Ichabod Crane Would Have No Chance in Today’s Sleepy Hollow

October 27, 2023 —
Headless horsemen galloped everywhere. An entire heard of them. On murals and advertisements. On Halloween décor and in gift shops. On street signs and business names. Kicking up colorful leaves under the hooves of their steeds and brandishing flaming jack-o-lanterns in their hands.

Ichabod Crane would have had no chance in today’s Sleepy Hollow. Especially at this time of year.

We drove through town, following the chase route along Broadway, from the Major Andre statue to the bridge and past the Old Dutch Church into one of my favorite cemeteries in the country. It was crowded, as it always is at this time of year, so many cars it was almost more parking lots than grave plots. But the trees were aflame with the fires of fall, a bower of red, yellow, and orange beauty over the similarly multi-colored dead below. We drove past all the old haunts—Washington Irving’s grave and the Headless Horseman Bridge and the historic plaque—but didn’t stop and get out until we found ourselves in a less traveled and less trammeled part of the cemetery, where we met up with the Bronze Lady, Sleepy Hollow’s resident cursed object. We were nice to her, although my middle child lingered longer as we walked away, trying to be extra nice to her.

We left the cemetery, pausing for a moment to wonder whether we should take our one millionth photo with the gorgeous sculpture of the chase scene that looms outside the cemetery gates, but then continued to downtown Tarrytown, where we parked and tarried. We took photos of all the scarecrows tied to the lampposts, gazed at all the spooky art painted on the glass windows of the shops, stopped for ice cream, and considered buying our one millionth Headless Horseman souvenir. But overall, we just took in the feel of a town vibrating on the edge of their annual Halloween parade.

From there, it was on to Lyndhurst Mansion, a castle so gothically perfect it was chosen as the home of the ghouls and haunts and romances of the two Dark Shadows movies. There, a room full of people ignored the bounty of Halloween adventure that Sleepy Hollow has to offer to listen to me make a case for which city is the better Halloween Town, Sleepy Hollow or Salem. One day I’ll share my stringently quantitative findings with a larger audience.

After Lyndhurst, it should have been dinner at Horsefeathers and then a winddown at our hotel, but we decided to see an old friend instead. We crossed the Tappan Zee Bridge out of Sleepy Hollow. As we did so, my middle child surreptitiously lowered her window. I shot her a questioning look, and she said, “We just visited a cursed object, Dad. If this bridge goes down and we fall into the water we need to be able to swim out of the car.” Her wisdom was a mixture of YouTube how-to’s and that Final Destination marathon we did a couple of weeks back.


An hour drive took us to Middletown, New York, to the Paramount Theater, where a three-day horrorthon was in progress. Out in the lobby of that august movie temple, a table full of props from classic horror and science fiction movies was lovingly attended by their caretaker Joey Vento of Haunted Barn fame. I met Joey when I wrote about his collection for The New York Grimpendium fourteen years ago. After a magic visit where the past of old movies collided with the present of my young daughters and old friends deepened their friendship, we drove back to the hotel.

Last year, we did almost the exact same Sleepy Hollow jaunt, but with a fifth member of our party, their heart ugly and poisoned with bad secrets and treacheries, their blank face and smile a concrete Halloween mask against reality and beauty.


Which is why I’m ecstatic that today was not just a great autumn day, a great Halloween day, but a great day full stop. The shadows of the past were chased away by the larger shadow of the Horseman, if only temporarily. At the very least, I don’t know how a broken, middle-aged dude and three beautifully chaotic daughters could have done it better. I don’t know how many could have done better.

The girls are all passed out in the hotel room as I write this. They didn’t even make it through Hocus Pocus on Freeform. I’m barely making it through Bride of Frankenstein on TCM. The exhaustion is settled into my own skeleton as I post this. Boris Karloff just told his bride, “We belong dead,” and blew up the castle.

And, as loathe as I am to end this day, I belong dead…asleep.