The first major road trip I took by myself was in the summer of 1999. I went to Seattle first, where I spend quite some time before really starting the trip. On the day I left, I drove I-90. It crosses the top of Idaho. It's a really beautiful drive through the pine tree covered mountains. I hit that as the sun was setting. I had been listening to Jimi Hendrix - The Ultimate Experience. At the end of the album is Jimi's Star Spangled Banner from Woodstock. The sights and the sounds made the most awesome amalgam of existence for my drive.
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