Located on a remote island, the Viking village of Berk is frequently attacked by dragons who steal cattle, damage property and endanger lives. Hiccup, the clumsy fifteen-year-old son of village chief Stoick the Vast, is deemed too thin and weak to fight the dragons. Instead, he makes mechanical devices as part of his apprenticeship with Gobber, the village blacksmith, although Hiccup's inventions often backfire. During an attack, Hiccup uses a bola launcher to defeat a Night Fury, a dangerous and rare dragon little is known about. No one believes him, so he searches for the fallen dragon alone. He finds the dragon in the forest, tangled in its web, but cannot bring himself to kill it and frees it instead.
Stoick assembles a fleet to find the Dragon's Nest to end it once and for all. Before leaving, he enters Hiccup in a dragon fighting lesson being taught by Gobber along with fellow teens Fishlegs, Snotlout, twins Ruffnut and Tuffnut, and Astrid, a tough Viking girl Hiccup has a crush on. After failing the training, Hiccup returns to the forest to find the Night Fury still there, trapped in a creek and unable to fly due to Hiccup's bolas accidentally ripping off half of its tail fin. Hiccup offers the Dragonfish and slowly befriends it, naming it "Toothless" after its retractable teeth. Feeling guilty about crippling Toothless, Hiccup designs a harness and prosthetic fin that allows the dragon to fly, but only when Hiccup rides and controls the prosthetic.
Hiccup learns the behavior of dragons while working with Toothless, and is able to subtly and nonviolently overpower captive dragons during training, earning him the admiration of his peers but making Astrid increasingly jealous and suspicious. Meanwhile, Stoick's fleet returns home unsuccessfully, though Stoick is pleased with Hiccup's unexpected success at kite training. Hiccup is considered the winner of his training class and has to slay a dragon for his final exam. He tries to escape with Toothless, but Astrid ambushes him in the forest and discovers the dragon. Hiccup takes Astrid on a sunset flight to demonstrate that Toothless is friendly. Toothless takes the couple unexpectedly to the Dragon's Nest, where they discover a gigantic dragon called the Red Death. The smaller dragons constantly feed it live food to avoid being eaten themselves. The two realize that the dragons were forced to attack Berk in order to survive. Astrid wants to inform the village of her discovery, but Hiccup advises against protecting Toothless.
Returning to the village the next day, Hiccup confronts a captive Monster Nightmare dragon during his final exam. However, instead of killing him, he tries to subdue him to prove that dragons can be peaceful. When Stoick accidentally angers the dragon into attacking, Toothless escapes the bay to protect Hiccup, but is captured by the Vikings in the process. Hiccup accidentally reveals to Stoick that Toothless knows the location of the dragon's nest. Though Hiccup warned his father that confronting the Red Death would kill him, Stoick disowns his son and sets out for the nest with Toothless, chained to the lead ship, as his guide. After the Vikings leave, Hiccup is devastated, but Astrid tricks him into realizing that he spared Toothless out of compassion and empathy, not weakness. Hiccup then regains his confidence to pursue Toothless. He shows Astrid and the other teenagers how to befriend the training kites.
The Viking raiders locate and open the Dragon's Nest, awakening the Red Death, who soon overwhelms the Vikings. Hiccup, Astrid, and their friends arrive by plane, ride Berk's captured training kites, provide cover fire, and distract the Red Death while Hiccup frees Toothless. Hiccup almost drowns in the process, but Stoick saves them both and is reconciled with his son. Toothless and Hiccup destroy the Red Death by piercing its wing membranes and then causing the beast to dive from where it cannot recover. Toothless protects Hiccup from the ensuing explosion, but Hiccup loses his left leg. Hiccup wakes up on Berk to find that Gobber made him a prosthetic and he is now admired by his village, including Astrid kissing him. Berk begins a new era where humans and dragons live in harmony.
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