Astrid: So what do you want to do now?
Hiccup: Probably something stupid.
Astrid: Okay, but you have already done that.
Hiccup: Then something crazy!
Astrid: That's more like it!
If you watch closely at the beginning of the movie, when the DreamWorks logo appears on screen, you can see Toothless flying around in the stars behind the moon. See more...
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How to Train Your Dragon (2010) - 16 mistakes
Continuity: When Hiccup first finds Toothless, there is a dramatic shot where the camera pans over Toothless, and his wing briefly obscures his eye, which is open after the wing passes. But look at the tip of the wing. During the shot there is a stretch of rope wrapped around it. In the next shot, the rope is much higher up the wing and not wrapped around it anymore.
Plot hole: During one of the test drives, the hook that Hiccup uses to fasten himself to Toothless gets bent, so he takes Toothless to the blacksmith to cut the line. There are two ways he could have easily avoided this: He could just unhook the saddle, take that to the blacksmith and cut himself loose, or he could just untie the leather strap. What he does here is needlessly risky and just there for his awkward conversation with Astrid.
Plot hole: Just before the village elder chooses Hiccup as the winner of Dragon Training, Hiccup achieves victory by subduing a Gronckle and making it fall asleep, in such a way it cutely kicks its leg in satisfaction. It is shown that Hiccup's father, Stoick, is watching the entire thing. So how did he not notice that Hiccup used a trick like that to beat the Gronckle and become aware that something was off at that point?
Continuity: After Toothless and Hiccup defeat the giant dragon, Stoick finds Toothless on the ground and believes his son to have perished in the battle. As he is kneeling down and beginning to morn, the rest of the Vikings begin to emerge from the smoke behind him. They are a good distance away from Stoick. But in the very next shot, they suddenly jump much closer to him.
Continuity: In the scene where Hiccup trials his first tail fin, he gives Toothless a basket of fish. This falls off his face before he takes flight. However, the basket is never seen again; you don't see it under either wing from behind, and when he takes flight the little bit of ground he was standing on is gone.
Plot hole: When Astrid gets on Toothless for the first time, Toothless takes off uncontrollably and tries to scare her. Hiccup seems to have no control over him at this time. How is that so if with the new tail fin, Toothless cannot fly without Hiccup's precise control of the tail fin? That whole sequence would have fallen apart. This mistake was even admitted to on the DVD Commentary.
Continuity: When Stoick has the other Vikings blow a hole in the mountain with catapults, he then has a fire ball fired down the new cave and it shows hundreds of dragons all over the walls and ceiling. When Stoick yells and charges forward, the dragons scatter and rush out the hole in a panic, but far fewer dragons are shown escaping the hole.
Continuity: Near the beginning, as Hiccup is chased by the monstrous nightmare, the pole he hides behind gets blasted. If you look at it, the base is made of steel plates, but after Stoick beats the dragon and the camera switches back, the metal is gone and it's just wood. There is no way it melted off and burned the wood that far and that fast.