Chapter 3
Hiccup decided early on that he wouldn’t stay in White Harbor for more than a week.
A week was long enough to get his bearings, to observe, to learn what he could without drawing too much attention. Long enough to move unnoticed through the crowd, but not long enough for anyone to start asking too many questions.
And in that time, he had learned a lot.
Westeros was ruled by one man, Viserys I Targaryen. One man, for an entire continent. That alone had thrown him. In Berk, his father had been chief of their small island, and even then, Stoick had carried the weight of leadership like it might break him. But here? A single king ruled over kingdoms, cities, and countless people, most of whom had likely never seen his face.
It was an absurd concept. A dangerous one. Power that distant rarely cared about the people it ruled.
Hiccup kept to the edges of the city, moving between narrow alleyways and quieter markets. He ate where the dockworkers ate, slipped coins to stable hands in exchange for stories, sat in dimly lit corners of inns, listening more than he spoke. He altered his speech when he could, adjusting the cadence of his Common, softening the sharper edges of his accent.
Slowly, people began to overlook him.
The local blacksmith let him patch a broken hinge on a harbor gate and paid him in warm bread and a heavy wool cloak. A barmaid offered him free broth after he wordlessly fixed the latch on her door. Even a grizzled old fisherman let him sit beside his fire one night after a storm rolled in, both of them staring out at the crashing waves in silence.
It wasn’t much, but it was enough.
He learned the names of nearby lords and ports, heard passing news of skirmishes in the south and unrest in the capital. No one mentioned dragons. Not once. And that, more than anything, told him how rare they truly were in this world. If people had seen them, they would be talking.
But he did hear about the king. And the princess.
The Targaryen heir, Rhaenyra, was spoken of in murmurs, some respectful, some mocking. What struck Hiccup most was how little the people agreed on anything. Some saw her as a rightful heir. Others whispered that a woman had no place on the throne. No one seemed particularly loyal. Or informed.
At first, the royal family seemed simple enough: a king, his children, a future queen. But the deeper he looked, the more tangled it became. The age gap between the princess and her younger siblings was noticeable. It didn’t take long to learn why.
The king had remarried. His second wife was younger, much younger, and her children were legitimate claimants too. That alone would have sparked unrest.
But then Hiccup learned more.
He had heard it from a potter’s apprentice, offhanded, as the man loaded clay bowls into a kiln: “Targaryens marry their kin. Keeps the blood strong.”
At first, Hiccup thought he had misheard. But the same words came from a sailor, then from a butcher’s boy, and finally from a merchant who laughed at his visible disgust.
“They’ve always done it,” the merchant had said. “Kings, queens, brothers, cousins. Keeps the dragons in the family, don’t you know?”
Hiccup had stepped away without answering, bile rising in his throat.
It wasn’t just strange. It was wrong.
He thought of his own people, of Astrid, of Fishlegs, of the way they treated dragons. Not as status symbols, not as blood-bound trophies, but as partners. As friends. Family.
The idea that someone would chain that bond to bloodlines, to ownership, boiled something hot in his chest.
That night, he returned to the cave in silence. Toothless met him with a soft nudge, sensing the storm in his mood. Hiccup didn’t speak. Just leaned into the dragon’s side and let the warmth ground him.
He didn’t sleep.
He learned more the next day, and the day after that.
In a grimy tavern tucked behind the fish markets, he listened to drunken men speak of heirs and bastards, of dragonlords and traitors. The names shifted, blurred by too much drink: Rhaenyra. Aegon. Helaena. Daemon. They were spoken like characters in a story, and yet everyone seemed certain the story was real.
The part that stayed with him wasn’t the politics. It was how casually they spoke of dragons. As if they were just another tool in a nobleman’s arsenal. As if they were swords. Siege weapons.
Not living, thinking beings.
Not companions.They weren’t riders.
They were owners.
And Hiccup hated them for it.
He’d grown up beside dragons. Toothless was more than a companion. He was family. Hiccup had built his entire life on trust, on balance, on partnership. The thought of someone chaining that bond to blood, to incest and inheritance, made his hands shake.
He didn’t care how long their dynasty had lasted.
It was wrong.
But for all his disgust, he couldn’t ignore one thing, the Targaryens were the only dragonriders left in this world.
And Hiccup needed answers.
Somewhere—across the sea, or buried in ancient archives, or maybe whispered by a rider older than the throne itself, there might be something. A clue. A way back.
Because no matter how lost he felt now, no matter how far from home he’d fallen…
He hadn’t forgotten his people.
Not for a second.
