When Toothless lost his left tail fin after a dragon attack on Berk, Hiccup made a new tail for him. Quickly learning that he needed to control the fin himself, Hiccup also made a saddle with a little stirrup connected to the tail, so he could ride Toothless for long periods, allowing him to control the tail fin all the while.
In the Riders of Berk episode, "Viking for Hire", after peace was made with the dragons, Hiccup and Gobber started to make saddles for the Dragon Riders and their dragons when they complained of feeling sore after riding their dragons for hours. However, Gobber added certain features to their saddles such as horns, maces, catapults and even flamethrowers, which Hiccup and the other riders soon found to be counterproductive. So, aside from Hiccup who had a saddle from the beginning, they went without saddles until "In Dragons We Trust", when it's uncertain who finally made appropriate saddles for each rider and their dragon. They're seen in every episode of the series ever since.
In another part of the Viking Empire, a blacksmith from Huttsgalor named Hannahr observed that some visiting Dragon Riders could use a saddle for the benefit of both rider and dragon. She crafted a saddle to fit the Swiftwing, Winger. This was also a gesture of thanks for helping to get her forge re-lit in "The Nest". At some point in the next six months, she also made one to fit the Fastfin, Summer. A saddle functioning as a carry harness for the Rockspitter, Burple, appears in "Home Alone".
Saddle designs are extremely variable, depending on the species of dragon it will be used on and secondary purpose such as battle, extended travel, or racing.
According to School of Dragons, components of a basic saddle include fleece, leather, leather straps, and metal nuts and bolts, as mentioned in the player Quest "Saddle Up Vikings". Players can purchase a variety of saddles for their dragons ranging from Wild and Novice Saddles, to the more bulky Defenders saddle. At this time, not all dragon species in the game have saddles available. Quality varies also, some are unique to each species, while others are "cookie cutter" style, one version conformed to different species. Some saddles also give the player boosts in racing such as speed or turning.
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