Bixby Canyon Bridge

I think this song is about Ben Gibbard's "last bender" before he stopped drinking. In an article with the Guardian, he said, "I gave up drinking three years ago after a trip where I tried to "recreate" the novel Big Sur. I could see how On the Road was all about not having a care in the world, allowing the long nights and excesses to define you in the positive the way most people do when they're young. But Big Sur was the proverbial end of the road, and it showed me how that kind of lifestyle can end in alcoholism. There's footage of Kerouac at the end of his life when he's a horrible drunk and really embittered; I found myself in literally the same place, staying in a cabin he'd stayed in and knowing how it ended because I had read the book. Big Sur is the most beautiful place in the US, but when you're in a disturbed emotional state the vastness of it was upsetting — it felt like evil spirits were lurking there. I've been back to that cabin a number of times and once again it looks beautiful, and I wonder how I could ever have felt so unsettled."

I think he's talking about following Kerouac's footsteps ("All the way from San Francisco / As I chased the end of your road / 'cause I've still got miles to go") before realizing that he doesn't want to end up in the same place that Kerouac ended up, and at the low point of his trip to Big Sur, he's starting to see that he's going to ruin himself if he keeps drinking, but futhermore, if he keeps living the reckless "college kid" life all the way through his adulthood. ("And I want to know my fate / if I keep up this way.")

The line about how it's "hard to want to stay awake" when everyone else is asleep is drawing on the concept of being the guy staying up late drinking while your settled-down peers are at home in bed with their spouses, and applying that image to those comparative lifestyles in general. When you admire someone like Kerouac to the point of emulating them, you're bound to emulate their mistakes - and as he [Ben] reaches that point, he realizes that this is the person he wants to emulate at all, though he's also "no closer to any kind of truth", implying that he no longer knows what kind of person he is or wants to become. I think that's a killer closing line.