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Summary
This journal is old, older than Dean thought, and it starts with a list. From what Dean can tell, it catalogues a bunch of landmarks. Roadside attractions. Silly, stupid ones like the World’s Largest Ball of Twine—of which Sam notes there are actually three, in three different states—and Herkimer, Colorado’s Largest Beetle. Dean remembers seeing at least one of those balls of twine, back when he was a little kid, and it’s probably the one from Cawker City, Kansas, because Sam’s got that one crossed out.
There’s other things too. Museums, galleries, national parks. Those seem more Sam’s style, but he doesn’t appear to discriminate much. Many places are checked off; some Dean can remember going to and others he can’t.
Clutching that notebook to his chest, he thinks he knows what he’s going to do next. Lisa—if she even wants him—she can wait. He’ll finish up some maintenance on the car. He’ll pack a bag. Then, he’s going to drive.
(Post-S5) After the events of Swan Song, Sam stays dead. While unpacking Sam’s old duffel bag, Dean finds a journal with a bucket list inside, and instead of going back to Lisa, he decides to finish it. Eventually, Castiel comes along for the ride.