There are two misunderstandings that occur when reading this poem.
First, middle school students have an odd trouble even picturing this poem. They don’t get it. For many teachers, or adults, this poem seems easy, but middle school students blow through it and we let them because the lesson seems obvious. They don’t get it. Slow down. Put them in front of that fork, on the path, and let them slowly choose. Have them describe each path, and think about the benefits and drawbacks of each. Keep it concrete, and about the paths themselves.
Second, most readers, adult or otherwise, disparage the road not taken. More traveled, people assume that Frost is saying that it is a bad road. He does not. Indeed, he goes out of his way to describe that road as of equal worth; it’s just not for him. It seems, that if he had time, he would take both.
This is an important point. We all like to think we are rebels and are taking the road not taken, but in truth our path is pretty worn. Still, that is not a bad thing. Frost is saying, I think, that we need to take the path that is best for us. Taking a path filled with brambles just to be different is not a better trip.
So, after visualizing the actual roads you can move to having students see it as a metaphor. For this, leap to the end. What, you should ask, made all of the difference? Why? This can lead many directions, from peer presure, to clothing choices and even their life dreams. It is also a good prompt for a memoir or personal essay. What made the difference in their life, and which path was it?
A note: I have avoided this and similar poems because they are often used, but also not in the public domain. Still, it is a cultural touchstone and students should be exposed to it or they’ll get their interpretations on the streets from other kids. We all know where that leads to. Frost poems “Snowy Day” and “Mending Wall” are longer and require more effort, but work great with kids, too.
The Road Not Taken
Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;
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,
And both that morning equally lay
In leaves no step had trodden black.
Oh, I marked the first for another day!
Yet knowing how way leads on to way
I doubted if I should ever come back.
I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I,
I took the one less traveled by,
And that has made all the difference.