This question is not as straightforward as it appears. The reason for that is because Chris McCandless and Wayne Westerberg interact with each other on more than two occasions. So I can't know exactly which "again" that the question is referring to. I am going to assume that the "again" is referring to the second time that Westerberg and McCandless see each other.
Wayne Westerberg owned a grain elevator in Carthage, South Dakota, but every summer he operated a custom combine. He would follow the harvest north from Texas all the way to the Canadian border.
In the early fall of 1990, he was wrapping up the season and preparing to return to Carthage. On September 10, in northern Montana, Westerberg picked up a hitchhiker. That hitchhiker was none other than Chris "Supertramp" McCandless.
The two of them drove together into a small town, had a beer together, and chatted for a bit. McCandless told Westerberg that he was heading for a place several hundred miles down the highway. Westerberg told him that he could take him part of the way. When it was time to drop McCandless off, it was raining hard, and Westerberg felt guilty. Westerberg offered to shelter McCandless for the night, and McCandless agreed. McCandless ended up staying with Westerberg for three days. At the end of the three days, McCandless said that he was moving on. Westerberg told McCandless that he owned a grain elevator in South Dakota and that he would give him work if he ever showed up in Carthage.
To Westerberg's surprise, McCandless showed up a couple of weeks later. That, I believe, is the "when" that your question is referring to.
“Was only a couple of weeks that went by before Alex showed up in town,” Westerberg remembers. He gave McCandless employment at the grain elevator and rented him a cheap room in one of the two houses he owned.
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