How to Train Your Dragon Watch Order: The Complete Franchise Timeline

There are very few animated franchises that start with “awkward Viking teen befriends dragon” and somehow end with grown adults staring at the screen trying not to cry in front of their family. Yet, somehow, How to Train Your Dragon pulls it off.

All credits to DreamWorks for creating a trilogy of movies that one would argue is the studio’s best work, hands down. The franchise has everything. Breathtaking flying scenes, emotional character growth, surprisingly mature storytelling, and enough dragon species to make Pokémon trainers jealous are just the cherry on top.

But once you step outside the main trilogy, things get slightly chaotic. Suddenly, there are TV shows, holiday specials, shorts, spin-offs, and a live-action remake entering the picture like Toothless just discovered caffeine.

Thankfully, watching the franchise in the correct order is actually pretty simple. Whether you only want the essential movies or the full Berk experience, here’s the complete How to Train Your Dragon watch order.

How to Train Your Dragon Watch Order Masterlist

If you want the complete chronological experience, follow this order. We’ve simplified things for you. It includes the main movies, canon-adjacent specials, and the most relevant TV series entries. 

Too much to take in all at once? Don’t worry. This franchise is best enjoyed at your own pace. Before we dive into a sneak peek at all these entries, let’s find out which pace will suit you best.

The Best Way to Watch How to Train Your Dragon 

This franchise is nowhere near as confusing as something like Kingdom Hearts, where even the menu screen feels lore-heavy. If you’re a casual viewer, you can honestly stick to the three main movies. They tell Hiccup’s journey from awkward Viking disaster to legendary dragon chief beautifully on their own.

However, if you want more dragon action, character development, and extra adventures with Toothless and the gang, then Race to the Edge is absolutely worth watching. In fact, many fans consider it one of DreamWorks’ best animated series.

The shorts and holiday specials are more like dessert. They’re not necessary, but you’ll probably enjoy them anyway because Toothless behaves like an overgrown cat for 40 minutes straight.

Complete How to Train Your Dragon Watch Order Explained (Main Storyline)

The How to Train Your Dragon franchise may look intimidating at first glance, but it mostly follows a straightforward chronological timeline. Let’s check out what each entry has in store for you!

1. How to Train Your Dragon (2010) 

This is the movie that made everyone fall in love with dragons.

You start your journey with Hiccup, a scrawny Viking teenager who is about as suited for dragon slaying as a goldfish is for mountain climbing. Funnily enough, he befriends Toothless, a rare Night Fury dragon. 

What follows is one of DreamWorks’ best films ever made, complete with gorgeous flying scenes, emotional storytelling, and a soundtrack capable of giving people instant nostalgia damage.

2. The Early Dragon Shorts & Specials 

Before the sequels ramped things up emotionally, DreamWorks released several smaller adventures expanding Berk’s world.

A. Legend of the Boneknapper Dragon (2010)

This one is a fun little side story where Gobber tells a wildly exaggerated dragon-hunting tale that somehow gets more ridiculous every five seconds.

B. Book of Dragons (2011)

Think of this as Berk’s version of a Pokémon Pokédex episode. Hiccup catalogs different dragon species while Toothless silently judges everyone around him.

C. Gift of the Night Fury (2011)

This is a surprisingly emotional holiday special that somehow manages to make dragon migration sad. DreamWorks really had no intention of letting viewers feel emotionally stable.

3. Dragons TV Series Era 

This is where the franchise truly expands beyond the movies. 

A. Dragons: Riders of Berk (2012)

Set after the first movie, this series explores Berk adjusting to living alongside dragons instead of trying to hit them with axes every morning.

B. Dragons: Defenders of Berk (2013)

This is essentially a continuation of Riders of Berk, but with bigger threats, more dragon lore, and increasingly chaotic adventures.

C. Dragons: Race to the Edge (2015)

You’ve reached arguably the best TV entry in the franchise. This series bridges the gap between the first two movies and gives the characters far more room to grow. 

P.S. Toothless somehow becomes even more lovable, which honestly should not have been scientifically possible.

D. Dawn of the Dragon Racers (2014)

This fun prequel explains how dragon racing became Berk’s favorite sport instead of, you know, traditional Viking property destruction.

4. How to Train Your Dragon 2 (2014)

The franchise has grown considerably here. Hiccup is older, the stakes are higher, and the movie is not remotely afraid to emotionally devastate viewers when least expected.

5. How to Train Your Dragon: The Hidden World (2019)

This is the emotional conclusion to Hiccup and Toothless’ story. It’s beautiful, bittersweet, and almost guaranteed to make longtime fans stare quietly at the credits afterward.

6. How to Train Your Dragon: Homecoming (2019)

This heartfelt epilogue revisits the franchise’s themes of friendship, family, and why dragons remain cooler than almost every fictional creature ever created.

How to Train Your Dragon Watch Order for the Optional Spin-Off Series 

The entries under this one are completely disconnected from Hiccup’s storyline. So, if you were here only for Hiccup and Toothless’ dynamic (as most of us), then these can be skipped. But they can be optional for those who have kids still interested in the world.

7. Dragons Rescue Riders (2019)

This younger-skewing spin-off is aimed primarily at kids. It’s fun for families, though you’ll feel the gap in emotions because the original cast isn’t there.

8. Dragons: The Nine Realms (2021)

Set far in the future, this series imagines dragons returning to the modern world. The reception was mixed, though dragon fans will probably still find something to enjoy.

The Live-Action Era Begins for How to Train Your Dragon

This was bound to happen. It was only a matter of time. With this, DreamWorks has officially entered its “turn animated classics into live-action” phase. 

9. How to Train Your Dragon (2025) 

The live-action remake reimagines the original film while bringing Berk into a more grounded cinematic style. It’s surprisingly good (as much as live actions can be good).

10. How to Train Your Dragon 2 (2027) 

The sequel is already in development. Who asked for it? Well, DreamWorks knows people are still emotionally attached to Toothless over a decade later, so you can bet they’ll cash in on that.

Final Thoughts

The How to Train Your Dragon franchise succeeds because it grows alongside its audience. It starts as a fun fantasy adventure, and gradually becomes a surprisingly mature story about friendship, responsibility, growing up, and learning when to let go.

At the center of it all is the bond between Hiccup and Toothless, which remains one of animation’s best friendships even years later. Truth be told, any franchise capable of making millions of people (children and adults) cry over a giant flying reptile deserves respect. 

Dishari Sarkar

Writer. Dreamer. Journalist (maybe?). Anime lover (definitely). I turn curiosity into stories and everyday life into a narrative worth reading.

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