1 - 20 of 6,528 Works in Toothless (How to Train Your Dragon)
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Berk and the Dragon Hunters are locked in a war Berk cannot hope to sustain.
When a fall leaves Hiccup vulnerable, Viggo Grimborn sees an opportunity:
not only to win, but to claim something he never should have wanted.
A union born not of peace, but of desperation… and of a desire neither of them dares to name.
War made them enemies, and desire could turn them into something far more dangerous. -
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Even with Drago gone, the aftermath of his reign opens old wounds. Leaving Zyrah, the unwanted child of two of Drago’s former hunters, to uncover her history. And her beloved female Night Fury brings Toothless to his roots.
Series
- Part 1 of In Wind and Waves Saga
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The Hall Boy by booksandfairytales111, P_Artsypants
Fandoms: How to Train Your Dragon (Animated Movies)
11 Jun 2026
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As a lowly servant in the castle, Hall Boy Hiccup Haddock has no chance with Princess Astrid. Still, he decides one night to write a letter he doesn't intend to send, pouring his heart out. His rambunctious dragon friends take it upon themselves to deliver the letter, and thus, a beautiful friendship is born.
Will the pen pals meet and reveal their identities at the Princess's ball? Or will the Hall Boy's rotten uncle and cousins ruin it all?
An archive of a RP thread with DragonMasterHiccup on Tumblr.
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Messengers of the Gods: Race to the Edge (S4) by CourtesyTrefflin, RivanaRita, TiranaSorki
Fandoms: How to Train Your Dragon (Animated Movies), How to Train Your Dragon - All Media Types, DreamWorks Dragons (Cartoon)
11 Jun 2026
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The war with the dragon hunters is escalating, and Hiccup finds himself perhaps with a few tentative new allies, but the dangers are no less all the way around.
Series
- Part 7 of Messengers of the Gods
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How To accept the fact that- holy shit I’m a dad now WHAT THE FUCK by Jinxx_00x
Fandoms: How to Train Your Dragon (Animated Movies)
11 Jun 2026
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After impulsively adopting the child of a dragon hunter he killed, Hiccup now has to deal with the aftermath. Confronting the fact that he now has a child.
A child who used to live with and help a dragon hunter… while he hasn’t had any proper human interaction since Berk.
That could never go wrong.
Or~
Hiccup is an emotional mess and doesn’t know how to handle his new child and Skadi doesn’t know how to handle friendly dragons
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My Blood is Water by P_Artsypants
Fandoms: How to Train Your Dragon (Animated Movies), DreamWorks Dragons (Cartoon)
11 Jun 2026
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Fishing and sailing meant everything to the village of Berk. Hiccup Haddock, son of the chief, unfortunately has an allergy to seawater, and is not allowed on the boats. This makes him a bit of an outcast. But when he accidentally takes a dip, he finds out the real reason his father has been so secretive about his dubious origins.
He thought it was hard enough keeping cool around his crush and getting approval from his fellow tribesmen, but no. Now he has a fish tail to worry about, of all things.
Series
- Part 8 of Hiccup Haddock is a Weird Creature™
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For Whatever’s to Come and Wherever This Goes by Vespera21
Fandoms: How to Train Your Dragon (Animated Movies)
11 Jun 2026
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Hiccup is joined by his family, friends, and flock to start a new life away from Berk. Just because they’ve left their old lives behind, though, does not mean that everything will be easy. From facing foes to finding allies, life has a way of always keeping Hiccup on his toes, but with those he loves at his side, he’ll made it through, even when faced with a surprise or two that are beyond belief.
Series
- Part 4 of Somebody to You
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a drag path etched in the surface (as evidence I left there on purpose) by grim_hawkins
Fandoms: How to Train Your Dragon (Animated Movies), Rise of the Guardians (2012)
11 Jun 2026
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Stoick tells him that his heart isn’t where it’s supposed to be.
Hiccup doesn’t even know what that means.He is terrified of becoming a chief.
He starts to suspect where his heart really is, though.
It’s with Toothless. It’s with the skies.It’s with a chaotic winter spirit he found on a godforsaken stretch of land in the middle of the ocean, though he is not ready to admit it anytime soon.
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Hiccup and Astrid spend a pleasant day alone with their dragons, thinking about their other half.
- Language:
- English
- Words:
- 2,079
- Chapters:
- 2/2
- Hits:
- 15
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The Paradigm by FrostedDreams1234
Fandoms: How to Train Your Dragon (Animated Movies), The Avengers (Marvel Movies)
11 Jun 2026
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Strange happenings have been occurring throughout the island of Berk. A mysterious and new dragon has appeared, along with an unknown force that sends the Dragon Riders into a completely different world. The modern world.
Things go from bad to worse when Hiccup, his friends and the dragons are all separated in the process. And worst of all, they are also caught in the middle of an investigation run by an agency known as SHIELD.
Their only solace? A teenager from the modern world who is somehow unlucky enough to get dragged into their mess, along with the very dragon they had been tracking.
