Galloping Over the Same Old Ground: Headless Horseman Bridge

October 5, 2020 — After posting about Steve the Vampire last month (whom, by the way, I haven’t seen the two times I’ve been to Salem this season), I got to wondering if there were any other sites that we consistently try to get photos of the family at. Turns out, there really is only one other place, and no surprise, it’s still on the Halloween spectrum: The Headless Horseman Bridge of Sleepy Hollow, New York.

Now, this isn’t the actual bridge from the Washington Irving story. That one doesn’t exist anymore, and the approximate spot where it once stretched over the sliver of water that is the Pocantico River in front of the Old Dutch Church is now Broadway. So technically there’s a short, but wide bridge of concrete and asphalt on the original site, but you wouldn’t realize it just by driving over it. It just looks like an intersection.

However, that same river wends its way behind the Old Dutch Church and into the cemetery (where the Headless Horseman rises every night). There in the cemetery, a wooden bridge spans the river. The bridge is big and stout enough for cars. In fact, I can hear the sounds of cars rumbling across it as I write this, often accompanied by shouts from me or Lindsey at the kids to watch out as we all rush off the bridge to let the car pass. But the area is sylvan and secluded and the railing a rustic lattice of branches and the boards strewn with leaves in autumn. It’s a bucolic enough bridge and setting that it was inevitable that locals would call it the Headless Horseman Bridge.

For us, the tradition of getting our photos on the bridge inadvertently started in 2007, on that fateful New England road trip where so much of our lives started. And back when we carried a camera tripod around.


After that trip we didn't revisit Sleepy Hollow again until 2011. We were really focused on New England in the intervening years. In the Fall of 2008, we had just moved there, in the Fall of 2009, I was traveling for The New England Grimpendium. The Fall of 2010 was our first Fall with our first child (and the first year of the OTIS Halloween Season). But we made it back in 2011 with some friends. I was also working on The New York Grimpendium at the time.


In 2012, we returned at the invite of the cemetery for me to give a talk on the newly released The New York Grimpendium at their Washington Irving Memoria Chapel with its amazing Irving-themed stained glass windows.


We skipped 2013 for some reason, but returned in 2014, although it was in November. We were headed for Manhattan to see the Grolier Club Edgar Allan Poe exhibition, so we stopped on the way. But apparently we didn't take any photos on the bridge. The next year, in 2015, we did take some photos, but it was July 4th weekend. We knew in advance that we weren't going to be making it to Sleepy Hollow that Fall because it was the season we were going to live in Salem for A Season with the Witch.


In 2016, we went to Manhattan instead of Sleepy Hollow, but still saw Headless Horseman sites. In 2017, we mixed it up again and went to Kinderhook, New York, to see Headless Horseman sites there. 

In Fall of 2018, we couldn't go far from our local hospital because of the imminent birth of our third child, but earlier that year, during our cross-country road trip, we visited Sleepy Hollow, Illinois, and Sleepy Hollow, Wyoming, and saw the Headless Horseman in both places. 


In 2019, I made up for the absences by visiting twice. Once by myself in May to sign books as part of the Sleepy Hollow Litfest, and then that autumn the whole family returned for a couple of days, and we did Sleepy Hollow the most thoroughly that we'd ever done it and probably had the most fun we've had there.

I’m bummed that the town isn't in the Tarot cards for us this season, especially since I got so, so close when I was invited to attend a photo shoot there featuring a real headless horseman (well, the horse was real), but I just couldn't accommodate it with my work schedule. But if our past is any indication, there's always a Headless Horseman in our future.

Also 2019