I’ve long been a fan of J.W. Ocker. Many of his spooky sensibilities have always seemed to align with my own (his opinions on writing scary books for kids in particular, but also his deeply personal, almost ritualistic approach to Halloween). Mostly, though, his writing is always a treat. I read A Season with the Witch, that passionate portrait of Salem, Massachusetts, a couple of years ago, and had such a blast with it that I’ve revisited it a couple of times since. So when I learned that he was giving the same treatment to the village of Sleepy Hollow, the setting of one of my favorite stories and one of the places I most wish to visit—well, I couldn’t not be excited. Chasing the Headless Horseman: The History, Hijinks, and Halloweens of the Real Sleepy Hollow is, as I’d hoped, every bit as exhaustive and enthusiastic as its witchy predecessor, and I had a great time with it.
It is, admittedly, a bit drier than that previous book. A considerable portion of Chasing deals with what Ocker perceives as something of an identity crisis in Sleepy Hollow—both literally, with the village’s relatively recent name change (1996 is still recent do not @ me), and existentially, as a place that would like to capitalize on its reputation as a Halloween destination without letting its substantial historical significance be overshadowed by the holiday’s more kitschy, touristy trappings. It’s a tension Ocker explores throughout the book with his usual inquisitiveness and diligence, but one that he perhaps spends a little too much time trying to untangle, making for a somewhat less lively reading experience. Season, on the other hand, is all about a peculiar place that has fully embraced its peculiarity, which, to me, makes for a more entertaining read.
It makes for a fascinating contrast between the two books: one is about a city that has managed to balance a very real and very tragic history with the more frivolous aspect of its Halloween celebrations, while the other is about a small town with a literal work of literature as part of its foundations that is still struggling to find a more cohesive identity. Which maybe says something about the way America seems to capitalize on sensational violence much more readily than on its artistic endeavors. But that is, I’m afraid, an entirely different topic for another time.
Chasing is not without its share of fun, though. Ocker’s interactions with the locals are always as illuminating as they are amusing. The chapter exploring other, considerably less headless legends of Sleepy Hollow country is a standout, but the one in which Ocker subjects himself to endless hours of Headless Horseman media might be one of my favorite things he’s ever written (some of the adaptations sound so spectacularly absurd that I’ve already looked them up and hope to watch them before the season is over).
And for Ocker, it all goes back to that galloping goblin (the man has a Headless Horseman-themed bathroom, after all). His book on the Witch City may be more immediately fun and engaging, but the deep, abiding affection he has for “The Legend,” its celebrated author, and the quaint, quiet bit of land that inspired him is palpable, making this, in my opinion, the more earnest and heartfelt volume. 