It is possible. One does get the impression that perhaps Bombadil wandered over a wider area in the past.
However, I doubt he played a great role in history. It would seem to go against the theme of observation, which is one of the reasons why Tolkien put him in there in the first place.
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...finding a path that cannot be found, walking a road that cannot be seen, climbing a ladder that was never placed, or reading a paragraph that has no...
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