On a cool, wintery Christmas Eve, Jack accompanies North while he delivers presents to the children of the world. (Post ROTG.)

Hiccup wishes that Toothless and the other dragons were there to spend Snoggletog with him and the others. Astrid comes and comforts him, and the two then receive a surprise visit from none other than their old dragon companions. (Post HTTYD: THW.)

It's that time of year again. The year where North and Bunny argue if Christmas is better than Easter. The year where Tooth has to remind everyone to brush well after eating too many Christmas cookies. The year where Sandy consumes a not so healthy amount of eggnog. And the year Jack realizes how imperfectly perfect his new family is. (Post ROTG.)

Jack has met the Guardians before. Not when he was an immortal and not when he became a Guardian but while he was still a regular human boy living in colonial Burgess. (Pre ROTG.)

Hiccup wakes up with a phantom pain, but due to his extreme stubbornness, he goes out flying with his friends. But when the pain becomes too unbearable for him to handle, Hiccup soon realizes with the help from Astrid that it's okay to ask for help. (Post HTTYD. One-shot.)

The Man in the Moon decides that it's time to bring an end to the Dark Ages and he choses four very special people to help with his mission. But how can a Pooka, an ex-Cossack, a former Star Captain, and a Sister of Flight end the Nightmare King's reign and bring wonder, hope, and light into the world and children once again? (Pre ROTG.)

The youths of the Academy head out to investigate an island that is said to have strange things happening on it. Then, the next morning, they wake up to find that their personalities have been swapped. After some digging, the Riders find out that a rare dragon is the cause of the switch, and set out to save it from the Outcasts' clutches before they use it for harm. (Post ROB.)

Hiccup finally gains the courage to ask Astrid out on a date and of course something just has to go wrong. When Hiccup and Astrid find themselves captured by Dragon Hunters, they're going to have to rely on each other to make it out alive. Maybe this little outing with Astrid was just a date with disaster all along. (RTTE.)