As for entwives north of the Shire, that seems rather unlikely:
In "Letters #144:
Quote:
I think that in fact the Entwives had disappeared for good, being destroyed with their gardens in the war of the Last Alliance...when Sauron pursued a scorched earth policy and burned their land against the advance of the Allies down the Anduin. They survived only in the 'agriculture' transmitted to men (and Hobbits)... Some, of course, may have fled east, or even have become enslaved: tyrants even in such tales must have an economic and agricultural background to their soldiers and metal-workers. If any survived so, they would indeed be far estranged from the Ents, and any rapprochement would be difficult-unless experience of industrialized and militarized agriculture had made them a little more anarchic. I hope so. I don't know.
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Also, it's interesting that the estrangement of the ents and the entwives
seems an instance of "blame" accruing to both sides, rather reminiscent
of the long-term hostility of elves and dwarves, similarly with "blame"
being possible to attribute to either side.