Boromir's search for Imladris

[Legate of Amon Lanc]

Originally Posted by The Mouth of Sauron

A boat from the north of Wilderland travelling down Anduin would pass Lorien, not cross its border. So if either Mirkwood men or Beornings wanted to sail down to Osgiliath I don't see what was stopping them.

Undeeps.

Anyway, I guess all the places around Rauros used to be in use in the days of Gondor's glory, when its vigilance reached as far as its north border (where later there were just the folks of Wold) and also when it reached far into the East, among other things, and the Kingdom of Dale still existed, and the Northmen were there in the plains, instead of murderous Balchoth and/or instead of empty wasteland (after the wars and Great Plague).

I can see a few Woodmen trading with "the Southerners" (i.e. the Rohirrim, rather than the Gondorians by the end of Third Age), but on a rather "unofficial" and random basis, if even that. The Wilderness was wild and Dol Guldur was all too close there (as was Lórien, for that matter, which also was not a place humans would like to cross. Passing between Southern Mirkwood and Lórien would be only for the brave ones, a rather creepy experience for a common man, in my opinion).