This poem is often misunderstood. People often think he has taken the less traveled road, implying that he took a road that was “off the beaten path.” This would convey that the speaker purposefully chose to take an unconventional path.
But, he describes two similar roads. He is face with a choice.
Two roads diverged in a yellow wood,
And sorry I could not travel both (1-2)
So far we know that he has come to a fork, diverging into two roads. Then he makes his choice. He can only guess that this path is less traveled.
Then took the other, 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
And both that morning equally lay (6-11)
They look similar (“just as fair”). Then he supposes he made the better choice because the path looks less worn. Then he realizes both paths probably had been worn about the same: equal paths.
In the last stanza, he says he will speak of this choice later in life. He will say that he took the road less traveled by, but he will say it with a sigh. The sigh is the key. He can only assume he made the right choice, just as he can only assume the path he chose was less traveled. At the place he made his choice both paths looked the same. Both were covered with leaves (line 16). This is symbolic of choices in life when we are not sure what to do. Which is less conformist, more genuine, etc.? We just have to choose. Any choice will make all the difference. He will always wonder about the road he didn’t take.