So..A Simple Cup has given me his blessing to continue this story. I can only hope to live up to his, and your expectations. I have a deep love for both franchises and I hope I can do them justice. Just a note the first six chapters were written by A Simple Cup. Chapter 7 is the start of my chapters with guidance from Cup.

Just a heads up this version of the story will contain spoilers for Frozen 2 and How to Train Your Dragon: The Hidden World.

I hope you enjoy!

Disclaimer: I don't make millions of dollars making fantastic movies. I write FanFiction.

Chapter 1

Dread. Uselessness. Resignation.

Those were all emotions that swirled through Hiccup's head as he trudged his way back to his home. He had managed to finally slip past everyone who had been congratulating him ever since Gobber had called out to him only an hour before.

"You've done it! You've done it, Hiccup! You get to kill the Dragon!"

Woopee.

He just couldn't stand the congratulations everyone had been directing towards him. He felt dirty, being celebrated over getting chosen to kill an innocent animal. The worst came from his father though. Hiccup felt nauseous, seeing his father smiling at him with such a proud expression. He had strived to earn that look his entire life, and now that he had it, he felt nothing but misery and shame.

If anyone had really been paying attention to his demeanor, they would have seen a miserable boy trying very hard to disappear inside his clothes. Unfortunately, this, was Berk. Its inhabitants weren't exactly known for their observational skills. Only Astrid had noticed something strange, but Hiccup didn't put too much thought into it. Astrid was suspicious for the wrong reasons. Hiccup's infatuation with the girl had rapidly declined over the past couple weeks. Before he had gotten to know her, he had seen her as this warrior goddess who matched Freyja in beauty. Yet while her physical attractiveness had not diminished, he found her personality to be rather distasteful. She cared only for personal gain. Try as she may to embody the perfect Viking, Hiccup knew she had forgotten the basic fundamentals of where the Vikings drew their purpose for becoming great warriors. They fought for each other. Not themselves.

The thought made him a little bitter. Sure he screwed up a lot, but he had never intentionally harmed the village. Heck most of his inventions would work if he had been given a chance to fix the mistakes. All he had ever tried to do was help the village, and because of his different methods of doing so, he'd become "Hiccup the Useless". It didn't even matter that he was the one who forged the weapons they used to defend the village, or the fact that the fire towers had been his idea. Astrid on the other hand was about as selfish as a dragon was with its fish. Sure, she did her part helping the village during the raids, putting fires out and what not.

"Then again..." Hiccup thought, glancing around at all the brand spanking new houses with mild amusement. Maybe her 'form was sloppy' when putting out the fires.

Putting the depressing thoughts behind him, Hiccup sighed heavily as he made his way into his house and up to his room. Opening the door, he found himself standing in the door frame, looking around trying to find a method of making his troubles go away. The thought gave him pause. Was it really that easy?

Just go away.

The plan was so simple, and yet it fixed everything. Why not just leave? It isn't like he would be sorely missed. Gobber would be upset for losing his apprentice, but Hiccup knew he would be able to train another. His father would probably start an expected search party, and when they came back empty handed, start a party of a completely different nature. He was a hiccup, after all. A useless fishbone that only brought irritation and frustration to the entire village. To his own father. Leaving Berk would be a blessing for them, and who was he to give up this one chance to do something right for a change?

Steeling his resolve, Hiccup quickly gathered his journal, a couple empty sketchbooks, and all the notes regarding Toothless and the other dragon species and put them neatly into a bag. He was about to leave, before he remembered that while taking the proof of Toothless with him was necessary, he had forgotten a few other key essentials. Mainly money.

Hiccup had no intention of living off in the wilderness away from civilization. Despite how poorly he was treated here, Hiccup enjoyed the hustle and bustle of people. The satisfaction from working at a forge and making a difference really meant something to him, and he fully intended to continue the craft. In order to carry out that goal, however, he was going to need some money. Land was not a free thing outside the archipelago and depending on the kingdom, could be taxed as well. With all that in mind, Hiccup crawled under his bed and retrieved a small chest. Its contents were his entire life savings. A mixture of copper, silver and gold coins that he had gathered over the course of last eight years. Being the son of the chief has its perks, not having to pay for anything, or at least not with your own money, was certainly one of Hiccup's favorites.

Once he was satisfied that he had everything from his house that he wanted, Hiccup quietly made his way down the stairs, praying his dad wouldn't come barging into the house at this very moment. It wasn't that difficult. A decade of sneaking out from under his dad's judgmental stare to the solitude of the forest had caused him to be somewhat of a tip-toe ninja when in his home. Even if he was a klutz everywhere else he went.

When he had finally made his way to the bottom room of his house, his emotions started to get the better of him. While his resolve to leave had not weakened, he couldn't help the sharp pain of loss and sadness he felt at what he was about to do. Nevertheless, Hiccup prepared himself for what he would certainly find to be the most difficult part of his escape plan and started writing a letter to his dad.