They were alive. They had to be. Astrid wouldn’t fall to some fluke of magic or physics, she was too stubborn. Too smart. His mother could outwit entire battalions and disappear before they finished blinking. And Toothless had felt it too, that tugging sensation when they crossed into this world. It hadn’t been death.
It had been displacement.
They were somewhere out there. Not gone. Not dead.
Just out of reach.
And until he knew how to find them, until he understood what kind of world this was, he couldn’t waste time chasing blind hope.
So he did what he did best: he planned. He listened. He learned.
People overlooked you if you kept your head down and your hands busy. And Hiccup had grown very good at both.
He marked places on his map at night, Skagos, White Harbor, the Bite, the Neck. Trying to overlay them with the charts burned into his memory, the flight paths he knew by heart. Nothing matched. Not a single coastline. Not a single constellation.
This wasn’t the edge of the world.
It was another one entirely.
He hated that it made sense.
And yet, despite everything, despite the way his heart clenched every time he thought of Astrid’s laugh or Fishlegs’ voice or his father’s axe hanging on the wall of their old home, he stayed focused.
Because that’s what Stoick would’ve done.
Survive. Adapt. Then go back and bring everyone home.
So he counted down the days. Tracked the shifts in the harbor. Watched the sky.
And when the week ended, he returned to Toothless with a satchel of coin, a half-burnt map, and the quiet certainty that it was time to move.
He packed quietly in the cave, Toothless already awake, wings shifting in anticipation. The dragon had grown restless, he could feel it in their bond. This place was cold, unfamiliar. It didn’t smell like home.
“I know,” Hiccup murmured, tightening a strap on his saddle. “We’re leaving. I promise.”
Toothless flicked his tail, brushing it against Hiccup’s side.
“I got what we needed,” he added, glancing south. “Now we find them.”
He didn’t have to say who.
Toothless already knew.
They saddled up as dawn broke, slipping from the cliffs in silence, wings slicing through the mist.
And as they rose higher into the morning sky, Hiccup spared one glance back toward the north.
I’ll find you, he thought.
No matter how far I have to go.The wind tugged at his cloak as he turned back toward Toothless, the early light staining the horizon with the faintest hints of pink. The chill of morning clung to the cliffs, but it was nothing compared to the storm that had settled in his chest.
He had waited long enough.
“Alright, bud, let’s get going.”
The words came out steadier than he felt. Hiccup tightened the last strap securing his bags onto Toothless’ saddle. “We have a couple of hours before morning. That should be enough time to reach Maidenpool and set up camp before sunrise.”
Toothless let out a pleased croak, shifting eagerly beside him. His tail flicked in anticipation, the energy rolling off him nearly contagious. It had been too long since they’d flown freely, too long since they’d moved with purpose.
This was the beginning of the next step. Not a wild escape, but a calculated return to action.
Hiccup adjusted his armor, slinging his bag over his shoulder before stepping out of the cave, Toothless padding along beside him. The storm from the night before had left a thick fog clinging to the ground, curling between the trees and stretching toward the city. The lights of White Harbor faded behind them as they moved, quiet, unspoken farewell.
The path ahead wasn’t clear, but it was forward.
Hiccup pulled his helmet on as he climbed into the saddle.
Toothless tensed, wings flexing, tail twitching. Hiccup could feel his excitement through their bond, and his own mirrored it.
It had been too long.
"Okay, let’s get out of he—whoa!”
Toothless shot into the sky, fast, climbing higher and higher, his wings cutting through the night air.
Hiccup laughed, pure, genuine joy spilling out of him.
The thrill of dragon riding never faded.
They climbed until the city below was nothing but a blur, then plummeted. Toothless twisted, diving at impossible speeds, cutting through clouds and mist before pulling up at the last second.
They spun, rolled, dropped, soared.
They were free.
By the time they leveled out above the clouds, Hiccup was breathless, grinning like an idiot.
“That was amazing,” he murmured, pressing a hand against Toothless’ scales.
The dragon rumbled in agreement.
They turned south, flying smoothly toward Maidenpool. The flight was long, nearly three hours, cutting through open sky, past mountains, following the curve of the land.
But something changed the further they flew.
At first, Hiccup barely noticed.
The air felt different.
Warmer than it slowly got thicker.
By the time they reached the mountains, it was sweltering.
Sweat clung to his back, soaking into his clothes, sticking to his armor. The wind, which should have offered relief, felt heavy and humid, pressing against him instead of cooling him down.
He groaned, mentally cursing himself for layering under his armor.
They needed a break.
Pulling at the straps of his cloak, Hiccup scanned below for a place to land. His eyes caught two castles nestled into the mountains, one large and imposing, the other smaller, humbler, surrounded by a tiny community.
