Of course, this is a matter of opinion and speculation. The speaker tells us at the end of the poem that taking the less traveled road has made all the difference. This implies that it mattered what choice the traveler made, but tellingly, he does not specify what the difference was.

As the speaker looks both ways at the fork in the road, he notes that the roads are not much different. In fact, he says, neither road has been travelled on that morning:

And both that morning equally lay

In leaves no step had trodden black.

I think the purpose of the poem is to make the reader consider the impact of decisions made during life. My interpretation of what will happen as a result of the poet's decision to take the road less traveled isn't as important as that every reader finds his/her own meaning.

In answer to your question, however, I think the traveler would have been disappointed if the choice had been to take the more traveled path. In reading the poem, I think the traveler enjoys time to discover and experience on his/her own, without lots of company along the way. Therefore, I don't think the traveler would have enjoyed the trip as much if it had not been taken on "the road less traveled."