Originally posted by Legate of Amon Lanc:
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Last but not least, I believe that it was not much pleasant idea to carry the Ring through the Gladden Fields, even though it would be on the western shore this time. Also who knows how the area was passable (seems that it was quite swampy).
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There is one other reason to avoid the Gladden Fields altogether. It was common knowledge where Isildur lost the Ring, and it was known that Gollum found the Ring in that vicinity. They even knew that Sauron knew as much. It's logical to think that the orcs that engineered Gollum's escape from Mirkwood were sent with Sauron's knowledge, in hopes that Gollum would lead him to the Ring eventually. Since Gollum was from that area originally, Sauron was likely paying special attention to that area. Sauron knew that "Shire" was far to the west, but there was still some chance that the Ring remained in the area where it was last known to be. Whether his spies were seen or not, he was no doubt having the area searched or at least watched. This would be a good reason to avoid the Gladden Pass and the High Pass in favor of something further south.