The two diverging roads in Frost's poem are undoubtedly metaphorical and represent choices he had to make about career and lifestyle. This is confirmed by Frost himself in a letter he wrote to a young girl many years ago, which I am quoting below:
No wonder you were a little puzzled over the end of my Road Not Taken. It was my rather private jest at the expense of those who might think I would yet live to be sorry for the way I had taken in life. I suppose I was gently teasing them. I'm not really a very regretful person, but for your solicitousness on my behalf I'm
your friend always
[Finger, L. L.: "Frost's 'The Road Not Taken': a 1925 Letter come to Light", American Literature v.50]
This was posted in eNotes under topic of The Road Not Taken by tiff72 on March 10, 2009. You can look it up in eNotes if you wish.
Frost believed that anything written should be dramatic or it was worthless. He made "The Road Not Taken" dramatic by describing a conflict. Conflict is the heart and soul of drama. The traveler (Frost himself) comes to a fork in a road in a yellow wood (indicating the season and his time of life) and is forced to make a choice without knowing where either road will lead. The road he chose "was grassy and wanted wear." This is a metaphorical way of saying that, unlike the majority of men, he chose to live a simple, frugal life in order to be able to devote his time and thought to his creative writiing. In this way he resembles Henry David Thoreau, author of Walden, another New Englander who decided to forgo the pursuit of material success in order to devote his life to philosophy, the love of nature, and creative writing.
It is easy to see in Frost's poetry what sort of actual choice he made. His most famous poems, such as "Stopping By Woods on a Snowy Evening," reveal his choice of a life of simplicity and communing with nature. The road not taken might have led to one of the major cities instead of a New England farm. He might have become rich and lived in luxury. He might have even become a banker or a stock broker or a captain of industry. He intentionally relinquished those things, which is why he is telling about it with a sigh. The sigh, incidentally, is indicated by the break in the lines
Two roads diverged in a wood, and I --
I took the one less traveled by,
But as he says in a letter written many years ago to a girl about your own age, "I'm not really a very regretful person." The road of life he chose led him great success as a poet. He is generally considered the best-loved American poet. His popularity is partly due to his emphasis on drama in his poetry.
There is something a little puzzling about the first two lines of the last stanza.
I shall be telling this with a sigh
Somewhere ages and ages hence:
"Ages and ages" suggests centuries. Did Frost believe in personal immortality? Or did he expect this particular poem to be read by many future generations? In that respect, he was correct. It looks as if he will continue to be read for a long time to come.