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Downing the Dragon.
As he set the Mangler - boy, he really did need to come up with more creative names for the things he came out with -all Hiccup needed to really do at this point was to just wait for any sign of the Night Fury. It was hard; while the villagers had the benefit of being able to track the dragons raiding the village by the distinctive shapes of the dragons, and their fires, the Night Fury was something really unknown.
The only way to track it was by listening, and so as he looked around tensely for the Night Fury to appear, Hiccup hoped this worked; after years and years of being mocked by either his father or one of the other villagers, well he'd just about had enough of his life as the village runt.
It was time for all of that to change.
Looking around for the Night Fury, Hiccup listened while he held onto the controls for the bola thrower.
All he could make out were either the echoes of the real cries of the dragons attacking Berk, and it was hard if not impossible for him to pick out what was real and what was nothing more than a straightforward echo, but the Night Fury's sound was extremely distinctive. As his eyes darted from left to right, from one angle to the next, Hiccup wondered if he was aiming just a little too high. It was only a small spark of a question, fixed in the back of his mind, but it was there, and try as Hiccup might he could hear this little voice getting louder.
But as long as the little voice in the back of his mind arguing with him about killing a dragon did not distract him from his task, well it could be easily ignored.
Sure, while the killing of a Night Fury would finally shut up everyone who called him a runt and shunned him with disgust, Hiccup knew the Mangler could easily be used on some of the more common breeds of dragon. Unfortunately, as the little accident with the Mangler accidentally being triggered and throwing a bola at one of the Vikings near Gobber's forge had proven, it was dangerous. Okay, sure coming up here was a risk, but if it got results then it was worthwhile. At the same time, he had time to think about this.
Hiccup hoped that he caught the Night Fury, and even if he couldn't catch the elusive dragon, there were enough bolas in the magazine of the weapon to knock out a dozen other dragons. If he could down other dragons besides the Night Fury then his respect would skyrocket and he'd get the kind of life he felt he deserved. But the truth was Hiccup really wanted to cement people's trust and respect in him, and the only way he could do that was to go after the elusive Night Fury, a dragon so legendary nobody knew about them.
The sudden shrieking in the air made Hiccup tense and peer through the targeting ring while he tried to trace the sound as it flew overhead… only for a bolt of bright purple fire to explode in front of him. As he squinted at the white blinding light, Hiccup couldn't believe his luck when he pulled the trigger, only to cry out when the force of the Mangler firing a bola sent him flying.
"Aah!" Hiccup cried out as he painfully made contact with the ground, but he was only shaken and not seriously hurt. That was a relief.
But as he got back to his feet, the sound of shrieking in the air, a cry of sudden pain echoed down to him. Hiccup looked up in the air, following the sounds of the roars as it passed by, and he swore he could see something long and thin fall out of the sky. A grin rose to Hiccup's face as he heard the Night Fury crash in the woods close to where he was.
"Oh, I hit it! Yes, I hit it!" Hiccup yelled, dancing a brief little jig while he looked around, hoping to see someone near him. "Did anyone see it?"
Later when Hiccup looked back on this moment (feeling shame as he did), he would be forever debating with himself whether the Monstrous Nightmare which suddenly appeared out of nowhere over the edge of the cliff had seen what he had done, or if it was just taking advantage of the opportunity to flash-fry him alive.
The growl of something big crushing the Mangler to pieces.
Hiccup turned and right in front of him with a distance of just mere inches, was a Monstrous Nightmare. "Except you."
As he raced down into the village, Hiccup had no idea what he had just done would have terrific consequences which would change his life forever. In the morning, his ears ringing with his father telling him bluntly he was no dragon killer, he would go out into the forest in the hopes of proving his father wrong…. Only to prove his father right, when he had the wounded Night Fury completely at his mercy, and he refused to kill the dragon when he realised it was terrified of death.
After sparing the dragon, Hiccup would realise everything the Vikings had told him about dragons was wrong.
The dragons were supposedly emotionless demons… so what was the fear in the Night Fury's face?
Hiccup was completely at the dragons' mercy - Gobber himself would say during the first lesson in Dragon's Training dragons always went for the kill, so why was he still alive?
After a while, Hiccup would ask himself why the dragons even came after the Vikings for food, after seeing how Toothless, the Night Fury hunted, and how other dragons went for food, what was going on? Why did the dragons raid the Viking tribes? It only then did he realise something else was going on.
Once he was over his fear, Hiccup had no way of knowing he would tame the dragon and earn its trust in him before realising because the Night Fury was crippled and was unable to fly with one of its tail fins torn away by the bola, it couldn't fly without a replacement… only one that Hiccup himself could control.
Later, he would give the Night Fury a name.
Toothless.
Together, he and Toothless would both become a team. Together once they had learnt to rely on and trust each other in the air, they would both end the Dragon War and defeat the Dragon Queen.