While searching for honey, Pooh and his friends embark on an adventure to find Eeyore's missing tail and rescue Christopher Robin from an unknown monster called, The Backson. During an ordinary day in Hundred Acre Wood, Winnie the Pooh sets out to find some honey. Misinterpreting a note from Christopher Robin, Owl convinces Tigger, Rabbit, Piglet, Pooh, Kanga, Roo, and Eeyore that their young friend has been captured by a creature named "Backsoon", and they set out to save him.

As the village of Berk prepares for its winter holiday, the resident dragons all inexplicably fly away. The Viking town of Berk, now enjoying its new alliance with the dragons, is preparing for its annual winter holiday of Snoggletog. However, that spirit is threatened when all the dragons, except Toothless who needs Hiccup to help him, suddenly fly away for some reason. While Astrid ineffectually tries to salvage the occasion, Hiccup decides to build Toothless a new prosthetic to allow him to fly independently, only to have the dragon take off as well. However, as the holiday approaches, Hiccup finds himself swept up to learn the dragons' secret the hard way and to find a solution to bring them home early.

Hiccup and his friends explore and add to their primary reference about dragons. In the Great Hall, Hiccup and his fellow dragon trainers greet you as a new recruit. To get you started, the teen vikings and Gobber the Belch introduce you to their primary reference guide, The Book of Dragons. Together, you are taken on a tour of the amazing variety of dragon breeds as the young heroes add their new discoveries about handling them. Along the way, you follow the misadventures of the original author, Bork the Very, Very Unfortunate, who was fated to research his book the hard way.

Hiccup and the gang join Gobber on a quest to find a legendary boneclad Dragon. When Gobber's house burns down, the old Viking is convinced that his nemesis, the legendary Boneknapper Dragon, is responsible. Bent on revenge, Gobber resolves to hunt it down once and for all, despite the fact that no one believes the dragon exists. Regardless, Hiccup and the gang decide to accompany him for his own good. On the sea voyage, Gobber tells the story of his rivalry with the beast, which gets sillier with each episode. When the gang find themselves shipwrecked on the suspected island of the beast, they are about to learn the truth about the dragon.