Shadows of the Headless Horseman

Submitted into Contest #169 in response to: Write a murder story where the murder weapon is the knife used to carve a pumpkin.... view prompt


Suspense Thriller Adventure

As a child, I read the story, “The Legend of Sleepy Hollow” and thought the town was only a figment of Washington Irving’s imagination. That was until I moved there. How I happened to end up in Sleepy Hollow is another story, but to put it simply, I was unemployed and was offered a job there. Being from Albany, New York, I did have far to travel. I just had to head down Interstate 87, head east across the Hudson River, and voila! I was there.

Now you may think I was offered a glamorous job, such as a bank vice president, or a member of the board of a major company, but that would be far from the truth. In fact, I assumed the position as an IT tech for a mom-and-pop computer store. When Randy, the owner of The Computer Box learned my computer skills went far beyond working on smartphones, he hired me on the spot. Secured in my job, I rented a small apartment close to the legendary church and cemetery.

As I look out my window, I can only imagine the forest laid in the valley and hills beyond two-hundred-fifty years ago, for now all that remains are endless houses and roads leading beyond. All visions of the Sleepy Hollow I had as a child were now eradicated. But that didn’t cool my curiosity about the headless horseman himself. Was there any truth to his story or was it a complete fantasy? So, wanting to satisfy my curiosity, I decided to ask the town’s people themselves.

Unfamiliar with the town layout or who’s who in the village, I decided to go to where all questions can be answered, and low and behold, my destination was only two-hundred feet in front of me. “Joe’s Tavern.”

When I walked in, I was amazed at how many people were there. It was 2 P.M. and it was standing room only. The patrons were broken off into small groups sitting at the bar as well as tables, and all were discussing different topics. As I passed each table, I could listen in to what they were talking about. Most were talking about football, while others were talking about politics. Being near the end of October, these two subjects were the main courses, but as for me I wanted the dessert. And there, in the back corner of the tavern, I found it. Four people were sitting at a table talking about the soon to arrive tourists, hoping to get a glimpse of the headless horseman. So, I ordered a beer at the bar and sat myself down next to them.

After they gave me a funny look, they introduced themselves as Stu, Gordy, Will, and Walt. Then they continued their conversation and pretended I wasn’t there. After Stu took a sip of his beer, he spoke out to anyone who would listen. “I’m telling you those damn tourists got it all wrong. They listen to that Disney crap and think it all happens on Halloween night.”

Walt interrupted. “What’s wrong with Disney’s version? I thought it was quite entertaining. I let the grand kids watch it every year.”

“That ain’t the point,” shouted Stu. “It’s just plain wrong. I should know. I’ve seen the horseman myself.”

“Yeah, yeah,” Gordy interjected. “You tell us every chance you get.”

My curiosity just turned up a notch. Was there actually some truth behind the story or was Stu a victim to an elaborate hoax? There was one way to find out. After paying to their next round, I dared to ask, “So, tell me Stu, what’s your story?”

Warmed by the cool beverage a bought him, he began, “It was a dark stormy night.” As his companions groaned at his overused opening, he resumed, “I was doing some late-night repairs at the church. A couple of light switches weren’t working well and needed replacing. I don’t know how many times I informed the pastor he really needs to redo the entire wiring system, but does he listen to me? No!”

Walt threw a drink stirrer at Stu. “Focus, old man! Get back to the story, before you bore us to death with your useless blathering.”

Stu was unphased by Walt’s barb. “Take it easy, buddy. I was getting there.” He took a deep breath and continued. “Anyways, I packed it up for the night and headed home. As I got past the cemetery, a flash of lightning lit the way before me, and I’ll never forget that horrid silhouette I saw on the hilltop. It was a man, mounted on a horse. I could see him as clearly as I see you now. But where his head should be, was nothing, and cradled in his left arm was a jack-o-lantern, with its face staring at me. Someway, somehow, there was a connection between that crave out pumpkin and the man, for suddenly the horse reared up and charged towards me, carrying that headless monstrosity my way. I tell you I was scared shitless. I turned my ass around and ran like hell back to the church. When I got inside, I bolted the door and pressed all my weight against it, praying it would hold. A moment later, I heard the horse galloping towards me louder and louder. And then, nothing. It was as if he was never there. Well, I’ll tell you there was no way I was going out then, so I hunkered down in one of the pews and had a sleepless night. When the sun came up, I gathered up my courage and went home. That, my friend, is my story.”

And quite a story it was. Still, I wasn’t convinced of its validity, so I asked, “Is there anyone who can back up your story? I mean, I want to believe you. You understand, I hope.”

He looked at me strangely, as he took another sip of his beer. “There is another,” he began. “Emily DeLano. She lives in the ugly purple Victorian house at the end of the street. I’m afraid you can’t miss it.”

“So, she can back up your story,” I asked.

“Nah, she doesn’t have to. She has plenty of her own. Also claims she’s a direct relative of Katrina Van Tassel. That was Ichabod Crane’s wannabe girlfriend if you don’t recall.”

No, I didn’t recall, but I knew where I was going next. So, I finished my beer and said farewell. Next stop, Emily DeLano’s.

Stu wasn’t kidding when he said the house was ugly. If I didn’t know better, I’d say someone splashed bright purple paint on the house and spread it around with a broom. Rain gutters were hanging loose in various places and the shingles were crying for repair. Though the appearance of the house was quite abhorring, I made my way to the front door and knocked loudly.

Half expecting an old crone to answer the door, I was taken back when the face of an attractive woman appeared instead. Being fair skinned, her blue eyes accented her blonde hair and seem close to my own age. When she first laid eyes on me, I thought to myself, I should have taken a shower and dressed better. After all first impressions are important, especially if I really want to get close to someone. But I didn’t and now I had an uphill battle to present myself.

