Hiccup is more brains than brawn, a smart, funny and savvy kid desperately looking to prove himself to his father, Stoick the Vast. While the villagers, who tower over Hiccup in height and girth, battle the dragons destroying their crops, Hiccup is relegated to the blacksmithing workshop. Once alone, Hiccup takes his newly invented weapon outside and attempts to take down the most feared dragon of them all, a night fury. Things don't entirely go to plan, and his father admonishes him publicly.
Hiccup sets out to find the night fury dragon he believes he hit the night before with his new invention. After locating the dragon, Hiccup empathises with the creature and realises he can't kill it, setting it free instead. Hiccup returns home to tell his chieftain father Stoick the Vast the truth. However, his dad has decided it's time for Hiccup to begin dragon training and become a Viking. At training, Hiccup tries to blend in with the other recruits.
Hiccup finds the night fury dragon stuck in a ravine, missing a caudal fin and unable to fly. That night, the recruits are told to study each dragon, but they see no value in reading and leave Hiccup alone. Hiccup discovers a consistent theme, "kill on sight". Meanwhile, the Vikings hunt for the dragon nest. During training, Astrid tells Hiccup to choose sides, but Hiccup realises he can't. Hiccup bonds with the dragon he has named Toothless.
Realising Toothless is in danger if he can't fly, Hiccup uses his creative intelligence to forge his new friend a prosthetic caudal fin. When testing the device, Hiccup distracts the dragon with a basket of fish and a smoked eel, learning the dragon is scared of eel. Hiccup uses this new knowledge during training, much to the amazement of everyone. Hiccup continues to learn more about dragon behaviour through he interactions with Toothless.
After perfecting the prosthetic caudal fin and a successful flying lesson with Toothless, Hiccup realises that everything the village knows about the dragons is wrong. When Stoick the Vast returns home, he tries to talk to Hiccup about his new dragon-fighting skills. Receiving such praise for the first time from his father, Hiccup has conflicting emotions and he is unable to tell him the truth about his new abilities.
At the tournament, Hiccup is crowned the winner and told he must kill a dragon during an exam the next day. Unwilling to hurt the creature, Hiccup packs a bag and runs away. Astrid finds and confronts Hiccup and Toothless, but sees that the village's relationship to dragons could be very different if they just learnt to understand each other.
During the final exam, Hiccup attempts to show the village that dragons are misunderstood by calming the dragon. Stoick the Vast becomes enraged and calls off the fight, startling the dragon and inciting chaos. Toothless hears that Hiccup is in trouble and sets out to rescue him. After the villages capture Toothless, Hiccup argues with his father about the treatment of dragons. Disregarding Hiccup's words, Stoick the Vast shackles Toothless and uses him to find the dragon's nest.
Astrid reminds Hiccup that his "differences" have led to his greatest achievements, reminding him to be brave and trust himself. The young recruits join forces to help Hiccup to rescue Toothless. At the nest, Stoick the Vast realises he's been a fool. Together, Astrid, Snotlout, Ruffnut, Tuffnut, Fishlegs, Toothless and the other dragons work together to save everyone from a colossal red death dragon.
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