LotR -- Book 4 - Chapter 01 - The Taming of Sméagol

[Kuruharan]

I was rereading this today a passage stuck in my mind in a way it never had before.

Frodo looked straight into Gollum's eyes which flinched and twisted away. "You know that, or you guess well enough, Smeagol," he said quietly and sternly. "We are going to Mordor, of course. And you know the way there, I believe."

"Ach! sss!" said Gollum. covering his ears with his hands, as if such frankness and the open speaking of the names, hurt him. "We guessed, yes we guessed," he whispered; "and we didn't want them to go, did we?"

This is an interesting exchange for a number of reasons. Gollum was obviously in possession of information that Sauron lacked. However, it makes one wonder how long Gollum had suspected that Frodo was on his way to Mordor. Sauron never guessed that the Ring was on its way to anyplace other than Minas Tirith. Did Gollum also believe that was where Frodo was headed or did he think from the time that he picked up the Fellowship's trail that they were going to Mordor? That also brings up the issue of what Gollum thought Frodo was doing…