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Our speaker has come to a fork in a path in the woods. It's fall, and the leaves are turning colors. He's unsure which way to go, and wishes he could go both ways. He looks down one path as far as he can see, but then he decides to take the other. He thinks the path he decides to take is not quite as worn as the other one, but really, the paths are about the same, and the fallen leaves on both look pretty fresh.
The speaker reflects on how he plans to take the road that he didn't take another day, but suspects that he probably won't ever come back. Instead, far off in the future, he'll be talking about how his decision was final and life changing.