The Wilderwest was shrinking before Hiccup's eyes.
As a young boy, Hiccup's father had told him stories of a Wilderwest untouched by man. Stories of forests with trees as tall as giants with roots that dug to the very core of the Earth. Mountains that cut through the land and broke the sky with their jagged peaks. Deserts that stood as a last, arid, defense against mans' conquest. Stories so enthralling that Hiccup couldn't resist the call of adventure, and at the age of fourteen slipped from his bedroom window in the night. But now, the map was growing and his world shrinking.
Each night more and more campfires would dot the land like wildflowers in a field. The untamed wilderness that Hiccup had grown to love was being replaced with towns and farms and trading posts, leaving only tree stumps and train tracks in their wake.
The boy was on his knees, peering over a cliff's edge at one such set of tracks. Below him, the tracks cut through a mountain canyon heading from the East to towns farther and farther West. Lighting a cigarette, Hiccup was careful to avoid spilling ash onto the map that was spread out in front of him. Methodically, he dragged his pencil against the parchment, marking positions in relation to the land around him. Leaning back on his heels, he exhaled a cloud of smoke.
"I know it's been a rough few months since Berk, bud," he said, inclining his head toward his black Arabian that grazed feet away, "but I thought…Well, that we were lying low." Hiccup took another drag from his cigarette, "But Viggo is Viggo. Always planning and scheming."
A sigh, then in an impression of the gang's leader. "Just one more, Hiccup my boy. One more and then we'll have the money we need to head back West." Another sigh, his voice his own again, "To head home."
Toothless whinnied, his ears flicking in the direction of Hiccup's voice. Sensing the distress of his rider, the horse stepped closer, pushing his head against him. Casually, Hiccup rested a hand on his muzzle.
"Just gotta have faith. Right, bud?" He stroked the velvet of Toothless's nose and turned his attention back to the train tracks below him. "The train will come through here at approximately 2 a.m. Heather and the twins will already be on board, posing as passengers. The rest of the gang will catch the train as it passes through this canyon. In and out before any of Grimmel's men notice they've been hit. Of course, this all counts on you being able to catch a moving train."
The horse pounded his hooves against the ground in excitement, kicking up dust as he did so. Hiccup laughed, his voice the only sound in the late afternoon. He waved the dust away, "Good. Once I'm on the train you'll have to keep pace until I can get to the brakes."
Taking one last look at his surroundings, Hiccup folded his map and tucked it away in the inside pocket of his vest. Standing, he put his black leather hat over his auburn mop of hair to shield his eyes from the late afternoon sun and dropped his cigarette in the dirt. Pulling himself into Toothless' saddle he looked to the East in the direction of camp. "Let's get back to Raven Point, bud. We need to make sure everything is ready."
xXx
Raven Point camp was nestled in a cove hidden deep in the mountain. Surrounded on all sides by towering evergreens, the camp was secluded from even the most adventurous of passersby. At each of the entrances Viggo had posted guards, but Hiccup paid them little mind as and he and Toothless tore up the path toward the camp. Spewing dirt in all directions, Toothless skidded to a halt, Hiccup flinging himself from the saddle. At the center of the camp Viggo, Johann, and Snotlout sat around a table. Engrossed in a map and discussing the details for the heist, they paid him little mind.
Johann caught his gaze as Hiccup approached. Johann was a tall man, tanned, and always willing to tell tales of his time as a Navy Captain. However, as Hiccup got closer to the table, the familiar jovial looks were gone, replaced by a bitter scowl that covered the portion of his face his large beard didn't hide. The man turned his attention from Hiccup back to Viggo, "Why are we doing this, Viggo? I thought our plan was to lie low until we could head out West."
Anger flashed across Viggo's features, but Hiccup pretended he didn't see it. The man had been less than pleasant since the death of his brother. "We need funds, Johann. It costs money to caravan twenty people out West! Surely you of all people can understand that. "
"Of course, I can, Viggo. What I don't understand is robbing a bloody train when Flyers are breathing down our neck!"
"Everything we had, we lost in Berk! We have to earn it back if we ever want to get out of here. We rob this train and we're set." Viggo pounded his fist on the table, causing Snotlout to jump.
Hiccup cleared his throat, taking a seat beside Snotlout. "Maybe Johann is right, Viggo. The plan was to lie low. Robbing a train isn't exactly 'lying low'. It'll bring every Flyer this side of the Archipelago our way."
Viggo straightened up, putting his arms behind his back and looking down his nose at the boy. It was the look Viggo gave Hiccup when he had overstepped his place. Hiccup had received that look a number of times in the years since Viggo had brought him in, but it never failed to make him feel like that starving fishbone of a boy Viggo had found in the woods so many years ago.
