Perhaps the High Pass is called "High" relative to the other option. I wonder if it may have been at a higher atltitude, and thus, maybe, even more perilous to cross than the Redhorn in the depths of winter.
We also no little (I think) about the land immediately east and south of the High Pass and west of the Anduin. Perhaps it is especially rugged, and it's certainly easy to imagine the marshy areas around the Gladden aren't a king's highway. Perhaps the region is also thick with Sauronic forces amassing for their eventual attacks on Lorien.
The land between Mirkwood and Anduin does seem passable, based mainly on Isildur's path after the Last Alliance, but obviously not without passing very close to Dol Guldur.
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From without the World, though all things may be forethought in music or foreshown in vision from afar, to those who enter verily into Eä each in its time shall be met at unawares as something new and unforetold.
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