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.

Will, a poor player who bears an uncanny resemblance to Shakespeare, auditions on stage in front of Peter, a busy producer with his nose in the trade papers, hardly noticing Will's extraordinary performance. Will, using the prop of a life-sized doll and changing costumes with magical speed, acts out brief scenes at the heart of Romeo and Juliet, Richard III, As You Like It, Hamlet, Antony and Cleopatra, Othello, Titus Andronicus, Merry Wives, the Tempest, the Winter's Tale, and other of the Bard's plays. It's an infinite variety show, and finally Peter's attention is on Will. What will the producer say when Will finishes?