‘How to Train Your Dragon’: Celebrating 20 Years of Adventures

We’re celebrating the 20th anniversary of ‘How to Train Your Dragon.’ Explore the long life of the book series turned blockbusters here!

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Not many people know that the DreamWorks Animation hit franchise How to Train Your Dragon is loosely based on an extensive book series by British children’s author Cressida Cowell. In the book that started it all, Hiccup Horrendous Haddock III, the smallish Viking with a longish name, tries to pass the important initiation test of his Viking clan by catching and training a dragon. Can Hiccup do it without being torn limb from limb? And, when a new terror threatens to devour every Viking on the Isle of Berk, can he save the tribe and become a hero?

To celebrate 20th anniversary of this masterful children’s series, let’s explore the adventures of Hiccup, Toothless, and their zany friends in How to Train Your Dragon.

1. How to Train Your Dragon

illustration of Hiccup and Toothless in How to Train Your Dragon

Hiccup and his friends begin the Isle of Berk’s rite of passage to catch, tame, and train their own dragon. Out of all the dragons available to him, Hiccup chooses the runt of the pack, naming him Toothless.

During their final examination, the boys’ dragons begin a fight, leading to the gang’s exile from Berk. The group discovers a Sea Dragon called Green Death, who’s on a mission to kill all Vikings. While the elders squirm to fight their imminent doom, Hiccup and Toothless recklessly attack Green Death, hoping to save the day and their home.

2. How to Be a Pirate

illustration of Camicazi in How to Train Your Dragon

Hiccup’s father, Stoic the Vast, is chief of the Hairy Hooligan tribe, which means Hiccup is the Heir to the throne, but that’s not the future he asked for. When a huge, six-and-a-half-foot floating coffin with the words “BEWARE! DO NOT OPEN THIS COFFIN” arrives, can you guess what happens next?

The Quest to discover the treasure of Hiccup’s ancestors begins and Hiccup needs to find it before Alvin the Treacherous gets his hands on it. But, when a dragon called the Monstrous Strangulator is thrown into the mix, things begin to get seriously scary.

3. How to Speak Dragonese

illustration of Dragon Vocabulary in How to Train Your Dragon

When Hiccup’s dragon Toothless is captured by Romans, only Hiccup and his friend Fishlegs can rescue him. But things get worse when they get lost at sea and the Romans steal Hiccup’s precious book, How to Speak Dragonese, and Hiccup and Fishlegs are taken off to the Fortress of Sinister! There, they bump into an old enemy, Alvin the Treacherous, and a new friend, Camicazi. They must escape by banding together, but not everyone can be trusted.

4. How to Cheat a Dragon’s Curse

illustration of different characters in How to Train Your Dragon

Hiccup’s best friend, Fishlegs, thinks he has a nasty cold, but Old Wrinkly has diagnosed him with vorpentitis, caused by the sting of a Venomous Vorpent, planted by Alvin the Treacherous. The only antidote is the Vegetable-that-No-one-Dares-Name: the potato.

But the only way for Hiccup to find the cure is to face Norbert the Nutjob and the terrifying Sea Dragon, Doomfang. But what they come to discover is that Fishlegs isn’t the one infected, and that potato is their only hope.

5. How to Twist a Dragon’s Tale

illustration of Exterminators in How to Train Your Dragon

While on a herding exercise the children are attacked by evil fire dragons called Exterminators. Hiccup and Gobber are saved by the world famous hero, Humungously Hotshot, hired by Stoic to become Hiccup’s personal bodyguard.

One night Hiccup wakes to Hotshot debating whether or not to kill Hiccup in his sleep. Hotshop begins to tell the story of a woman he once loved and a friend he calls Terrific Al. Hiccup soon finds out that the woman in the story is his own mother, and Terrific Al is his arch enemy, Alvin the Treacherous, now seeking his revenge.

6. A Hero’s Guide to Deadly Dragons

illustration of A Viking's Guide to Deadly Dragons in How to Train Your Dragon

Hiccup, Camicazi, and Fishlegs go to the Island of Forget Me to visit the Meathead Public Library in search of another copy of How to Train Your Dragon. With the help of Stormfly, Camicazi’s dragon, they find a second edition as well as a book written by Hiccup Horrendous Haddock II: A Hero’s Guide To Deadly Dragons. Nevertheless, the gang have disturbed and stolen from the Hairy Scary Librarian, who’s willing to kill to get her books back.

7. How to Ride a Dragon’s Storm

illustration of Doomfangs in How to Train Your Dragon

Madguts the Murderous invites the Bog-burglars and the Hairy Hooligans to join the Murderous Tribe for an Intertribal Friendly Swimming race. The winner being the last person back, may have a single request granted by the three Chiefs.

During the race Hiccup, Fishlegs, and Camicazi are pulled onto a boat packed with slaves called Northern Wanderers. They all plan to escape when the boat is attacked by a Leviathorgan, a Sea Dragon they must fight off to survive, but not before Hiccup can be left with a detrimental mark. With all this taking up a lot of time, however, there’s even a chance that Hiccup might still “win” the race.

8. How to Break a Dragon’s Heart

illustration of the Evil Witch in How to Train Your Dragon

Camicazi has been shipwrecked and the Hooligans are on a mission to find her. They end up shipwrecked on a haunted beach belonging to wicked pirates called Uglithugs. While on the beach, they find a mysterious object, and they discover it is a throne belonging to Hooligans.

