October 5, 2019: Sleepy Hollow, Day 1 of 2

Within minutes of our arrival in Sleepy Hollow, New York, we found ourselves in the place we would be every morning if we lived in the area: Sleepy Hollow Cemetery.

It’s one of my favorite cemeteries, a large park full of a variety of funerary art, interesting interments, and landscape features. But mostly I like it because it’s the home of the Headless Horseman in Washington Irving’s story. I could spend hours walking through it, imaging him racing along its paths.

The famous rotyard is a little bit different in October. More [living] people are there, at least as far in as Washington Irving’s grave. It’s also fluttery with signs, signs, everywhere a sign—signs repeating the closing time of 4:30, signs telling people not to park on graves, signs blocking off roads to vehicular traffic, signs pointing out where tours start. You can tell the cemetery staff has been through far worse than a decapitating soldier ghost.

We started, as we always do, at the Headless Horseman Bridge. No the real one, which is no more (although its placement is somewhere in front of the Old Dutch Church at the front of the cemetery), but a little ways inside the cemetery, there’s a rustic bridge over a stream that seems like the kind of place a wiry schoolteacher could face off with a hellish horse rider. We’ve been taking family photos there since this family of five was a family of two.

From there we wandered the stones and the hills and the mausoleums. We checked in on Washington Irving and found a miniature harvest party, with lots of people taking photos of his grave and a plot decorated with pumpkins and straw and mums, a tiny jack-o-lantern. We saw the crypt from Dark Shadows just beyond Irving, found the newly laid gravestone of the previously unmarked plot of Hulda, the Witch of Sleepy Hollow. I met my friend Jim, who runs the place, tooling around in his black pickup with the cemetery name and a Headless Horseman symbol on the side door.

I showed my family Sleepy Hollow’s other specter, the Bronze Lady, a cursed statue and mausoleum that I only learned about earlier this year from Jim and which will show up in my Cursed Objects book next year. This one was a lot of fun, because it was apparently the first time my five-year-old had ever heard the concept of a curse. And, boy, did she want to bring it down on her. My oldest wouldn’t go near the statue, even when I tried to drag her over there. My five-year-old did everything she could to get cursed on purpose, including assaulting the statue and peeking into the keyhole of the mausoleum.

The rest of the day, she kept asking, “Where’s my next curse?”, meaning “When does bad stuff start happening?” Later, we were eating at Horsefeathers (which decorates extremely well for the season and has a year-round mural that includes both Washington Irving and Edgar Allan Poe), when the light in our booth started flickering. “Curse,” she said, nodding her head sagely. Her first words the next morning when she awoke in the hotel room was, “I didn’t have a nightmare,” which is supposed to be one of the side-effects of the curse. She sounded disappointed.

After that, we wandered the town, saw the Headless Horseman statue, the pumpkin monster that’s always seasonally tied to that clock at the intersection of Broadway and Beekman. I showed the girls the start of the Headless Horseman’s chase route at the Major Andre’ Captors monument, and then relaxed in our hotel room until it was time for the Great Jack-O-Lantern Blaze at Van Cortlandt Manor in Croton-on-Hudson.

This is one of those events where they carve thousands of real and fake pumpkins, assemble them together into larger objects and scenes, and fill the landscape with lighting and fog effects. It’s the Halloween equivalent of a Christmas light show, and it’s awesome. I wrote about it back in 2012 after my second visit (my first was in 2007).

We had tickets for the 6:30 walk-through, but it wasn’t quite dark enough. So we hung back and drank cider and orange-frosted baked goods until dusk had fallen enough, and then we were treated to jack-o-lantern windmills and skeleton horse carousels and fields of zombie and dinosaur pumpkins. It was glorious.

Then we went to bed at our hotel just outside of town, knowing we would get to do even more Sleepy Hollow on the next day.

I've put together separate photo essays on our visits to Sleepy Hollow Cemetery and the Great Jack-O-Lantern Blaze. You can also listen to my thoughts on how to do Sleepy Hollow on Odd Things I’ve Seen: The Podcast, which I recorded before I left for the Hudson Valley. Listening back to it now, I undersold how crowded the place could be, but also undersold how cool the place is.