Originally posted on Fanfiction .net Dec 1, 2015 under the username Story of Your Life; it has been merged into a single account and rewritten.
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Hiccup tried to shoot down a nightfury, but ends up with more then he had bargained for
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Dumping ground for my httyd drabbles--mostly hiccstrid, mostly lighthearted
Chapter 36: Another -
The Snotman and His Weird Protégé by DapperAxol
Fandoms: How to Train Your Dragon (Animated Movies), How to Train Your Dragon (2025)
11 Jun 2026
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Snotlout was proud of himself. Why wouldn’t he be? He was strong; strong enough to know he was the best up-and-coming viking, like, ever. It was obvious to anyone with eyes. And wasn't stupid.
That was knowledge he carried around every day, reminded of every time someone else messed up, and would boast gleefully at all times. Because no matter what happened, he was the best. No wimp-faced, snarky, annoying cousin could possibly ruin that for him. That couldn’t--wouldn’t--happen. But…
Just how did said cousin keep taking down all the dragons before Snotlout really got a chance? What in the Hel had Hiccup been hiding?
…How did Snotlout end up way too deep in trouble, right along with him?
(TLDR;
Essentially a What If? of Snotlout being the first one to discover Toothless, instead of Astrid. What if, instead of writing Hiccup's success off as some crazy stroke of luck like most people did in the movie instead of become suspicious, Snotlout just...literally couldn't believe Hiccup was good at something?Featuring RTTE characterization because it is hands-down the best. (Fight me.) Also yes, new summary! Yay!)
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The Girl and Her Night Fury - Riders of Berk by Katherine97
Fandoms: How to Train Your Dragon (Animated Movies)
11 Jun 2026
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The fourth book of the Girl and Her Night Fury series:
Berk, once a village plagued by dragon attacks, is now a haven where dragons and Vikings live in harmony, thanks to the heroic efforts of Hiccup, the Chief's daughter, and her loyal dragon, Toothless. Despite the peace in Berk, Hiccup, Toothless, and their friends face strange new dragons and unexpected dangers that threaten the Viking Villagers.Series
- Part 4 of How to Train Your Dragon
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Thousand of years ago many dragons fled their homeland, a tyrant had killed their king and taken over. Killing for sport and destroying everything. His reign was endless. Until two brothers appeared.
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Something Old, Something New by Magmashift
Fandoms: How to Train Your Dragon (Animated Movies)
11 Jun 2026
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It's been a year after Drago's defeat and Berk has never been happier. Except with Berk now turned into a sanctuary, they've become the target of a widely acclaimed Night Fury hunter who wants to put an end to the era of dragons and Vikings living in peace. So with an unexpected ally, Hiccup has to decide what kind of chief he wants to be. One who keeps up the traditions practiced for generations before him? Or one who brings his people into the future?
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What would have happened if Hiccup didn’t go after Astrid after she found out about Toothless?
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A Wingwatcher's Guide to Training Dragons by Ringetteskater888
Fandoms: How to Train Your Dragon (Animated Movies), Wings of Fire - Tui T. Sutherland
10 Jun 2026
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What if How to Train Your Dragon took place in the world of Wings of Fire?
Hiccup Haddock lives in the Indestructible City with his father, the Chief of Defense, Stoick the Vast.
Desperate to prove himself, Hiccup attempts one of the most impressive (and dangerous) of feats: Killing a dragon.
But when he looks into the eye of the dragon he shot down, he finds himself wondering if he can truly go through with killing a dragon.Sharpteeth is a runaway from the NightWing's volcanic island. After being shot down (and spared) by a scavenger, he finds himself stuck in a cove, with seemingly no way out, and a strange little creature bothering him every now and then.
As the pair begin to bond with each other, they slowly being to realize that their worlds are bigger than they thought, and perhaps humans and dragons aren't so different from each other after all.
I will be mostly following the movie's plot at the beginning, with changes to fit the story into Wings of Fire. Eventually it'll split off from the movie's plot and become it's own thing. I have some fun ideas for the future.
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Lines in the Dust by AminaGila, CourtesyTrefflin
Fandoms: How to Train Your Dragon - All Media Types, DreamWorks Dragons (Cartoon)
10 Jun 2026
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After making a deal with Viggo Grimborn and his dragon hunters, Hiccup and his dragon riders work to fulfill their end of the bargain. If they can change how the dragon hunters operate, they can protect the dragons without a war. It’s a win-win… or it would be if Viggo didn’t have his own game that he’s playing from the shadows.
Series
- Part 2 of Lines
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If You Feel Like Night Is Falling by CourtesyTrefflin, TiranaSorki
Fandoms: How to Train Your Dragon - All Media Types, How to Train Your Dragon (2025), DreamWorks Dragons (Cartoon)
10 Jun 2026
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Hiccup goes undercover with Heather to infiltrate the dragon hunters. Maybe he convinced Dagur that he’s genuinely there so they can be brothers but how long can he really keep up that act, especially when he’s trying to fool the dragon hunters at the same time? Or when Hiccup’s starting to realize that playing as Dagur’s brother isn’t entirely an act anymore?