Known in Sindarin as Urulóki or Fire-Serpents/Fire-Drakes. The dragons were originally bred by Morgoth in the first age, though many remained in Middle Earth beyond Morgoth's time. In the 3rd age, many dragons lived in the mountains to the north of Middle Earth.
Glaurung was the first of all the dragons in Middle Earth and was known as the father of dragons. He was also known as the great worm or worm of Morgoth. Glaurung first appeared at the 4th great battle of the 1st age (Dagor Bragollach). At that time he was only half grown but he was great enough to make the elves flee before him. He was also present with many other dragons at the 5th great battle (Nirnaeth Arnoediad). Glaurung was also largely responsible for the defeat of the elves in Nargothrond, where he lived afterwards for a while.
In his later years, Glaurung's fate was closely tied with the fate of a man named Túrin, son of Húrin. Glaurung caused a great deal of grief to the family of Túrin, but Túrin finally killed him by the waters of the river Teiglin.
Smaug is probably the most well known of all the dragons in Middle Earth, since he was the chief foe in The Hobbit. He was a great golden, winged dragon. Dragons in Dungeons & Dragons and similar games are often based on Smaug since he's largely become the model for dragons in fantasy stories. Smaug first appeared in year 2770 of the 3rd age, when he drove the dwarves and humans from Erebor (The lonely mountain) and Dale. He lived there and possessed the treasure of the dwarves for many years afterward. The dwarf Thorin II had been young when he had escaped the ruin of Erebor. When he was much older, he met with Gandalf, who agreed to help the dwarves take Erebor back from the dragon. They took twelve other dwarves and the Hobbit Bilbo Baggins on a journey to Erebor. This journey ended wth the battle of 5 armies (orcs and wolves vs elves from Mirkwood, men from Esgaroth and dwarves from the Grey Mountains). Bard from Esgaroth killed Smaug with an arrow after being told that Smaug had a weak spot on his belly.
The greatest of all the winged dragons was Ancalagon the Black. At the end of the 1st Age, he lead the hosts of Morgoth against the Valar & the great eagles (lead by Thorondor - Lord of the eagles). In that battle, Anacalagon was killed by Eärendil (father of Elrond and Elros). His fall was so great that he broke the mountains of Thangorodrim.
Another dragon mentioned by name in the tales of Middle Earth was Scatha. He was killed by Frumgar, an ancestor of the kings of Rohan. Their people had been troubled by dragons but had peace for a while afterwards.
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