How to Train Your Dragon Movies: Animated Films
The original animated trilogy of How to Train Your Dragon presents Hiccup and Toothless's complete story arc as a cohesive narrative spanning from adolescence to adulthood. This watch order focuses exclusively on DreamWorks Animation's three interconnected films, which tell a linear story of friendship, growth, and the evolution of an entire society.
Each film builds on the previous entry, following the characters as they mature and face increasingly complex challenges. The trilogy concludes Hiccup's journey from village misfit to wise chief, providing satisfying closure to major character arcs while maintaining excellent narrative continuity.
There is 1 other watch order available – see the link up above.

How to Train Your Dragon
A young Viking named Hiccup discovers that dragons aren't the monsters his village believes them to be when he befriends an injured dragon he names Toothless. Their unlikely friendship challenges everything Hiccup has been taught about being a warrior and forces him to choose between tradition and compassion.

How to Train Your Dragon 2
Five years after uniting dragons and Vikings, Hiccup and Toothless discover a secret world of wild dragons and face a new threat from a power-hungry warrior seeking to conquer Berk.

How to Train Your Dragon: The Hidden World
Hiccup works to create a peaceful dragon utopia while Toothless discovers a mate, but mounting dangers force both dragon and rider to make difficult choices to protect their world.
Other Film Series
Jumanji
A magical adventure series about a supernatural board game that brings its jungle dangers into the real world.
Night at the Museum
A family adventure trilogy following night security guard Larry Daley as he discovers that museum exhibits come to life after dark, leading to magical adventures with historical figures and ancient artifacts.
Percy Jackson
A fantasy adventure duology following a teenage demigod as he discovers his divine heritage and navigates the modern world of Greek mythology.
The Chronicles of Narnia
A fantasy trilogy based on C.S. Lewis's popular novels, following the Pevensie children's adventures in the magical world of Narnia.
The Wizard of Oz
A collection of reimaginings and retellings of L. Frank Baum's classic tale, spanning from the iconic 1939 musical to modern interpretations.
Witch Mountain
A Disney science fiction series about children with extraordinary psychic abilities seeking refuge and their true origins.