In Cape Girardeau, Missouri, Martin Robinson is driving through the night when a truck pulls up behind him at high speed. It slams into the rear of Martin's car and slams into it repeatedly, and then disappears... only to appear ahead of Martin. He brakes to a stop and turns, and the truck chases after him. It finally sends his car off the road, backs away... and disappears.
Dean and Sam stop at a gas station en route to Pennsylvania, and Dean gets a call. He tells Sam that they're going to Missouri instead, because a friend called and said that her father died in a car crash. Dean insists that she wouldn't have called unless it was important, and tells Sam to get in. As they drive, Sam is curious and amused to learn that Dean had a steady girlfriend, Cassie Robinson, for a couple of weeks. He's also shocked to learn that Dean told Cassie the secret of what they do.
At the Cape Girardeau newspaper, Mayor Harold Todd wants Cassie and her editor, Jimmy Anderson, to bury the story about her father's death. Jimmy notes that two black men died on the same stretch of road. Mayor Todd expresses his condolences and leaves, just as dean and Sam arrive. Cassie is glad to see Dean, who introduces Sam and offers his condolences.
At the Robinson house, Cassie explains that her father claimed that a black truck was following him, and it appeared and disappeared. His car showed signs of impact, but there were only one set of tracks. The first man who died, Clayton Soames, worked at Mr. Robinson's car dealership. Cassie admits that she's skeptical about ghosts, but she can't explain what happened so she called Dean. Mrs. Robinson arrives and Dean asks to talk to her, but she says she's not up to it.
That night, the black truck drives Jimmy off the road, killing him..
The next morning, Cassie goes to the crash site and suggests that Mayor Todd close that stretch of road. He insists that he can't close the main road into town. She introduces Dean and Sam as friends of the family, and the mayor notes that there's only one set of tracks. Cassie asks if he would close the road if white men had died, and Todd angrily insists that he's no racist. When Cassie questions him on it, Todd tells her to talk to her mother if she has any doubts.
As they dress to pose as insurance investigators, Sam notes that Dean and Cassie are avoiding each other's eyes, Dean would rather not talk about it. They go into Cape Girardeau and talk to Ron Stubbins, a friend of Jimmy's, and ask him if he had any hallucinations about a truck. Ron's friend, Cyrus Dorian, recognizes their description of the truck and says there were a string of deaths of black men in the 1960s, and they disappeared in a black truck. They never found the man responsible, and Cyrus figures that the white law officers at the time weren't too interested in finding out. As they leave, Dean wonders if the truck is a ghost, reenacting previous crimes. Sam asks what is going on between Dean and Cassie, Dean admits he was stupid to let Cassie get so close, and Sam realizes that Dean loved her, and she dumped him. Dean refuses to talk about it.
That night, Cassie is working at home when Dean comes by. She says she's working on a tribute to Jimmy, who bought the paper when the Dorians sold it. Cassie wonders where Sam is, and Dean says he's busy checking the case. She notes that her mother refused to talk about her connection to Sam, and Dean wonders why she wanted to know where Sam was, and if it was easier between them with Sam there. He insists on getting down to business, and Cassie accuses him of avoiding any closeness. When he reminds her that she dumped him after he told her the truth, Cassie admits that she thought he wanted to dump at her. They snap at each other, then apologize, and then kiss. They end up in bed together
The next morning, Todd is at a construction site going over plans. He walks to his car and turns to find the black truck waiting behind him. He starts to run and the truck chases him down the road, runs him down, and then disappears.
In bed, Cassie admits that they were good at the fighting and the sex. Dean tells her that it was a big step for him to tell her the truth, and Cassie says that she thought he was nuts. She figures she was looking for a reason to walk away, but says that things can get worked out if you want them to. Dean says that he's still doing his father's work, and Cassie tells him to stop making excuses. Sam calls to tell Dean that there's been another death.
At the crash scene, Sam wonders where Dean was when he didn't make it back to the hotel, but Dean doesn't want to discuss it. They focus on the case and Sam says that every bone in Todd's body was crushed. Todd was white, and killed away from the main road, and it doesn't fit the pattern.
Dean meets with Cassie at the newspaper and tries to find a connection between Todd and the other dead men. Sam checks the courthouse records and calls to tell Dean that Todd and his wife bought an abandoned property, and the previous owner was the Dorian family. In 1963, Cyrus Dorian disappeared at the same time as the murders. Todd bulldozed the historic Dorian house when he bought the property a month ago, and the first killing was the next day.
That night, Cassie is at home alone when the lights flicker and the black truck appears outside. When she tries to close the shutters, they fly back open on their own and the black truck pulls up to the front door. Cassie calls Dean, but by the time he arrives with Sam, the truck has disappeared. Dean figures whoever was driving the truck wants Cassie frightened first. They ask Mrs. Robinson about what Martin said he saw, but she suggests he was imagining things. When Dean points out that Cassie could die, Mrs. Robinson tells them that Martin believed that Cyrus was driving the black truck. She says that Cyrus died 40 years ago, and Dean seizes on that, noting that the papers only said that Cyrus disappeared. Mrs. Robinson explains that she was with Cyrus at the time, but secretly dating Martin. When she broke it off with Cyrus and he found out about Martin, Cyrus turned hateful. That was when the black truck first appeared, but the authorities never did anything. Someone set fire to the church on the day before Mrs. Robinson and Martin were going to get married, killing the children's choir that was practicing inside. Finally, Cyrus came after Martin, who got the bat and used it to beat Cyrus to death. Martin then called Jimmy and Clayton to help him put Cyrus in the truck and then push the truck into the swamp. Todd was a deputy at the time, figured out what Martin and the others did, and did nothing.
Afterward, Dean and Sam figure that Cyrus' spirit lay in the swamp for 40 years, until Todd tore down the house and awakened it. They'll have to dredge the body out of the swamp. Cassie comes out and asks what's next, and Dean asks her to stay in the house. They go to where the truck was dumped and use the local construction equipment to bring it up. As they work, Sam figures that Dean is still in love with Cassie. They salt and burn Cyrus' remains... and the black truck appears nearby. They realize that Cyrus' spirit is infused with the truck. Dean gets in the Impala and lures Cyrus away, after telling Sam to figure out a way to burn the truck.
As Dean attempts to stay ahead of the truck, Sam goes through the maps and records, and then calls Cassie. Once he gets the information he needs, he calls Dean and pinpoints his location. Sam then tells him to take the next turn and take a left, go seven tenths of a mile, and then stop. Dean does so and Sam tells him to wait. The black truck finally charges at Dean, hits the precise spot... and slams into the spiritual remnant of gate and disappears for good. Sam confirms that his brother is okay, and explains that Dean is on the spot where the church burned down. He gambled that since evil spirits are sometimes destroyed when they step onto holy ground, the black truck would be destroyed.
The next day, Cassie says goodbye to Dean. She wonders if they might end up together, but neither one of them see much hope. They kiss and Dean hesitates for a moment, and then gets in the Impala and drives away. As they go, Sam says that he likes Cassie, and asks Dean if it's worth putting their lives on hold to do what they do. Dean just smiles and tells Sam to wake him up when it's his turn to drive.
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