After Mildew poisons all the dragons on the island, he is forced to help Hiccup, Stoick, and Gobber find and capture the ferocious Scauldron in order to get the antidote.

Caught in a waterspout, Toothless' prosthetic tail is damaged, rendering him unable to fly and thus leaving him, Hiccup and Snotlout stranded on Outcast Island. The three must work together to repair the damage, overcome the rivalry between Hiccup and Snotlout and return home to Berk before they are captured by Alvin and the Outcasts.

When Hiccup discovers Trader Johann's ship was shipwrecked in a rumored haunted bog with a gift made for him by his mother, he will stop at nothing to retrieve it.

Mildew has betrayed the Vikings of Berk and allowed Alvin the Treacherous to kidnap Hiccup and Toothless. Astrid and Stoick must rescue them from Outcast Island along with help from a new friend.

Hiccup and Toothless return from a mission to find Berk mysteriously empty. They discover that the village has been overrun by Speed Stingers, a venomous non-flying dragon that has trekked across the frozen sea to Berk.

The mysterious theft of metal objects all over Berk reveals the presence of marauding Smokebreaths. Hiccup and Toothless soon discover that these dragons are the work of Dagur, in a plot to render Berk defenseless.