how to train your dragon in order

The "How to Train Your Dragon" series can be enjoyed in several orders depending on whether one wants to read the books or watch the movies and shows. Here are the recommended orders:

Book Series Order by Cressida Cowell:

1. How to Train Your Dragon (2004)
2. How to Be a Pirate (2005)
3. How to Speak Dragonese (2006)
4. How to Cheat a Dragon's Curse (2007)
5. How to Twist a Dragon's Tale (2008)
6. A Hero’s Guide to Deadly Dragons (2009)
7. How to Ride a Dragon’s Storm (2010)
8. How to Break a Dragon’s Heart (2011)
9. How to Steal a Dragon’s Sword (2012)
10. How to Seize a Dragon’s Jewel (2013)
11. How to Betray a Dragon’s Hero (2013)
12. How to Fight a Dragon’s Fury (2015)

Movie & TV Watching Order (Chronological & Release):

1. How to Train Your Dragon (2010 movie)
2. DreamWorks Dragons: Legend of the Boneknapper Dragon (short)
3. How to Train Your Dragon: The Book of Dragons
4. Dragons: Gift of the Night Fury
5. Dragons: Riders of Berk (TV series)
6. Dragons: Defenders of Berk (TV series)
7. Dragons: Race to the Edge (TV series)
8. How to Train Your Dragon 2 (2014 movie)
9. Dragons: Dawn of the Dragon Racers
10. How to Train Your Dragon: The Hidden World (2019 movie)
11. How to Train Your Dragon: Homecoming (special)
12. Dragons: The Nine Realms (TV series) [optional]

If focusing on the essentials, just watching the three main movies in order (2010, 2014, 2019) provides the main story arc. The TV series and shorts add depth and side stories. This order provides the best flow for understanding the plot and character development of Hiccup and Toothless, whether reading or watching.