He steered Toothless toward the forest east of the smaller castle, dipping into the trees to land in a clearing hidden from view.
The moment his boots touched the ground, Hiccup ripped off his outer layers, sighing in relief. He emptied his waterskin over his head, shuddering at the contrast before stuffing his damp clothes into a pack.
Toothless, completely unbothered, stretched lazily in the heat, purring contentedly.
Hiccup snorted. “Glad you’re enjoying this.”
Toothless ignored him, rolling onto his back.
Shaking his head, Hiccup grabbed his waterskin and started toward the creek he could hear nearby.
Toothless followed, padding behind him, eyes flicking curiously between the trees.
The cool water soothed his overheated skin as he knelt, filling his waterskin while Toothless drank beside him. The world was quiet, peaceful, just the sounds of the creek, the rustling leaves, the occasional chirp of a distant bird.
Hiccup relaxed, pulling out his map, marking where they had been. He measured the stars, adjusted the compass on his arm, and determined they were near the Bloody Gate, south of the Eyrie.
He was too distracted to notice the silence.
The lack of splashing.
Then there was a loud gasp.
Toothless let out a low, warning growl.
Hiccup’s head snapped up.
On the other side of the river stood a boy, young, frozen in fear, holding a small torch and a leather lead.
At the end of the lead was…a fat animal, shorter than a horse, with little horns and a bell clanging around its neck.
Hiccup barely had time to process it before the boy screamed.
The torch dropped into the river. Then he ran, heading straight toward the castle.
“Damn it.”
Hiccup grabbed his map, shoved it into his bag, and sprinted after him.
Toothless leaped into the air, beating his wings, jumping from tree to tree.
“Block his path!”
Hiccup was fast, but the boy had desperation on his side.
The kid sprinted through the trees, tripping over roots but not slowing down. His bare feet slapped against the dirt, one hand clutching the lead of his animal, the other wildly swinging as he ran. The bell around the creature’s neck jangled with every panicked step.
Hiccup weaved through the trees, his longer strides closing the distance. Above, Toothless was already ahead, darting through the branches, his black scales almost invisible against the night.
Hiccup saw the exact moment the boy realized he was trapped.
The kid skidded to a stop, nearly falling backwards as he looked up and saw Toothless crouched on the path ahead.
The dragon’s green eyes glowed in the dark, pupils slit in warning, a low rumble vibrating from his chest. His tail flicked, wings half-spread, blocking the boy’s path.
The kid froze, his hands clenching the lead of his animal as his breath came in short, panicked gasps.
Hiccup broke through the trees a second later, slowing as he approached.
The boy’s head snapped toward him. He weighed his options, eyes flickering between Toothless and Hiccup, his body coiled like a startled animal.
Hiccup lifted his hands, palms up, taking slow, careful steps.
“Hey—”
The boy collapsed to his knees.
Hiccup startled, stopping mid-step.
The boy bowed his head, hands clasped together, shaking as he pleaded, “Please, milord—do not kill me! I beg of you, show mercy!”
Hiccup stared.
“What?—I—” His brain stalled.
“I am only a farmer’s hand! I’ve no coin, only this cow! But I beg you—please do not kill me!”
The boy was crying now, full sobs shaking his small frame, his head still bowed low, voice choked and desperate.
Hiccup’s stomach twisted.
He had never had someone beg for their life in front of him before.
He took a step back, horrified. “WHAT?—I’m not going to kill you!”
But the boy wasn’t listening, still sobbing, his words turning into unintelligible, panicked pleas.
Hiccup sighed sharply, dragging a hand down his face.
This was… a disaster.
Rolling his eyes, he strode forward and grabbed the boy’s shoulders, hauling him upright.
The kid yelped, his feet dangling off the ground as Hiccup lifted him effortlessly.
Hiccup locked eyes with him, voice firm but not unkind.
“I am NOT going to kill you.”
The kid blinked rapidly, face frozen in shock.
Hiccup held his gaze for another second before gently setting him back on his feet.
The moment his boots hit the dirt, the boy scrambled backwards, too fast, his foot catching on a root. He tripped, sprawling onto the ground.
Hiccup sighed again, pinching the bridge of his nose.
This was exhausting.
Crouching down, he extended a hand. The boy hesitated, staring at it as if it were a trick. Then, cautiously, he took it.
Hiccup easily pulled him upright, letting go once the boy had his balance.
Hiccup got a better look at the boy after he’d washed off in the river.
He was young, twelve, maybe thirteen, with tanned skin and dark brown hair that curled slightly when wet. His eyes were light brown, wide and expressive, and his face was scattered with freckles. A thin scar traced the edge of his brow, likely the result of some accident during work. His clothes were rough, the seams stretched and patched in places, and his frame was lean from too much labor and too little food.