Dear Dad,

I find myself, for the first time in my life, on what would typically be your side of a one-sided conversation.

I can't bring myself to find any joy in it.

By the time you read this I will be long gone, far away from Berk. I'm leaving Dad. And I don't intend on coming back. I have very few fond memories of this place and have decided to move to a place more accepting of my "kind". A hiccup.

I'm sorry I couldn't be the son you always wanted. Trust me, it wasn't my intention to be Hiccup the Useless. I understand your disappointment and accept it, which is why I think you'll be happy with the real intention of this letter.

I, Hiccup Horrendous Haddock III, renounce all claim to land and title, and hereby self-exile myself from the Hairy Hooligan Tribe. Give the role of chief to Snotlout, he at least wants it. Just promise me you won't force Astrid to marry him. I really don't need a pissed off shield maiden cursing me in my sleep.

Tell Gobber I love him. He was a second father to me.

Farewell,

Hiccup

Pushing back the tears that had decided to fall, Hiccup quickly folded the letter and left it on the table to be found. He felt better after writing the letter, like he was letting go of all the painful memories of the past and taking the first step to moving on with his life. Releasing a content sigh, he quickly and quietly picked up his gear and made his way out the door and into the forest towards the cove.

Entering the cove, Hiccup took one last look around at the serene oasis that he had been practically living in for the past month. It was quite possible the only place he'd miss on the island, but he supposed the reason for its place in his heart was the dragon that would be coming with him. That eased the sadness a bit.

"Toothless!" Hiccup called. "Come on out bud. You and I are taking a little vacation forever."

Before he could even react, he heard a sudden flap of wings and a solid black mass knocked him on his back. Wheezing at the sudden loss of air in his lunges, Hiccup glared at the dragon that was currently jumping up and down in excitement above him. He reminded Hiccup of an overgrown dog sometimes, waiting to play fetch.

Hiccup smirked at that, and tried to get up so he could indulge his overgrown puppy with what he wanted most. Toothless, who wasn't done yet, decided to make sure his friend knew exactly how much he meant to him and promptly licked him in the face.

"Ughhh Toothless! You KNOW that doesn't wash out!" Hiccup complained, huffing in annoyance as the dragon let out a warble that he just knew was him laughing at the boy's current state. Hiccup would have been angrier, had he not seen the look of absolute trust and friendship that seemed to radiate from the dragon's dilated, acid green eyes.

Hiccup chuckled. "Come on bud, let's fly south."

That sobered the dragon enough for Hiccup to attach his gear to him, and saddle up. Giving one last look at where his life truly began, he sighed, and patted Toothless on the head to know he was ready. The dragon didn't even hesitate, flying off into the setting sun, heading out across the sea.

Nightfall came only a few hours later and despite flying for only a short amount of time, Hiccup was exhausted. The stress and pressure he received from his village was finally starting to get to him. Deciding that they needed to stop for the night or risk crashing into the sea, Hiccup directed Toothless toward the island below.

They found a nice spot near the tree line by the coast to land where a few rather large boulders were side by side, completely blocking the night's chilly wind.

Hiccup got off and felt the early winter chill start to creep in through his furs. Rubbing his arms to keep warm, he turned to his friend.

"Guess we should get a fire going, huh bud."

The dragon just rolled his eyes and looked at him with a rather arrogant expression that clearly stated 'I don't need a fire'.

"Yea yea, you useless reptile. I should get a fire going," he replied, glaring at the dragon as he walked across the beach picking up dry pieces of driftwood, grumbling all the while.

Satisfied with the amount of gathered material, he went about getting the wood ready to light. Unfortunately, Hiccup was still, well, a hiccup, and his fire starting skills left much to be desired. Toothless, who had since laid down to sleep, opened one eye to watch as his rider struggled to create a spark. He noted that the boy was going about the process wrong, clashing the rocks together instead of rubbing them and he couldn't help but let out a warble of amusement. The laughter his eyes portrayed quickly turned to one of sympathy though, as he noticed the boy's body begin to shake from the cold. Not wanting his friend to suffer, he quickly lit the fire and gave Hiccup a gummy smile.

"Th-thanks b-bud," Hiccup said, before getting up and scratching Toothless on the chin. The dragon purred with an almost feline satisfaction and wrapped his rider with his tail, pinning him to his body and the warmth that radiated from within.

Both were quiet for a while, but when Hiccup heard the steady, drawn out breaths of the dragon behind him, he knew sleep had taken the beast. Listening to the steady beat of his friend's heart, coupled with the hypnotic sound of the oceans surf breaking across the beach, Hiccup felt completely calm for the first time in his entire life. Berk had never given him this comfort. Whether it be hiding from his cousin, or constantly trying to figure out how to prove his worth, he had never just let it all go and relaxed entirely. The feeling alone quelled any and all thoughts his brain had about returning to Berk. It was a feeling he wanted to spend the rest of his life experiencing. Letting the sounds wash over him, cleansing him of his life old fatigue and weariness, just as the waves cleansed the beach itself, Hiccup drifted off into a dreamless sleep.

