16 books in series

How to Train Your Dragon

How to Train Your Dragon is a 16-book series with 16 primary works first released in 1999 with contributions by Cressida Cowell.

Hiccup
How to Train Your Dragon
How to Train Your Viking, by Toothless the Dragon
How to Be a Pirate: The Heroic Misadventures of Hiccup the Viking
How to Speak Dragonese
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The Incomplete Book of Dragons

How to Cheat a Dragon's Curse
How to Twist a Dragon's Tale
A Hero's Guide to Deadly Dragons
How To Ride A Dragon's Storm
How to Break a Dragon's Heart
How to Steal a Dragon's Sword
How to Seize a Dragon's Jewel
How to Betray a Dragon's Hero
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How to Fight a Dragon’s Fury

The Day of the Dreader