The narrator debates for some time before making his choice. The narrator states that he "looked down one as far as I could" as he tried to make his choice. He sees that both roads were freshly covered with leaves and finds both of them "fair" in appearance. In the end, the basis of his choice of which road to take is that the road he takes "wanted wear."
In looking back on his choice, the narrator is somewhat sad, resigned to the facts of life that he assumes mean he won't get an opportunity in the future to travel the road he did not choose. "I shall be telling this with a sigh" seems to indicate some degree of regret. However, he doesn't indicate any remorse about the route he did follow; indeed, he acknowledges the impact of the decision upon his life when he says, "I took the one less traveled by, and that has made all the difference."