In 1863 in Greenville, Ohio, when Union troops stop at the Dixon house to conscript young Drew Dixon into the army, Drew’s mother protests that they have already lost their elder son in battle and that it is not fair to take another son from her. Unsympathetic to her plight, the officer in charge orders that the house be searched for Drew, but when the soldiers are unable to locate him, they leave. Drew then comes out of hiding, after which his parents give him his brother’s gold watch and $100, which he hides in his boot, and instruct him to go to Virginia City, Nevada, which is outside Union jurisdiction, and wait there until the war is over. Upon arriving in St. Joseph, Missouri, where he plans to join a wagon train headed West, Drew observes a long line of travelers waiting to book passage. As Drew walks to the end of the line, he finds himself in front of the army recruiting station and nervously rambles on. Drew’s furtive behavior is noticed by Jake Rumsey, a fast-talking young man about his age, who stops Drew and warns him that there is a six-month waiting list for the wagon train. Drew, who has been advised by his God-fearing mother to seek out a “good Methodist family” upon reaching town, asks Jake to direct him to the Methodist church, after which Jake leads him into an alley, knocks him out and robs him. Upon reviving, Drew knocks on the door of the Reverend Clum’s residence, where Mrs. Clum welcomes him and asks him to wait while she delivers lunch to her husband at the church. Meanwhile, Jake meets up with his ragged band of street urchins to examine the plunder they have gathered in their escapades. The homeless boys, consisting of brothers Jim Bob and Loney Logan, Arthur Simms and ten-year-old Boog Bookin, have banded together with Jake to rob the local citizenry and pool their ill-gotten gains to finance a journey West. Upon counting the boys’ paltry take, Jake decides to raise more money by returning the purse that the boys have stolen from Mrs. Clum. Approached by Jake just as she is leaving the house, Mrs. Clum asks him to wait inside until she returns. When Drew sees Jake in the Clums’ kitchen, he pounces on him, and in the ensuing scuffle, the boys throw each other around the kitchen, demolishing the Clums’ cabinets in the process. When Drew demands the return of his stolen money, Jake tries to cajole him into joining his gang. Drew refuses until Mrs. Clum returns, prompting the boys to survey the ravaged kitchen and flee. Back at the camp, Jake presents Drew to the others, but Loney insists that Drew prove himself by robbing a store. Drew, who has sworn to “keep straight and narrow,” takes twelve dollars from the money in his boot, rips his shirt and makes up a story about robbing a hardware store. Some time later, as the boys head West across the prairie, they come upon a homesteader driving a wagon who, after warning the boys to go back East, offers them the sexual services of his female traveling companion, Min. When Drew, who has been taught to save his virginity for his wedding night, demurs, Jake is shocked. Later that night, as they sit around the campfire, Drew, the only literate one in the group, reads to the other boys. After the others have gone to bed, Jake comes to take over the night watch from Drew, who lends Jake his treasured watch so that he can tell the time. Jake falls asleep, however, and the next morning, as the boys slumber, a gang of outlaws led by Big Joe Simmons robs them of their provisions and paltry supply of cash, but Jake manages to conceal Drew’s watch from the thieves. Discouraged, hungry and beginning to doubt Jake’s leadership ability, the boys come upon a farm, which Jake decides to rob. However, when the boys are met by the farmer wielding his shotgun, Drew quickly proposes trading Boog’s pistol for some food. The farmer grudgingly sets a table for the boys, but when he glowers at them as they eat, Jake challenges him, prompting him to run them off the farm. As Drew tries to make peace among the angry boys, Jake spots a stagecoach approaching on the horizon and proposes robbing it. Although Drew objects and refuses to take part, Jake assigns Arthur to run out and flag down the coach while the others lie in wait. Jake and the boys watch incredulously as Arthur stops the coach, climbs onboard and rides off in it. Soon after, the boys come upon a farmhouse, and when Boog steals a pie cooling on the windowsill, the inhabitants begin firing, killing Boog with a bullet to the head and wounding Drew. Rebelling against Jake’s inept leadership, Loney and Jim Bob pull out their guns and announce they have had enough, then ride out with Jake and Drew’s horses and Drew’s watch. Left with only a mule, Jake and Drew plod on along the trail, and soon find Loney and Jim Bob’s bodies hanging from a tree, the victims of Big Joe and his gang. Nearby, Big Joe and the others have just settled down for dinner when they spot Jake and Drew in the distance. Although Big Joe refuses to interrupt his meal, the others ride out to confront Jake and Drew. When Drew asks about his watch, Hobbs, one of the gang, antagonizes him by dangling it from his hand. To outwit the outlaws, the boys start firing at them, chasing them into the woods where they are able to take cover and kill them. As Drew goes to reclaim his watch, Jake spots his money peeking out of a hole in his boot. Enraged that Drew has been holding out on him, Jake knocks him out and takes his mule and money. Vowing to kill Jake, Drew is trudging through the prairie wasteland when he sees a barn burning in the distance. Upon reaching the farmhouse, Drew discovers the marshal and his posse interrogating a member of Big Joe’s gang. The man is to hang for killing the farmer, but before the execution, the marshal urges him to reveal where the rest of the gang is hiding. After the man directs them to an abandoned house, Drew asks him if Jake has joined the gang. When the man nods yes, Drew asks to join the posse. At the renegade’s hideout, the posse opens fire, killing all the outlaws except Big Joe and Jake, whom Drew personally captures. Jake and Big Joe are sentenced to be hanged the next morning, but when Drew confronts Jake about his duplicity, Jake points out that Drew lied to him about the hardware robbery, and reminds him that he refrained from stealing his watch. Forgiving Jake, Drew tries to convince the marshal to spare his life, but when the lawman remains unconvinced, Drew unties his friend and they ride out together under cover of night. After camping for the night, Drew awakens to see that Jake is about to ride off without him. After Drew pulls out his gun and demands that Jake return his money, the two realize that they have become kindred spirits and so ride to the next town, where they enter the Wells Fargo office and declare “stick ‘em up.”