In the poem, Frost uses the word—in the final stanza—as follows:
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.
In context, the word is used both as a verb and as a noun. It is obvious that the speaker, at some future date, will reflect on the decision he made when encountering the fork in the road. He will then, he assumes, emit a sigh when he mentions the two diverging roads and the fact that he "took the one less traveled."
It is clear the "sigh" is an expression of regret. The regret would stem from the fact that the speaker will never know what difference the other road might have made. He will always wonder what the outcome would have been if he had chosen differently. He does not regret making the choice he did.
The fact that the poem is titled "The Road Not Taken" further supports this idea. The emphasis is NOT on the road which the speaker actually took, but on the other. Further emphasis for this lies in the evocative line:
Oh, I kept the first for another day!
It is obvious the speaker will forever question what would be different if he had taken the other route. This line clearly emphasizes, through the exclamation, that he will always be haunted by this thought since he assumed, at the time, that he would have an opportunity to take this alternative route at some other time. He clearly never had the opportunity to do so and will, therefore, always wonder about it, expressing a sigh when he does so.
The "difference" the speaker mentions is that he had been given a choice and decided, no matter what the outcome. There also exists, however, a conundrum in this line: How can he know what the difference is if he never saw what the other road had to offer? I suppose that question would also evoke a sigh.
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