"Ah, Hiccup. I was wondering when you would return. Is everything in place for tonight?
Sighing, Hiccup met Viggo's gaze, "Everything should go as planned. We can wait for the train to pass through the canyon on a nearby cliff's edge. Toothless and I scouted it just now. But Vig—"
"We ride tonight, Hiccup. Best be ready."
xXx
Thundering across the heartlands of the Archipelago, the Grimborn Gang was a formidable sight. Viggo, dressed in a red leather vest and a dark overcoat led the formation atop a large grey Turkoman he had named Skrill. A mean beast of a horse, he shared the same cold efficiency as his rider. To the right, Hiccup and Toothless kept pace. Dressed in all black, the pair were nearly invisible as they raced through the night. To the left, Johann rode dutifully, occasionally casting Hiccup glances when their horses' gallops allowed for the exchange of looks. A division was growing in the gang. Perhaps it had always existed beneath the surface, but after the Berk Massacre the group had been left beaten down and open wounds allowed for resentment to grow like an infection.
Hiccup glanced behind him where Snotlout was covering his left side. Atop his red Mustang, Hookfang, Snotlout caught Hiccup's eyes and offered a reassuring smile. Regardless of the inner politics of the Gang, Hiccup trusted in Snotlout. Though the shorter man was rash and often narcissistic, he had saved Hiccup's life more times than he cared to admit.
Behind Snotlout the three rider-less horses of Barf, Belch, and Windshear thundered along. If everything went according to plan, they would be reunited with their riders before the dawn. Bringing up the formation, Silent Sven, Hamish, and Savage rode their horses carrying the bulk of the gang's ammunition.
"Hiccup" Viggo shouted above the thunder of hoofbeats, "You'll ride down first. Deal with the engineer and the conductor in the head end. After you've stopped the train, make your way to the back train car. The twins will meet up with you. Look for anything of value. Grimmel wouldn't be sending this train through without reason." Hiccup nodded, keeping his eyes focused ahead, Toothless's reins gripped tight in his hands. "Snotlout, you and Heather will be on crowd control. Keep them quiet, and if you see anything of value, collect it. Savage, Sven, Hamish will take care of the guards. Johann and I will run point. Does everyone understand their job?"
A chorus of affirmations and Hiccup could see Viggo's smirk reach his eyes. It filled the boy with dread and sickening excitement.
Determinedly, cruelly, Viggo smirked, leaning low over his horse and urging it faster. "Well then," he said. "Let's rob a train!"
Cheers and cries of "Snotlout! Snotlout!" rose above the hoofbeats, and the Grimborn Gang set their eyes on fortune.
xXx
For the second time that day, Hiccup peered over the edge of a cliff, his forest green eyes scanning the darkness for any sign of the train. Beneath him, Toothless shuffled his hooves. Hiccup could feel the tension coiling in Toothless's muscles. The horse always grew jittery before a race.
Silence stretched the night. Then a train's whistle pierced the night. In the distance a tower of smoke billowed up into the night sky, hiding the stars from view.
"Masks up," Viggo ordered, lifting a silk handkerchief to cover the bottom half of his face. "Hiccup. Go."
Covering his face with a black cloth, Hiccup steeled his doubts and cracked the reins, shouting "Ride, bud!". Identity hidden and horse charging, Hiccup was no longer himself. In his place rode Night Fury, the infamous outlaw feared across the Wilderwest. Toothless's hooves pounded against the hard earth as he propelled himself forward like black lightning. The outlaw was only vaguely aware of the gang members that followed in his shadow as he rushed down the slope and along the tracks. Leaning low over Toothless's neck, Hiccup could see the light of the head end and then it was rushing past him and the roar of the train filled his ears as he balanced atop Toothless and leaped onto the flat train bed. Rolling with the momentum of the jump, Hiccup sprung to his feet. Beside him, Toothless had pivoted and was running parallel to the train.
Hiccup hopped the gap separating a flatbed form the front end but blocking his access to the engine room was a large container filled with the train's coal. Pulling himself up and over the lip of the container, he tumbled into the bin sending a black cloud of dust billowing up. Lungs burning, Hiccup pushed forward, careful not to jam his prosthetic between the rocks.
Attention on the steps in front of him, Hiccup had to throw himself to the ground to avoid the engineer's coal shovel connecting with his head. Coal dug sharply into his back, and although he avoided the first swing, he barely had time to raise his arms to protect his body from the second strike. The impact of metal on bone sent vibrations through his body. Disoriented, he kicked out like a drowning man, sending coal flying up in all directions. The engineer staggered back, leaning away from the coal Hiccup was kicking up.
