You'll Never Leave Harlan Alive
performed by Brad Paisley

The Crowder and the Bennett clans go to war over control of Harlan, a move that leaves dead and dying on both sides. The episode begins with Boyd making a deal with Doyle's ambitious deputy in order to exchange information of the sheriff's (by extension the Bennetts') movements. Winona tells Raylan that she is pregnant. Loretta goes missing, and Raylan goes after her, further antagonizing Winona and forcing her to seek help from Art. Art says he can't help Raylan as he's off-duty. Raylan suspects correctly that Loretta ran away on purpose and is trying to avenge her father. Boyd and Mags call a meeting to settle the tension. Mags sets up an ambush on Johnny Crowders home, and Ava Crowder's home. Johnny responds by blowing up his house, killing the two assassins. Also revealing that Boyd was aware of the "surprise' ambush by the Bennetts, the attack on Ava's house leaves all the Bennett hired guns dead, with the exception of Dickie. Dickie manages to shoot Ava in the chest before escaping, and her fate is left unknown. While searching for Loretta, Raylan is hung by his leg from a tree as Dickie hits him with a baseball bat to make up for the limp Raylan gave him. Raylan is in mortal danger until Boyd shows up, presumably acting on a tip of Dickie's whereabouts from Doyle's deputy. Raylan is about to let Boyd kill Dickie until Dickie persuades Raylan that he needs him alive to save Loretta, who is on her way to Mags. Raylan and Dickie drive to the Bennet home, where Loretta confronts Mags directly about what really happened to her father. When Loretta shoots Mags in the leg, the Bennet forces shoot Raylan in the stomach while Dickie jumps in the car for safety. Just as Doyle is about to shoot Raylan, he gets shot in the head by the U.S. Marshals, who Art has brought to save Raylan. Dickie is once again taken into police custody, though his charges are unknown. Raylan then confronts Loretta, who gets Mags to confess to murdering her father. Raylan persuades Loretta not to kill Mags, and she eventually relents, being taken into custody. The episode ends with Raylan and Mags drinking her homemade moonshine (Apple Pie), with Mags poisoning herself the same way she killed Loretta's father. The feud is settled with a handshake as she dies.

In the first season finale, Harlan is turned into a battlefield when the tense situation between Raylan, Arlo, Boyd and Bo Crowder finally comes to a head. When Bo sadistically kills all of his son's followers, Boyd looks to Raylan for help. Arlo's plan to betray Raylan is found out, and he is shot by Raylan. Ava is kidnapped by Bo and Johnny Crowder, after which, Bo shoots Johnny for suspected collusion with Boyd. Boyd and Raylan go after Bo to rescue Ava. At the standoff, Bo is unexpectedly killed, in an ambush, by Miami gun runners who are after Raylan. Raylan and Boyd manage to save Ava and kill three of them, but one of them escapes. Raylan is forced to let Boyd (who calls Raylan his "only friend") chase after Bo's surviving killer.