John Hughes silently opened the door to his apartment, not wanting to wake his neighbors. He hung his coat and checked the calendar: April 10th, 1805. Tomorrow, Tiffany Jones would be moving to their little settlement of Turret Town, and John was determined to fall in love with her. She was 21, and the only girl from John’s generation in Turret Town he had taken any interest in, also considering every other girl had been taken. He had met her when he was just a boy, and he had felt the same way. Now that she was coming back, John was going to finish something he had started when he was just a boy.






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James Blackwood fixed his pillows, getting ready to go to bed. Tomorrow Tiffany was coming back to Turret Town after many years away. People had been telling James she was perfect for him, so he had intentions to win her love before anyone else could. He knew he could easily win her love, but he had many loves in the past that had failed. James laid down, staring at the ceiling. He was wondering how to make his first move. He closed his eyes, and he soon drifted off into a deep sleep.






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Tiffany Jones bounced up and down in the carriage, staring out the window while the world passed by. “The wilderness is beautiful, but not as beautiful as my dear old Turret Town.” Her father was nervously looking around, as if he did not trust where the driver was taking them. She gave him a questioning look, and said, “Father, what is troubling you?”

“This is the area where your mother was murdered,” he said, hanging his head.

“Oh,” Tiffany quietly said. She had never known her mother, considering she was killed when Tiffany was just a baby.

Neither Tiffany nor her father said anything until they reached Turret Town.

“Back at last,” her father said, stepping out of the carriage.

Tiffany carefully stepped out, breathing in the fresh spring breeze that was blowing. Then a young man who looked about Tiffany’s age approached her, a rose and a card in his hands.

“Hello,” she said, studying the well-dressed man.

“For you, Miss Jones,” he motioned the card and rose her way, and she carefully took them both. Then, he tipped his hat and walked away.

“That was odd,” she thought, opening the card.






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James Blackwood watched from behind a newspaper as Tiffany opened a card a strange man had just given her. He watched her gasp while she read certain parts, and then she put it in her coat pocket and walked to the other side of the carriage.

“Whatever the letter said, it must have been charming,” he thought, “Looks like I have got some competition, but that boy will just be a bug in my path to winning her love.”






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John opened the letter hung on his apartment door handle. It said:

Dear John,
I would be delighted to meet someone from my generation who seems like such a nice man. I will meet you at the Sleepy Hollow Inn for a nice dinner and a walk through Sleepy Hollow so we can really get to know each other, because I could easily do that, knowing what I know about you. Tomorrow, 8:00. Please be on time. It would be greatly appreciated.

Sincerely, Ms. Tiffany Jones.

John unlocked his apartment and strolled in, very pleased with what he had just read. He got into his pajamas and sank into his bed, mind racing with thoughts of what could, and hopefully would, happen tomorrow night. However, John forgot to predict anything bad, and he had no idea his world was about to get turned upside down.






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Tiffany slid on her shoes, the last touch to her outfit for her date with John. Getting into the carriage, she nervously sighed. John seemed like an amazing man, and she could not wait to meet him. Her thoughts were interrupted as they arrived at the Sleepy Hollow Inn. She thanked the driver and walked inside. John was already waiting at a table, and she was five minutes early.

“Hello, Ms. Jones. How are you doing this fine evening?” he asked, kissing her hand delicately.

“I’m delightful, thank you very much for asking,” she said, taking a seat across from him.






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John had thoroughly enjoyed his talk and gladly inexpensive dinner with Tiffany. He had gotten to know her very well, and he thought he was well on his way to winning her heart. He took her by the arm and led out to the path and into the woods.

“Thank you very much for dinner, and I would liked to thank you in advance for this walk,” Tiffany said as they reached the woods.

“You’re so very welcome, but it is my pleasure,” he replied, the thank you making him very happy on the inside, but he didn’t show it. The next few minutes were quiet, but John felt like he was being watched, and once he thought he heard a horse neigh.

Breaking the silence, Tiffany whispered, “Something is watching us, I just know it.”

John sighed in relief, “So you heard it, too?”

“The horse neigh?”

“Yeah,” he said, “The horse neigh.”

“Maybe we should head back, it’s starting to get real cold,” Tiffany said, glancing around.

Even though John knew it was an excuse to leave, John was happy she used it because he wanted to get out of there, too. He just nodded his head, and they turned back on the trail, unaware a headless man on a horse was a few feet behind them.






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Although Tiffany was just making up the excuse, she suddenly did feel cold. Then, she heard a hoof stomp what seemed to be close behind them. John whipped around, letting go of her arm. She turned around, too. She saw a headless man on a horse charging towards them. John grabbed her hand and started running. Tiffany was yanked behind him, almost tripping. She heard the hoofs pounding closer and closer. John was swept from his feet right beside her, but her head was pounding and she feared for her life, so she just kept running. After some time of running, she suddenly halted to a stop, turned around, and began running back for John, now fearing for his life more than her own. She reached where she last saw him, only to see a trail of blood leading into the forest. She began to feel stinging tears well up in her eyes. She wiped them away with her sleeve, and, somehow, gather the courage, followed the rail into the woods.






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John was shocked that after he was swept off his feet by the horseman, Tiffany had just continued to run. The horseman took advantage of his shock and stabbed him in the leg. He was then dragged into the woods, leaving a trail of blood behind him. He was sure the horseman would kill him, but he had just left him there. John decided to follow the trail back, and he slowly, but surely, started to make his way back on the trail of his own blood.






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Tiffany used the moonlight and the reflection of the blood against it to follow the trail. She was suddenly knocked over, and she felt her hands being tied up. The horseman swung her onto the horse, and they followed the trail much faster on the horse until they came upon John, who was slowly crawling on the trail. He looked up and tried to make an effort to stand up, but while he was on his knees, the horseman raised his sword, and then he swung down, cutting strait into John’s head. Then, Tiffany got a bag put over her head, the only image in her head was John’s limp body lying on the forest floor.

That was the last that anyone ever heard of John Hughes, and Tiffany Jones found no interest in another man until her suicide, one year later. She had dealt with the pain and nightmares of losing John until she couldn’t take it anymore. She died alone in her home; due to hanging herself on April 12th, 1806, the same day John had been murdered by the Mysterious Headless Horseman, who the rest of the town thought was James Blackwood, and indeed, it was.