Frost does an exceptional job of building up to--and one might even say disguising-- the core philosophical question of this poem. In the first two stanzas, he paints a picture with skill such that any of the Imagists could have no complaints about his form. It is only in the third stanza that I realized Frost's storyteller is not just recounting his physical travels, but building a metaphor for his emotional state. Suddenly, we are greeted by a connection to a human with: "The heart is still aching to seek, / But the feet question 'whither?'" Until this point, there was only plant-life, landscape, and the idea of a journeyman--in contrast with his form.
Beyond the form and expression of his poem (which I could comment much further on), Frost technically asking the reader a question, but I feel his meaning is closer to that of a quiet lamentation. He is commenting on something I think all of us have experienced at some point or another: the difficulty to move on. We can know intellectually that it's time, there may be signs all around us--like dead leaves at our feet such as in the poem--and yet the heart may not be ready to let go. It is this aspect of human nature that Frost is seeking to express.
The message here is universal to human beings. From one person to the next, I'm sure we can find someone with a deep attachment to something that goes beyond their ability to reason. I think this also has its connection to the realm of ethical philosophy, where the ability to reason clearly and at least have an understanding of one's attachments is fundamental. This unwillingness of the heart to move on is natural. And I honestly believe in many cases it can be enriching to the person feeling this way (provided they can process these feelings in a healthy way). At the same time, I think we must learn to temper our attachments with reason.
Thanks for reading!
"Reluctance" by Robert Frost @ Poetry Foundation:
http://www.poetryfoundation.org/poem/238118