If this song depicts travelogue, it takes place over a relatively small slice of a very large country. The speaker-- we assume it is Simon himself, as his travelling companion is Kathy, presumably the same one as in "Kathy's Song"-- started (as far as we know) in Saginaw, MI. It took him "four days to hitch-hike," from there to... where it is they are together boarding "a Greyhound [bus] in Pittsburgh." The only other location we are given is "The New Jersey Turnpike." Obviously, they are travelling east.
If they are only seeing one part of the country, then, do they mean when say they are "look[ing] for America"?
If they were looking for the "real America," as in the small towns of the Heartland... well, they were closer when they were in Michigan to begin with. They went past Philadelphia, too, so they are not looking for America's birthplace or a sense of its history. They are not looking for the tourist's America, the one comprised of a checklist of natural wonders and national landmarks; they do not go to Mt. Rushmore, the Grand Canyon, or Niagara Falls.
But one need not have a map or a GPS to know that Simon is from New York, and that's where "America" is for him. And, if you travel from Pittsburgh east along the Pennsylvania Turnpike, you hit the New Jersey Turnpike, which takes you north to New York City.
But he's not there, yet. The song ends with him still on the road. In the first verse, it's "we... walked off to look for America." Then Simon tells Kathy: "I've come to look for America." Then, almost to their probable destination, Kathy has nodded off, but Simon tells her anyway, "I'm lost." He has "look[ed]" and "look[ed]" and is still "lost". Then Simon projects his sense of being lost to the rest of the travelers on his highway: "They've all come to look for America!"
No wonder he can't find it. No one else can, either. All they can do is travel the highways, looking.
Along the way, we learn about their relationship from the details provided. They throw in together willingly; they smoke and read magazines. They like to pass the time by improvising intrigues about their fellow passengers: That fellow is just too self-consciously stuffy-looking, with his "gabardine suit" and his "bow tie"-- he must be a "spy"!
And, just as Simon notices the Moon, we must notice how he evokes the roundness of it with the assonance of the long O. He sees it as it "rOse Over an Open" meadow [capitals mine]. He doesn't say, yet he shows, that this is a full Moon.
Simon doesn't realize it, but he has found America... in that he hasn't. America, after all, is less a place than a state of being. And that is a state of yearning, of being pulled forward toward an endlessly receding destination. "I'm empty, and aching, and I don't know why."
The whole trip is about moving. He didn't live in Saginaw, he hitch-hiked "from" there. He didn't visit Pittsburgh, he "boarded a Greyhound" there. He does not mention his destination, but he also makes no mention of relocating there or staying there for any length of time.
This is the unlike his feeling in "Kathy's Song" and "Homeward Bound," in which he yearns to be somewhere specific he is not. Here, he knows he is not home, yet he can't seem to imagine where that could be, either.
Then where his is home, such as it is? He tells us that in the first verse: "I've got some real estate here in my bag." His home is the road. George Carlin explained, in his famous "Place for My Stuff" routine, that a house is "just a pile of stuff with a lid on it." Well, Simon's "place for his stuff" is in his bag. All he needs is some junk food, cigarettes, and a magazine... and he's set.
As he approaches New York, Simon should feel excited. After all, as the song goes, if he can make it there, he can make it anywhere. Instead, he is filled, as it were, with emptiness. This isn't going to be any better than anyplace else, he just knows.
But this is the "place" that is America. America is less a noun than a verb. You can't "look for America"-- America is a state of looking, searching, seeking. A Greyhound bus never ends up anywhere; it just takes you to the next town.
One last note on the song's structure; it seems loose, as the rhymes are non-existent, yet it adheres to a rather strict waltz cadence.
A beautiful song, and a favorite of S&G fans, if not one of their most recognizable hits on the level of "Mrs. Robinson," "Bridge," or "Sound of Silence."
Next Song: Overs