Lil’ W. and The Legend of Sleepy Hollow

Lil W

Back in the day when I was a diminutive child with a pageboy haircut, oversized glasses, and a superstitious nature, I had a strange fascination with The Legend of Sleepy Hollow. I can’t recall how I heard the story. It must have been told to me at some point (I was still in the picture book stage of my reading comprehension). I just remember being absolutely fascinated by the story and accepting it as fact. I still readily believed everything that was told to me, whether or not it seemed like obvious fiction.

My entire life I have been both terrified and fascinated by dark and macabre subjects, and that story was just what I needed to become completely obsessed. My parents bought me the animated Disney movie version which I watched again and again with delight and terror. They also took me to a theater production of the story. I closed my eyes during the Headless Horseman scene, yet was still full of glee over the experience.

I think my mom in particular found my gullibility adorable, because she decided to feed into my magical beliefs. I truly took The Legend of Sleepy Hollow to be fact, and my favorite part of American history. So, it seemed very natural when, during a short road trip in Wisconsin, my mom parked the car next to a covered bridge in a wooded area, turned around to me and my sisters in the backseat, and announced, “This is the bridge.”

Little me (in a very squeaky voice): “What bridge?”

“The bridge that Ichabod Crane had to cross to get away from the Headless Horseman.”

The Bridge

My little brain flooded with wonderment and dread. This was the very place that Ichabod Crane dashed across on his horse to escape the Headless Horseman. This was the last place he was known to be before disappearing forever. I clearly had no concept of geography, because we were in Wisconsin, not New England. But, none of it mattered, I felt like I was connecting with something magical and terrifying. My most vivid memory of this event is peering down below at the river running under the bridge and thinking over and over in my head. “This is it. This is the place.”

With age came the realization that The Legend of Sleepy Hollow was just a tale written by Washington Irving, and that we weren’t even close to New England. Speaking with my mother now, apparently that evening when we returned home, I cried before bed, fearing the Headless Horseman would come get me. This, I admit, I do not recall. The really vivid moment I can remember is looking over that bridge railing at the creek below in absolute belief and awe. I’m glad that I got to believe the world was filled with ghosts and magic a little while longer. I never believed in Santa Claus or the Tooth Fairy, but I sure as hell believed in the Headless Horseman.

Here is my one of my newer illustrations inspired by The Legend of Sleepy Hollow.
Headless Horseman


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