Before I could make a bigger fool of myself, Emily saved me with her words. “The way you dress tells me you’re not a salesman. So, how can I help you?”

“I’ve heard a rumor you’ve seen the headless horseman. If you have, I was wondering if you could tell me about your experience?”

The edge of her lips lifted, as her eyes lit up. “You seem safe enough to me. come inside.”

A moment later, I found myself sitting next to Emily in the living room sipping on tea. After what seemed like an eternity, she uttered, “It was eight years ago when I first saw him. I’ll never forget the night. The full moon revealed its full majesty through a cloudless night. I was walking home from church after choir practice. Being the weather was fair for October, I decided to take the long way home and walked around the perimeter of the cemetery. I wasn’t even halfway around when he charged towards me on his cursed horse. Being far from town and out of earshot from anyone, I was powerless to do anything. So, I bravely stood there and awaited my fate.

“Closer he came and as he did so, he lifted his jack o lantern head from his shoulders and prepared to fling it at me. But when he pulled up beside me, he stopped, as if frozen in time. Slowly he placed the pumpkin back on his shoulders and if his triangular cut eyes could show emotion, it would be as if he reunited with a lost love. Minutes passed before he finally pulled on his stirrups and galloped away. Free of my peril, I ran to the safety of my home.

“I thought of reporting what I have seen to the police, but then decided not to. They would have treated me like a nutcase, and I couldn’t have blamed them. Still, rumors of my experience bounced from ear to ear, and I became part of the local legend.

Since that night, I had time to think about what had happened and could only produce one theory. The Hessian soldier who chased Ichabod Crane succeeded in freeing himself from his curse, and it is now Ichabod Crane who is riding those dreaded nights. That’s why he didn’t harm me. Somehow, he saw Katrina Van Tassel when he gazed at me. In case you hadn’t heard, she was my grandmother many times removed.”

Anyways, since then whenever there’s a full moon in October, I find myself looking out my windows towards the cemetery, searching for Ichabod’s tortured soul, and I swear to you, I see him on the horizon, returning my gaze. Tonight, I’ll be doing the same”

My heart skipped a beat when I heard her story. Not from hearing her experience, but in learning the horseman may appear tonight. If somehow, I could get a picture of him, I’d have proof of his existence and become famous overnight. All I must do is survive the night. I had work to do, so I thanked Emily for her time and tea, and returned to my apartment.

Before my front door closed, I was scavenging through some unpacked boxes hunting for supplies. First, I found my digital camera. After checking the power level, I put it to the side and continued to dig. Next, I found my cue stick, a roll of duct tape, and finally, a carving knife. I had more to do than take a picture. I also had to protect myself. So, using the cue stick, tape, and knife, I constructed a makeshift sword. Finally, I found my running shoes. If all else failed, I wanted to give myself a chance to flee. Now there was nothing for me to do but wait.

As the sun began to set, I found myself standing between the church and the cemetery, waiting for what might come. As the blue of the horizon faded to dark, my fears and apprehensions grew, like the shadows surrounding me. As the stars came into view, I was tempted to return home, ready to dismiss the horseman as fantasy, but then I said to myself, “If it’s a fantasy, why am I afraid?” So, I stayed ready to seek the truth.

Shortly after the sun set, the moon rose illuminating my surroundings, the church to my back, and the cemetery to my right. Then, from my left, I heard a horse whinnying and hoof steps galloping towards me. The horseman has found me and was in pursuit. Quickly, I balanced my makeshift sword on my shoulder and aimed my camera towards the horseman. As he came into view, he lifted his jack-o-lantern head and aimed it towards me. I snapped the camera shutter several times, then threw it to the ground. Sweat poured off me as the realization I was facing death came over me. There was no sense in trying to run away, for he was too close. The only option open to me was to stand and fight. Brandishing my sword, I was ready to attack.

Closer and closer he came to me. Forty feet, then thirty. Twenty feet turned to ten. The moment he began to hurl his pumpkin head towards me, I swung my sword with all my might. As my sword passed through where the rider sat, there was no resistance, as if I were slicing through air. But when my sword struck the jack-o-lantern, there was a loud thud as the sword sliced the pumpkin in two. As the two pieces of the jack-o-lantern struck the ground I could hear a voice sighing, “At last, I’m free.”

Then the vision of the rider as well as the horse vanished before my eyes, leaving nothing but a memory of the night’s escapade. Brushing the dirt off my clothes, I picked up the camera and returned home, but before I packed it up for the night, I had to view the evidence. I uploaded the pictures to my computer and looked to see what I had. But there was no way I could hold my disappointment when I saw them. Visible were the houses in the distance, as well as the skyline, but as for the horseman, it was as if he never existed.

That’s it, I thought. I’m the new kid in town, so who’s going to believe me? The last thing I need to do is end up like Emily DeLano and be the laughingstock in town.

Then I thought about Emily and her purple house. She said she would be watching for him. Who knows? She might have witnessed what had happened. I could call on her and talk about it over a cup of tea and see. I could think of a lot of things worse than that. Still, I wonder. Did I lift the curse of the headless horseman or not? We’ll see next year.

October 26, 2022 20:10

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Howard Seeley
03:28 Oct 29, 2022

And you thought it was just a fairy tale. Enjoy!


Andrea Doig
20:11 Nov 05, 2022

Interesting story Howard! I wonder if he did set the headless horseman free… I think he did… but something tells me that he and Emily’s story is not over yet 😉. I picked up a few grammar and language (editing) errors… but those are easily fixable. Thanks for sharing and keep on writing 😊


Howard Seeley
02:45 Nov 06, 2022

Well, we'll just have to wait and see! Thanks for the comment.


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