The Istari and Arnor's fall

[Inziladun]

Originally Posted by urbanhiker

Still, I find it remarkable that Tolkien apparently chose not to textually elaborate on their early deeds and doings, particularly those of Gandalf and Saruman, when he elaborates on almost everyone and everything else! What kinds of fascinating little journeys and struggles and experiences did they have? I've never read anything but the trilogy, the Hobbit and the Silmarillion so maybe a loremaster on this site will provide us with illumination.

The essay The Istari from Unfinished Tales is one of the best sources of information about them. Regarding Gandalf specifically, it says:

But [Gandalf] is seldom mentioned in any annals or records during the second millennium of the Third Age. Probably he wandered long (in various guises), engaged not in deeds and events but in exploring the hearts of Elves and Men who had been and might still be expected to be opposed to Sauron.

That is consistent with the Tale of Years, which states that it was only in the year 2063 (in the third millennium) of the Third Age that Gandalf made a visit to Dol Guldur to investigate whether Sauron was there. It simply appears that Sauron was the main focus of the Istari, and of the side matters that did not directly involve the resistance to him, they did not concern themselves. As an example, it was only the potential of Smaug the Dragon being used by Sauron to cause mayhem and destruction in the North that moved Gandalf to help with the recovery of Erebor.