During a sleepover with Roger, Steve shows off his rebuilt Macintosh computer and vintage games, including The Oregon Trail, in which Roger is appalled to see that virtually every ending results in death. Family photo day fails to cheer him up, and Stan's horseplay in the car results in a fiery crash that makes it appear that Roger has perished. A year later, Steve still honors Roger's memory but the rest of the family has developed quirks.
Meanwhile, Roger had faked his death and has hit the road as a renegade, although a rapid series of motorcycle accidents leads Steve to suspect that Roger still lives and figures out that he is riding the Oregon Trail. Roger stops in a diner, but balks at taking on an outlaw biker gang. In a restroom, he spies a notice for a renegade and follows the lead, discovering that it was really Steve who used it to draw him in. Roger admits that he can't deal with losing the Smiths as he did an earlier family that traversed the Oregon Trail but agrees to go back home with Steve.
However, he uses the opportunity to trap the family in Steve's Macintosh so that they can live forever. They try to get a message to Klaus, but get caught so they decide to play The Oregon Trail so they can put their plea for help on a printout in Klaus' carryout. To Roger's horror, they proceed to die over and over again, until they manage to complete the game. They awaken to find themselves free from the computer, not because of Klaus, but because their numerous deaths desensitized Roger to their eventual passing.
Meanwhile, Klaus opens a carryout in Roger's attic, but suspects everyone of trying to rob him. When he shoots a health inspector, he wounds himself as well to make it appear as if there was a shootout. While he is injured, his store is robbed by a Boar's Head meat deliveryman.