How to Train Your Dragon School Books in Order

The How to Train Your Dragon School series returns to the world of Hiccup Horrendous Haddock the Third, but in a format designed for younger, developing readers. These are shorter, heavily illustrated chapter books that sit between early readers and the longer How to Train Your Dragon novels, keeping the same mix of slapstick danger and heart but with simpler sentences and plenty of pictures.

In this spin off, Hiccup, his dragon Toothless, and the loyal wind dragon Windwalker are attending the Viking and Dragon Training School on the Isle of Berk. On paper it sounds glorious, a place where young warriors and dragons learn to fly, fight, and become heroes. In reality, Hiccup and his friends are stuck firmly at the bottom of every class, always in trouble, and constantly one mishap away from disaster.

The first book, Doom of the Darkwing, begins with what is meant to be a quiet lesson in the “Art of Battle”. Instead, thanks to a chain of small mistakes, Hiccup and his classmates end up adrift on stormy seas in a damaged ship with a terrifying sea dragon closing in. The story unfolds in short, punchy chapters, switching between action scenes, arguments between Vikings and dragons, and Hiccup’s attempts to think his way out of a situation that bravery alone cannot fix.

Because these stories are set earlier in Hiccup’s training, readers get to spend more time with the school side of Berk, the teachers, fellow trainees, and the daily routines of feeding stables full of dragons who would rather set everything on fire. The books lean into classroom comedy, with disastrous homework, mix ups over equipment, and the endless struggle to remember instructions when you are dangling from a dragon’s tail.

Cressida Cowell illustrates the series herself, packing the margins with sketches of dragons, maps, labels, and small asides that feel like scribbles in the margins of Hiccup’s own school notebooks. The design uses lots of white space, big fonts, and frequent illustrations, which lowers the intimidation factor for children who are moving up from picture books but still like a visual nudge on every page.

Although the scale of the adventures is a little smaller than in the main novels, the themes are similar. Hiccup is still the boy who would rather be kind and clever than cruel and loud. He is still learning to listen to dragons, stand up to bullies, and prove that there is more than one way to be a hero. For keen How to Train Your Dragon fans, the series offers extra time with favourite characters and a chance to see them at school. For new readers, it can be an easier way into Berk before tackling the longer books.