It came to pass that on one his frequent explorations around Rivendell, he came upon the High Pass in the Misty Mountains. As he searched this pass a terrible rain storm began, forcing him to take shelter in a small cave. That night with the storm shaking the very walls of the cave, Legolin was suprised by a large number of goblins that inhabited the mountains.
He was bound and taken to their leader in the Goblin caves. Alone and without weapons, the young elf still conducted himself in a proud manner, not giving signs of weakness to the goblins that raged around him.
The goblins began to prepare a fire, for cooking their new dinner, but Legolin undid his bonds and lept towards the leader, grasping him by the throat. The goblins began to shriek and rage as he threw their leader into the fire and rushed into the darkness.
After wandering for sometime in the gloom, he was aware of a small creature lurking in the depths. Legolin questioned this thing and found he was Gollum. Legolin asked about the way out, and Gollum proposed a game, a game of riddles. If he won he would get the way out, if he lost, he would die. Without choice Legolin accepted. Gollum had played this game many times, yet here was no dim-witted orc, but a wise elven ranger.
Legolin won the game of riddles, but Gollum wouldn't let him go, until he snatched a ring from Gollum's hand, the Ring of Power. Gollum quickly led him to the exit of the cave and Legolin gave back the ring, nver dreaming how important it was.
Upon exiting the cave, Legolin was set upon by a group of wargs and orcs. Weaponless, he ran to a large tree, and climbed it. Seeing the orcs bring fire, he prepared for a final leap to take as many orcs as possible with him before he died, but the jump never came. Gwaihir, the lord of the Eagles, was near and saved the elf from death that day, begining a bond of friendship and respect that continued forever between Legolin and the lord of the Eagles.