UG, the leader of the Uglithugs, tells Hiccup that a Hooligan has been sending love letters to his daughter, Tantrum O’Ugerly, and explains that if the person is of royal blood, the person can ask for Tantrum’s hand in marriage if they finish an Impossible Task. If not, the person will be killed.

Hiccup realizes that Fishlegs is the one who sent the letters, and spares his friend’s life by telling UG that he himself wrote the letters. UG then tells him the Impossible Task: by 5:00 the next day, he must give them a barrel of mead made from the honey made by bees on the Island of Berserk.

9. How to Steal a Dragon’s Sword

illustration of sword-fighting manual in How to Train Your Dragon

Hiccup and other young warriors are brought to Flashburn’s School of Swordfighting, where they will have three weeks to train in sword fighting for New Year’s Day.

When they arrive, the only person there is the wicked witch Excellinor. She tells the tribes that the sword fighting competition must be used to find the next king of the Wilderwest, who, according to prophecy has a dragon with no teeth, an arrow from a land that does not exist, Grimbeard’s second-best sword, a ticking-thing, a rectangular shield, a throne, a crown, and the Dragon Jewel.

Of course, it’s Hiccup who, through his past adventures, has collected all but three: the throne, the crown, and the dragon jewel. Soon something will be discovered that will lead to Hiccup’s exile from his own tribe.

10. How to Seize a Dragon’s Jewel

illustration of the map to the dragon jewel in How to Train Your Dragon

Picking up from the last book, Hiccup is exiled and traveling to a slave jail run by none other than Alvin the Treacherous, who has won UG’s competition and become King, declaring war on the dragons. But what can Hiccup do now, all alone and in exile, hunted by both humans and dragons? Can he find the Dragon Jewel, mankind’s last and only hope and become the Hero once again? What he does discover is the fate of his best friend Fishlegs: to be sucked into a hole in the ground.

11. How to Betray a Dragon’s Hero

illustration of Scary Dragon in How to Train Your Dragon

Hiccup and his friends hear a human calling for help, then, a deadly silence. They find Snotlout, with Wolf-fangs in the river and thousands of Dragon Rebellion dragons sleeping on the riverbank. Hiccup persuades the rest of the group to save him, accidentally waking up Snotlout’s Hogfly and the nearby Rebellion dragons. They all flee to their secret hideout, hiding as Furious and the dragons search for them.

Alvin’s Spydragons kidnap Camicazi, so Snotlout brings them on a rescue mission to save her. When escaping from the Alvinsmen, Snotlout is shot down and killed. Hiccup’s lament forgives him for his bullying and praises his later work as a strong young Viking.

12. How to Fight a Dragon’s Fury

illustration of Toothless in How to Train Your Dragon

Hiccup wakes up on the beach at Hero’s End with amnesia, sustained when he hit his head at the end of the previous book. As the Wodensfang tries to explain who Hiccup is, they are attacked by Sharkworms and the Vampire Spydragon.

After defeating the dragons, Hiccup takes a boat that has washed up on the beach and sails towards Tomorrow. There, Hiccup makes his way to Grimbeard the Ghastly’s castle just as Alvin is about to be crowned king by the Druid Guardian. Hiccup regains his memory and gives a speech convincing the Druid Guardian to crown him king instead.

While Hiccup and Furious come to a peace, Furious is attacked by Alvin and the Witch leading to an all-out Vikings vs. Dragons battle. Furious saves Hiccup’s life by sacrificing his own and ends the war once and for all. Hiccup can finally build a new kingdom of hope and peace on Tomorrow.

The Author

photo of Cressida Cowell, author of How to Train Your Dragon

Just like the Hiccup, Cressida Cowell spent most of her childhood summers on a small, uninhabited island off the west coast of Scotland. It was there that she started to explore her love for writing and drawing. The isolation and tranquility of the island no doubt influenced the creation of the fantastical island of Berk and gave way to the masterful series of Viking Dragon Riders. The series spans 12 full novels, following Hiccup and Toothless as they grow up together and face wondrous adventures and treacherous villains.

illustration of the map of Berk in How to Train Your Dragon

When she started writing the series 20 years ago, Cowell could never have imagined the multitude of spin-off novels, movies, and TV shows she would inspire:


  • How to Train Your Dragon (2010)
  • How to Train Your Dragon 2 (2014)
  • How to Train Your Dragon: The Hidden World (2019)

Short Films

  • Legend of the Boneknapper Dragon (2010)
  • Book of Dragons (2010)
  • Gift of the Night Fury (2011)
  • Dawn of the Dragon Racers (2014)
  • How to Train Your Dragon: Homecoming (2019)

TV Shows

  • DreamWorks Dragons (2012-2018)
    • Riders of Berk
    • Defenders of Berk
    • Race to the Edge
  • DreamWorks Dragons: Rescue Riders
    • Heroes of the Sky
  • DreamWorks Dragons: The Nine Realms
How to Train Your Dragon logo

Beyond the How to Train Your Dragon series, Cowell has authored multiple children’s standalone books and the following series:

Even if the movies are vastly different from the books, Cowell’s Viking/Dragon universe has been impactful for multiple generations. She has created a legacy that will continue to hold a place in our hearts for years to come.

For more books like How to Train Your Dragon, click here. Want more on Cressida Cowell? click here!