Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,

I have always taken this poem to be a metaphor for individualism and non-conformity...taking the least traveled road. Of course, this theme is deeply imbedded in New England's spirit and psyche going back to the Transcendentalists, its greatest champion being Ralph Waldo Emerson (if you haven't read his essay Self-Reliance, you should). But now I look at the italicized portion of the above stanza and wonder if, from a more mature perspective, the more rugged path is less relevant than the fact that he chose the right path for him at the time. The more traveled path would have be a mistake for him at that particular juncture, but perhaps it would have been the correct choice for someone else, as long as it was their truest path.