This song might be about Observatory Hill (a.k.a. O-Hill) in Charlottesville, Virginia, where the band formed. The railroad bridge and bike references seem to describe the area pretty well.
At an April 2007 concert at Radio City Music Hall, Matthews said about this song: "When I first wrote it, someone said, 'Is this song about you?' And I said 'no, I have no idea who it's about' And then I thought about it, and then sure enough! It was all about me! But I think this song's sort of about everybody."
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