He still looked nervous, but less terrified.
Hiccup handed him a small waterskin and settled down beside him on the riverbank, letting the silence settle between them for a few seconds before gently asking, “What’s your name?”
The boy took a tiny sip of water, still clutching the flask like it might disappear.
“…Ben.”
Hiccup smiled softly. “Ben is a nice name.”
Ben’s shoulders eased slightly, his grip loosening. “You really think so?”
“Oh, I know so.” Hiccup sighed dramatically, placing a hand on his chest. “Far better than my name. Hiccup was not one of my father’s greater ideas.”
Ben giggled, and for the first time, the fear slipped from his face, replaced by something brighter. Something younger.
“Hiccup… Targaryen? What a strange name.” he said with a huff, tilting his head, still smilinguntil the smile vanished.
His face drained of color.
He jerked back, suddenly pale, eyes going wide with horror. “Apologies, milord! Or—or my prince! I meant no offense! I swear, Hiccup Targaryen is a fine name! It was a jest—I only meant—”
“Whoa, whoa—calm down, kid.”
Ben’s panicked words tumbled to a stop. He stared at Hiccup with wild eyes, his whole body tense again.
Hiccup exhaled, running a hand through his hair. “You’re not in trouble. And I’m not a Targaryen.”
Ben blinked. “You’re not?”
“Nope.” Hiccup smirked, then gestured toward Toothless, who was perched contentedly on a rock, fishing with his tail. “And that’s Toothless.”
Toothless perked up at his name, head snapping toward them with a proud glint in his eye and a freshly caught fish dangling from his mouth.
Ben gawked. There was awe in his stare, but confusion too, like something didn’t quite add up.
“But… I thought only Targaryens were allowed to own dragons.”
Hiccup snorted, an involuntary, startled sound. That was, without a doubt, the funniest thing he’d heard all week.
He laughed, loud and bright, then immediately caught himself when he saw Ben’s wounded expression.
“Ah—no, no, I wasn’t laughing at you.” He raised his hands apologetically. “I just meant… you don’t own a dragon.”
He looked back at Toothless, his expression softening. “Dragons aren’t things you keep. They’re wild, powerful, smart. If you earn their trust, they’ll give you everything. But only if.”
Ben turned back to Toothless, watching the dragon with something almost reverent in his eyes.
“Can… anyone have a dragon?” he asked quietly.
Hiccup hesitated, then reached over and ruffled the kid’s hair. “If the dragon finds you worthy enough to ride them… then yeah.”
Ben grinned, a bright, blinding smile that stretched across his entire face.
“Well,” Hiccup added, eyes twinkling, “maybe when I reach King’s Landing, I’ll bring back a dragon friend for you.”
Ben’s smile grew impossibly wider, his whole face glowing.
“Is that where you’re heading, milord? To King’s Landing?”
Hiccup opened his mouth to answer, but Ben’s expression shifted again—his eyes darkened, voice dropping low.
“You best be careful, milord,” he warned. “The dragons strike when the sheep are blind.”
The words hit like a stone skipping across calm water.
Hiccup’s brow furrowed. “What does that mean?”
But Ben didn’t answer. Just as quickly as it came, the seriousness vanished, replaced with a sudden, bright grin.
“But you’re a dragon too!” he chirped. “So maybe you’ll be fine!”
Hiccup blinked, caught completely off guard. “Okay, wow—you are confusing.”
Ben just beamed.
Despite the brief calm, Ben insisted Hiccup leave quickly.
“They burn those who show disrespect,” he’d said, waving his hands urgently. Hiccup frowned at that.
But the boy didn't seem to notice pushing him towards Toothless. “I must get going anyhow, farmer Hugh will whip me if I don't get Bessy back in time.” Ben smiled at Hiccup as he stepped a few paces back waiting for Hiccup to leave.
Hiccup sighed, glancing at Toothless who was already crouched, waiting.
“Alright, alright, we’re going.”
He climbed into the saddle, adjusting his gear with practiced ease. Before they took off, he reached into his pouch and pulled out a small gold coin.
He tossed it to Ben, who caught it with both hands, eyes wide.
“Keep that,” Hiccup said. “A sign of our friendship.”
Ben clutched the coin to his chest like it was a treasure.
Hiccup gave him a small nod, pulled his helmet down, and leaned forward.
“Toothless—go.”
The dragon launched upward in one smooth motion, wings beating powerfully as they lifted off the forest floor. Ben grew smaller and smaller below them, a dot between the trees, still waving with one hand and holding the coin tightly in the other.
The sky opened up before them, and with it, he road to King’s Landing.