Hi Matt,
Treebeard claims the Entwives went in search of lush nicely ordered pastures, orchards and the like far back in the past. He then seems to allude that some/all of their new lands were scorched in the Dark Days and thats when they lost touch.
Apparently the countryside of the Shire is the sort of environment that they like, and near the start of LOTR, Sam actually says that his cousin saw a "giant, a treeman, up away beyond the Water,".
The Old Forest also has Entish/Huorn connections, with that cranky Old Man Willow and all...
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'…Avallónë, the haven of the Eldar upon Eressëa, easternmost of the Undying Lands, and thence at times the Firstborn still would come sailing to Númenor in oarless boats, as white birds flying from the sunset…'
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