Gunshots rang out in the air reminding Hiccup of his goals, and with newfound strength, he lunged forward. Grappling for the shovel, Hiccup kicked the engineer and as he was pushed back, Hiccup charged. The force of the charge pushed them both over the lip of the storage bin and onto the hard ground. Winded, Hiccup rolled on top of the engineer, pinning him to the ground. Hiccup's green eyes met the panic-filled engineer's.
"Stay here, will you?" Hiccup said as he removed his old, rope lasso from his belt and made quick work of tying up the engineer. More gunshots competed with the roar of the train, and Hiccup quickly closed the gap between himself and the front end's door.
The engine room felt more like a furnace than a train car, but Hiccup didn't have long to consider the heat as he found himself staring down the barrel of a shotgun.
"Up! Put yer hands up! Or I'll fill you full of bullets!" The conductor said, each word emphasized by a nudge of his shotgun.
Gods Dammit.
Hiccup raised his arms, palms out, and slowly stepped back from the man. "Sir, put the gun down. Please. Nobody needs to get hurt."
Two shots were fired.
The first from the conductor.
The second from Hiccup's revolver.
The body of the conductor fell to the ground, dead. Hiccup stepped over the body, careful to avoid getting blood on his boot from the puddle that had pooled around what remained of the corpse's head. Sparing no time for regrets, he grasped the handle of the air brake and pulled with all his might. The handle turned slowly, but he could feel the release of pressure and hear the screech of the tracks. The train came to a shuddering halt, and Hiccup allowed himself a moment to catch his breath. Then, he did as any outlaw would do: straightened his hat and whistled for his horse.
"Sorry to keep you waiting, bud" Hiccup said as he jumped into the saddle. A thin sheen of sweat covered Toothless's coarse hair, but otherwise, the horse was unbothered by the exertion. "Let's get to the back car and make sure the twins haven't set anything on fire."
Pulling the reigns, Toothless turned and loped toward the final train car. Through the train windows, Hiccup could make out the shapes of Heather and Snotlout moving through the cars and collecting belongings from the passengers. At the top of the hill, Hiccup could spy Viggo watching over the heist, a sniper rifle in his hands. Periodically, he would hear a shot and he knew Viggo was silencing a runaway.
The last train car was windowless, but Hiccup could see light pouring from a hole the twins had dynamited into the armored wall. Ruffnut was leaning out of the jagged entrance, excitedly stuffing her loot into Barf's saddlebags. On noticing Hiccup she straightened up and saluted.
"Took you long enough!"
Tuffnut poked his head out, unlit cigar dangling from his lips and arms full of bonds and coin purses. "H! My man, you have got to get in here! Grimmel is loaded!" Tuff said as he dumped goods into Belch's bags and turned his head toward Toothless. "Good job with the running, T. Saw it all from the window. Very impressive."
Hiccup rolled his eyes and hopped down from his horse who was now basking in Tuffnut's praise. Ducking his head, Hiccup stepped into the train car. "Yeah, yeah. Just get everything loaded. The sooner we're out of he— Wh-What is that!?" Hiccup gestured to the pile of bodies stacked in front of a large, mahogany desk.
"It was them or us!" Ruffnut said
"Yeah, H. They jumped us!" Tuff added.
Hiccup groaned but stepped around the bodies to search through the desk. While the twins were excellent at nabbing shiny things, they often overlooked discreet items of value. "You guys understand the higher the body count the higher the bounty, right? The more men who will be looking for us?"
"They have to catch us first," Ruffnut said.
"Like they caught Ryker back in Berk? Or Dagur?"
"That's cold, H." Tuffnut said.
Hiccup pinched the bridge of his nose and sighed. "Look, all I'm saying is that we need to be careful. The less attention we bring to ourselves the better. Just finish the jo—" the words left his throat, but never reached the air as he laid eyes on an envelope with the orange wax seal of a Singetail dragon:
Flyers Detective Agency, Department of Security & Espionage, United Archipelago.
"Whataya find?" Ruff asked leaning over his shoulder with interest.
"A treasure map?" Tuff oohed leaning over his other shoulder.
"I don't know," Hiccup mumbled, "whatever it is just might make this job worth the risks, though."
Hiccup's fingers hovered over the seal, hesitating to break the wax. Whatever was inside the envelope could potentially be incredibly lucrative to the Grimborn Gang. The information could make the asinine heist worth it. Lifting the lip of the envelope, Hiccup pulled the thick linen paper out and scanned his eyes across the page—
Bullets pounded the far side of the train car, the noise reverberating through the tiny room and making Hiccup's ears ring.
Ruff and Tuff both drew their weapons and jumped through the hole to find the source of the attack. Hiccup, sensing the situation escalating, shoved the letter into his satchel and made to follow his friends.
Ruffnut poked her head back through the hole, her eyes wide, "Hiccup, we have Flyers! They found us!"