What's the meaning behind the poem "Where the Sidewalk Ends"?

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Where the Sidewalk Ends,” by Shel Silverstein, is at once a melancholic and hopeful poem. Silverstein creates a contrast between, on the one hand, a melancholic place, characterized by “dark street[s]," “asphalt flowers," and smoke that "blows black," and on the other hand, a place “where the sidewalk ends,” where “the grass grows soft and white" and “the sun burns crimson bright.” These two places are symbolic of adulthood and childhood, respectively, as indicated by the fact that the children are the only ones who “know / The place where the sidewalk ends.”

The place that symbolizes adulthood seems to be full of darkness, whether it be in the form of the black smoke, the “dark street[s],” or “the pits where the asphalt flowers grow.” This darkness connotes ignorance, emptiness, and, perhaps, immorality. The darkness of this place is also emphasized in contrast to the brightness of the other place, where the grass is white and the sun “burns...bright.” In contrast to the darkness, the brightness here connotes clarity, innocence, and purity.

In summary, the speaker seems to be suggesting that childhood is a time of clarity, innocence, and purity, whereas adulthood is a time characterized by the loss or absence of those virtues. We have clarity in childhood because life seems so simple; in adulthood, life seems to become infinitely more complicated. In childhood, we are innocent and pure; in adulthood, we have succumbed to the temptations of sin.

The speaker in the poem represents childhood and adulthood metaphorically as real places, because in this way he can be hopeful of returning to the simplicity and innocence of his childhood, leaving the complications and sinfulness of his adulthood behind. The meaning of the poem is that we should all endeavor to make this same journey—from a life of sin to one of innocence, and from a life of complications to one of clarity.

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"Where the Sidewalk Ends" is a poem about getting to a place outside of the city.  Stanza two narrates details about the negative parts of city life.  

Let us leave this place where the smoke blows black
And the dark street winds and bends.

The sidewalk is a symbolic roadway to getting out of the city.  When a person has reached the end of the sidewalk, he has reached the outside of the city.  What's outside of the city?  Great happiness, beautiful scenery, and a peaceful aura.  

And there the grass grows soft and white,
And there the sun burns crimson bright,
And there the moon-bird rests from his flight
To cool in the peppermint wind.

Now, whether or not Silverstein is writing about a real location outside of cities or an imaginary one is up for some debate.  Personally, I think it's an imaginary location.  If you have a copy of the book, the cover has a picture of where the sidewalk ends.  It's basically the edge of the known world.  I've linked a picture below.  I think Silverstein is reminding and encouraging readers to return to the joys of having a child-like imagination.  It's a form of escapism, and Silverstein wants to remind his readers how great those imaginary adventures were to those great places that had nothing to do with city streets, traffic, deadlines, etc.  I think the meaning of the poem is its encouragement to readers to remember to have some child-like fun and imagination.  

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