Dawn of the Dragon Riders!
Released in 2014, this 26.38 min long short is about the origins of a new sport Hiccup and his friends had made just after the events of the first movie. This short movie is fun to watch and adds even more lore to this series! As described on the back of the DVD case, "Hiccup, Toothless, and their fearless friends are flying higher than ever in an all-new adenture-- and Berk will never be the same! When a hunt for lost sheep turns into a fierce, fun filled competition, the villagers will defy tradition to prove who is the fastest in the island's first Dragon Racing Championship". Personally, I loved it but it wouldn't be the first short I'd pick out of the bunch