In How To Train Your Dragon 2
In the film, Hiccup is pressured by Stoick to become chief, but Hiccup runs away with Toothless from Berk. While flying Hiccup and Toothless are taken by Valka and her Stormcutter Cloudjumper to her secret ice cave that is home to hundred of dragons that Valka rescued from Drago Bludvist and Eret's traps. Hiccup soon realizes that he and Toothless are in the center of a battle to protect the peace between both men and dragons.
Abilities and Talents
Being the main character of the franchise, Hiccup has many varied and useful talents.
Dragon Training and Riding: Though he only discovers this ability during the first film, Hiccup has grown to become the best dragon trainer on the Island. His dragon Toothless is the rarest and best dragon in the academy. Hiccup openly claims to be the best dragon rider in the episode Thawfest. He and Toothless clearly have the strongest bond in the series. Because of his talents he has been made head of the Berk Dragon Academy. In the franchise, Hiccup is always the one looked to when Dragon related problems or needs come up. He trains a wild Monstrous Nightmare in seconds in Defiant One. This is noticeably faster than even Astrid who had to train a similar type of Dragon and does manage to do so but takes longer. He's also able to keep an enraged Whispering Death from running over him by simply putting his hand forward. Still, some Dragon challenges (including said Whispering Death) are greater than his ability, but he can always rely on Toothless and the other teens to have his back.
Drawing: Even before Hiccup began to train Dragons, he practiced drawing. He is practically never without his journal and a large charcoal pencil. His sketches are usually quick and slightly messy, but compared to most other Vikings he is quite good. He uses this talent often. He sketches Toothless upon his second encounter with him. He uses his notebook to copy the map to the Isle of Night (unfortunately). He uses his artist talent to aid him in making plans and inventions. His room is littered with drawings of Toothless.
Before Hiccup lost his leg he was shown to have a talent in snowboarding while performing snowboarding tricks in the Racing For The Gold adverts.
Inventing: Hiccup learned a great deal about crafting from Gobber. His many years of apprenticeship have certainly paid off. He has created many ingenious devices throughout the franchise. He uses the forge well (despite his small size), and he's excellent at working leather. His devices were originally weapon like, and the mangler cannon he designed allowed him to take down a Night Fury. After training Toothless he shifted in his desires and started working on a new tail for Toothless. This tail has been modified many times and is a work of sheer genius. He even created an auto tail using complex gear systems. Besides that Hiccup has managed to design a plethora of other objects, from winches to telescopes. It's most likely that he invented his own flight suit and his Fire Sword, Inferno.
Intelligence: This talent is really at the heart of all Hiccup's other abilities. His intelligence is proven many times throughout the film and the series. He's almost always the one to come up with the solutions to the problems that the Riders face. He's shown to be very cunning, resourceful and perceptive and possesses a great aptitude for strategy and tactics. He's also fairly knowledgeable. Unlike Fishlegs who only spews out facts, Hiccup is able to use them for practical use and he does it very well. He was able to solve all the riddles on Hamish's treasure map even when under pressure and the feat is especially notable because it was said that only a most brilliant mind could solve those clues.
Fighting: Due to Hiccup's initial size, he's not much of a fighter. In fact, most weapons are too heavy for him and struggles to lift them. He is a very skilled sword fighter in the books though. Hiccup usually fights along side Toothless. Their style is more about defense. The only time Hiccup and Toothless attacked first was against Alvin in We Are Family Part II. Other than that, it is easy for others to overtake Hiccup. InThe Night and the Fury, Hiccup faces Dagur with his new shield. In Cast Out Part II, Hiccup fought Outcasts and Berserkers without a problem using his shield. Preview art of the second movie shows Hiccup with a flaming sword called Inferno, so it is possible that he learns how to use one at some point between Defenders of Berk and How to Train Your Dragon 2. It was also shown in the trailer, Hiccup jumping off a Monstrous Nightmare (Hookfang) and releasing his wing-suit to glide into Drago's army and him dodging a trap during his gliding so this might prove he'll do actual fighting in the second film.
Roar Call: He can make a roar noise that sounds similar to Toothless's roar. A way for Toothless to find Hiccup.
Accuracy: Like Toothless, Hiccup has amazing aim, like when he was able to shoot down Toothless in the first film and hit a Deadly Nadder in the chest using his shield while flying in mid-air during Appetite for Destruction.
Endurance: While it may seem hard to believe at first, Hiccup always manages to bounce back from a severe injury. For example, in When Lightning Strikes, he was struck by a massive and direct bolt of lightning, and still managed to wake up just a day after. Also, in the end of How to Train Your Dragon, he was knocked off of Toothless by the Red Death's massive club-tail, and (with the help of Toothless, of course) managed to wake up about a week, (or longer), later.