goes To Sleepy Hollow//October 128th, 2022

 Most people who know me, know that Sleepy Hollow, New York is what I call my heart’s home.

It was a place that had been on my “bucket list” to visit practically since the cradle, and I first took a drive through the town on Halloween 2018, on my way to my first ever experience at The Great Jack O’Lantern Blaze. Though I wasn’t there for very long at all, as it was just a quick detour, I immediately felt at home, as if this was some place I’d been waiting to find for my entire life. I thought about it constantly until I went back to stay for a few days for Halloween 2019, and I knew during that stay that this was my place. It’s a hard thing to explain, but it’s like one of those moments that you think only occurs in fiction, when the stars align and you just know you’re exactly where you’re supposed to be. 

I initially planned to take different spooky-themed vacations every Halloween, maybe going to Salem one year, Spirit of Halloweentown in Oregon the next, etc., and while I do still hope to see those places, and more, one day, I realized very quickly during my 2019 stint in Sleepy Hollow that this was the only place I wanted to be on the most important day of my year. It’s just where I belong.

Thankfully I am close enough to Sleepy Hollow that I find ways to visit throughout the year, mainly spending time in the cemetery among the dead who I’ve come to think of as friends, providing me with constant curiosities and much research once I leave them. But it hurts my heart not be there more permanently. I lament this often in different things that I post, to the point where I’m sure even some of my closest friends and most loyal followers are probably sick of hearing about it. I take so many pictures during each of my visits that I post frequently about the town no matter how long it’s been since I’ve physically been there. My love for the town is far, far from a secret.

And yet, nearly every time I post about it, I get either comments, direct messages, or both, telling me how disappointed or underwhelmed they were when they visited Sleepy Hollow. Some of them are just curious fellow Halloween lovers, who clearly didn’t feel the same way I did upon my first visit and genuinely want to make sure they didn’t miss anything important, but the vast majority of these people, some of whom are actually followers of mine and have been for awhile, seem to just delight in telling me how much they think my favorite place sucks. 

I understand that everyone likes different things. I take absolutely no issue with someone not being as enchanted with Sleepy Hollow as I am. However, I’d be lying if I said I didn’t think it was kind of crappy to try and strike up a conversation with someone, about something that clearly means a lot to them, just to complain about it. I mean, what do you really get out of it? I’m not going to suddenly agree with you, and say, “You know what? You’re right! This place that has come to mean more to me than anywhere I’ve ever actually lived, is actually the most boring place in existence, and I’m so embarrassed that I’ve wasted so much time there in recent years!” (Damn, that was excruciating to write.) Pro tip: If you’re looking for someone to vent with you about something, you might want to reach out to someone who doesn’t clearly have the exact opposite opinion.

With that said, I suppose I can understand why some people might be a little underwhelmed by Sleepy Hollow. My only complaint about it is that it’s not a Halloween-shopping hotspot like I’d initially hoped,  but the magic around the place makes up for that in spades. Also, for new visitors of the past two years, the lack of events going on due to Covid may have been a little disappointing, but again I’m left to wonder why these visitors can’t see the magic without a huge spectacle going on.

I think the thing about Sleepy Hollow is, in comparison to what I’ve seen of places like Salem or Spirit of Halloweentown or even just your average haunted house, its magic is much more subtle. Sleepy Hollow isn’t an “in-your-face” type of experience. It’s a feeling, not a constant party. There are echoes all around of the Legend and other spooky things, you just have to be open to noticing them. And, though many of these people from my DMs would surely argue, I can assure you that the spirit of Halloween is there, all around, no matter what the calendar says. 

Perhaps it’s because I’ve always been able to find Halloween when everyone tried to tell me it wasn’t there. For almost as long as I can remember, I’ve spotted signs of Halloween in the strangest of places. The ghosts that seem to form when the wind blows on a snowy afternoon. The way my mind immediately pictures what the leaves will look like in the fall, when they’ve only just returned in the spring. The smell of summer bonfires, where each crackling flame seems to whisper It’s coming… Halloween has never been just a once-a-year thing for me. I know how to find it, even if I’m not fully aware that I’m looking for it in a particular moment, and Sleepy Hollow just ignites that flame like nowhere else, whether it’s the hottest summer day or a chilly winter afternoon. 

Maybe that’s the difference between those of us who are in a Halloween mindset all year round, and those who enjoy the holiday on a more seasonal level. When Halloween is truly your heart and soul, you don’t need it to be presented to you in such an “in-your-face” type of way to know that it’s there. There’s a thread of magic that is always present, picking up on all of the little signs that it can find. I suppose I can understand why Sleepy Hollow might be disappointing if you have an absolute need for an in-yout-face party atmosphere, but more than anything, I suppose I should be most grateful that I don’t fall into the category of people who can’t see or understand its magic. 

Not everything is for everyone, and I completely understand and respect that. But I have no real understanding or respect for people who have to be negative about something, directly to someone that they know loves it. If you visit a place, and it’s not what you were hoping for, it’s easy to simply just move on and find your own magic. 

Stay spooky, my friends. And be kind to one another. May we all someday find a place in the world that speaks to us.

(For the record, I always feel him standing there, even when he isn’t. And PS, yes, I dress like this all the time.)


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