"What in God's name happened to you?" Caretaker asked, bewildered and thoroughly...curious? He should have been fearful. A more sane man would. But Caretaker assumed himself to have gone mad. Perhaps he felt himself within a strange dream, or a dark fairytale.
Because standing opposite him hunched the headless form of the previous watcher--the one appointed to guard the only bridge in and out of Sleepy Hollow.
The figure's right hand clutched a burlap sack, blood dripping from it's bottom. Caretaker noticed the uneven cutting to the hapless being's neck.
"Were you ambushed?" he asked, daring to step closer.
Without a word, the figure reached into the burlap sack. Clutching the hair, they pulled their severed head free. With laboring steps, they stumbled closer, holding the head up so Caretaker could look.
The expression frozen on their severed head confused Caretaker.
Their listless eyes held a look of both anger and...resignation? Did they know their attacker? Is that how their attacker was able to get close enough to sever their head?
"Who did this to you?" Caretaker whispered, lifting his gaze to the hackneyed neck. "Do you know?"
The figure inclined their shoulders to him, as if to say they did.
"Are they still living?"
They dropped their head to the ground as they stumbled back. Caretaker caught their arm before they could fall completely.
"I'm sorry," as if that could heal anything. "...where are they now?"
Clutching Caretaker's arm, they slowly pointed, not in the direction of the town, but in the direction of the far bog--a treacherous place of filthy vermin and sorcerous fugitives.
That explained why this poor wretch still lived.
Leaning down, Caretaker collected the discarded head. As he shouldered the headless creature against him, he set his gaze towards the bog.
"What say we even the odds, hm?"
With an incline of the shoulders, the headless being agreed. From the depths of the wood, Caretaker heard the sound of thundering hooves. Before he could speak, a fierce stallion with fire eyes and fog for his mane approached them. Grasping the reins, the headless watcher mounted the stead. Then they extended their hand to Caretaker.
At that moment, Caretaker wondered if perhaps this was a foolish idea. But the madness had already begun when this poor wretch lost their head. Perhaps Caretaker had, as well.
He took the extended hand, hoisting himself up behind the rider. With a dig of the stirrups, the headless rider spurred the stallion towards the bog.
And as the night surrounded them in shadow, Caretaker could swear that the severed head he held now wore a smile.