What is the answer to the question Thoreau asked in Chapter 2 about the poem of a shepherd?
"There was a shepherd that did live,
And held his thoughts as high
As there the mounts whereon his flocks
Did hourly feed him by."
the question is "What should we think of the shepherd's life if his flocks always wandered to higher pastures than his thoughts?"
When Henry David Thoreau went into the woods and lived at Walden Pond, he went into nature in order "to live deliberately" and to see if he
"could not learn what it [nature] had to teach, and not, when I came to die discover that I had not lived."
While in these woods, Thoreau experiences the majesty and infiniteness of the heavens and ponds that reflect these heavens. And, he learns what it is to live freely where the
winds which passed over my dwelling were such as sweep over the ridges of mountains, bearing the broken strains, or celestial parts only, of celestial music.
In contrast to Thoreau who feels no confinement or restraint and feels that his little house
was at an equal remoteness from the life which [he] had left behind dwindled and twinkling with as fine a ray to my nearest neighbor, and to be seen by my nearest neighbor only in moonless nights by him
the shepherd must remain close to his sheep and his thoughts can rise only as high as his sheep mount:
and held his thoughts as high
As were the mounts whereon his flocks
Did hourly feed him by.
Dependent upon some other force to elevate him, the shepherd is much like the sheep himself as he is led by another force. Thoreau, as a Transcendalist found this idea anathema, for he believed in the importance of individualism and the integrity of the self. For both Thoreau and his contemporary Ralph Waldo Emerson, self-expression was paramount. Man should, according to Thoreau, "march to the beat of a different drummer," not be like the shepherd, who has lost his humanity and individuality as he merely follows his sheep even in thought.
To me, what Thoreau is saying is that we should pity or maybe even scorn such a shepherd. That shepherd would be living such a mundane life that Thoreau would think it wasn't really much of a life.
What Thoreau is talking about in the part of the book right before this poem is how his mind would wander as he hung out in the wild areas around his home. He says that he lived in whatever part of history he wanted and that his home was nearer to various stars and constellations than it was to his neighbors. What he is really saying is that his physical surroundings were less important than where his mind went.
Thoreau is arguing that it is important to live in your mind and to have an active life in your mind. If your thoughts can wander (metaphorically) no higher than your sheep, you are not living a fully human life (because you are not using your human faculties of reason and imagination).