He is dying--right here right now falling down dead and is wondering if it will be a bad thing like the ice falling and breaking or the apples falling and going to the cider heap. He spent a lifetime picking apples and now is his natural moment of death. This is my interpretation of the poem and what frost is conveying in this poem.
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Re: you statement: Neither of the roads is less traveled by.
Take a look at the second stanza:
Then took the other, as just as fair
And having perhaps the better claim,
Because it was grassy and wanted wear;
Meaning the other was not grassy, and more worn. I.e. more travelled by.
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Interesting fact about Frost is that he was named for Confederate General Robert E. Lee. Not what you'd expect in a "New Englander."