A similar question was asked not too long ago (see the link below).
In my response to that question, I challenged the popular reading of the poem. I wrote:
I see the Frost poem "The Road Not Taken" in a very different way than the two previous posters. My reading is supported by at least two reputable sources, which are identified at the end of this posting. Both sources state that the poem can be read one way on the surface (readers often don’t move past this superficial reading, unfortunately) and a very different, more compelling and more complex way if the reader pays close attention to the language of the poem.
In 1961, Frost commented that “The Road Not Taken” is “a tricky poem, very tricky.” The trickiness may lie in the speaker's contradictions in characterizing the diverging roads. At first, the two roads seem very different, but upon closer analysis, these differences all but vanish. The second stanza opens by asserting that the one road is “just as fair” as the other and ends with the statement that “the passing there / Had worn them really about the same.” Stanza three includes a similarly contradictory statement. The two roads do not appear to be different at all; they “equally lay / In leaves no step had trodden black.”
What are we to make of these contradictions? A number of critics argue that the poem actually mocks (with good humor) our tendency to look back on our past (just like the speaker, who jumps forward in time in the final stanza of the poem) and to assign all sorts of significance to our past actions. In reality, we know that there are multiple ways to get to any one place; it often really doesn’t matter all that much which particular road we take.
The central issue in the poem is one of choice. If the first stanza is the exposition of the poem, it outlines the fundamental dilemma that faces many in consciousness. The speaker of the poem is faced with two choices and can only select one. There is a level of agony within this idea of incompatible courses of action. The remainder of the poem examines the criteria behind why the speaker selected the chosen path. This is very similar towards any particular choice that individuals have to make. The essence behind any choice is why one chose what was chosen and whether or not they would do it again, if the opportunity presented itself. This is confirmed in the closing lines in terms of the choice made has made "all the difference." In the final analysis, I think that the poem outlines the critical elements behind choice and the calculus that goes into any exercise of freedom within incompatible courses of the good.