Berk, The next morning

It had been an entire hour since the village had gathered at the arena to watch the chief's son take his final, and the boy hadn't shown. They had listened to Stoick give a speech about his pride towards Hiccup, had even roared in agreement, but as the time slowly ticked past, mutterings about "the Useless" and "village nuisance" started cropping up among the disgruntled villagers. Angriest of them all was none other than the chief himself, who was starting to hear the villager's harsh whispers. Trying to hide his embarrassment towards the situation, he spoke up.

"I'll go and look for him. He's probably off training and just lost track of time," he said, attempting to reassure the dubious crowd. With that temporarily taken care of, he walked out of the arena and up towards his house.

Stoick decided the best course of action was the old Viking way, and slammed the door open, shouting at the top of his lungs.

"HICCUP! GET OUT HERE! YOU HAVE A DRAGON TO KILL!"

Utter silence followed.

"What is that boy doing?" he muttered under his breath.

Undeterred, the chief made his way up the stairs and squeezed himself into his son's room, only to be shown a rather shocking image. His son's room was...clean. Alarmingly clean. Stoick could not remember the last time Hiccup's ceiling was clear of an assortment of blueprints, let alone his desk, floor, bed and walls. The sight scared him, though he wouldn't admit that to anyone but himself.

Where was his stuff? Where was his son?

With these questions racing around in his mind, he made his way back downstairs to search for more clues as to the disappearance of his son. Expecting to find evidence of him carrying on with a normal breakfast, as the Haddock's were known for leaving dishes on the table, he was met instead with a single note, sitting in front of the chief's traditional seat at the head of the table. The chief unfolded the note with slightly shaking hands and began to read, becoming paler as shock and confusion made way for guilt and sadness towards the letter's contents. By the end of it, tears were falling freely from the chiefs eyes as his actions towards his son weighed down upon him.

What have I done? Oh Hiccup...

Somewhere Far South of Berk

After an entire day of non-stop flying, the mainland of the south finally appeared upon the horizon. Hiccup had never been to the mainland, but had heard that it was a more peaceful place than the northern tribes, something he was rather looking forward to. As he started to fly over the land, he learned right away that it was just as beautiful, if not more so, than the island of Berk. A dense pinewood forest that was only broken by a single, solitary mountain. He knew other mountains dotted the land, but this one definitely seemed to be the tallest. Trees didn't grow at the top, and its peak was covered with snow.

Hiccup flew around the mountain twice before deciding to keep heading inland. He hadn't gotten very far when he spotted a small building with smoke rising out of a chimney. The teen knew he could keep going until he found a village, but Toothless was exhausted from such an extended flight, and Hiccup didn't want him getting hurt on their first full day. So he decided to land near the building and ask the owner for directions.

"Stay here bud," Hiccup said to his friend. "I'm going to see if I can find out where we are. Try to get some rest."

Toothless needed no encouragement. As soon as Hiccup had finished talking, the dragon was sound asleep. It made Hiccup feel a little bad for wearing his friend out, but he knew Toothless understood the need for his rider to find shelter. After scratching the dragon's neck, which elicited a loud hum of content from the slumbering animal, Hiccup made his way up to the house he had seen earlier. To his delight however, when he got to the building he realized it wasn't a house but a trading post! Wandering Oaken's Trading Post and Sauna to be specific, though what a sauna was, Hiccup had absolutely no idea.

A blast of warm air greeted Hiccup when he entered the store, along with an overly cheerful "Hoo Hoo" from a man who could quite possibly be bigger than Stoick the Vast.

"Don't get many travelers at night ya? Anything I can help you with?" The man he presumed was Oaken, asked.

"I'm just passing through, headed south. Do you mind telling me where I am exactly?" Hiccup asked.

"We are in Arendelle, ya? Lovely kingdom it is. Just keep going south, you'll find it, no problem." Oaken said, grinning happily at the thought of helping a newcomer.

"Arendelle huh? It's exactly where I'm headed. I don't suppose you know who I can go to purchase land outside the village?" He asked.

"Oh ya, talk to the land proprietor in the city. He takes care of all the un-owned pieces of land outside the city." Oaken replied.

"Great! Thanks," said Hiccup, heading back towards the door. An afterthought had him stopping at the entrance and taking a glance around the store. Looking back at Oaken, he asked him. "You sell any fish?"

Oaken shook his head. "No good, fish are sold closer to the coast. Too much money to ship up the mountain, ya?"

A little put out, Hiccup bid his farewell and headed out the door, a cheery "Bye bye!" following him out into the night. Tomorrow he would make his way to Arendelle. To his new home.

So..let's keep this going shall we?