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Teenaged troublemaker Henry Aldrich smashes a boat he borrowed without permission while showing off for his friend Dizzy Stevens' girl friend and her cousin. Mr. Weeks, who runs the boating operation, forces Henry to sign a confession and insists that he will arrest Henry if he does not pay him $120 or get him a new boat in two days. Henry does not confide his troubles to his parents but does ask for his father Sam's help in building an outboard motor. When his father refuses, Henry panics and convinces Dizzy and their friend, Phyllis Michael, to raise the money. They first try to sell some junk to second-hand dealer Joe McGuire, but end up exchanging it for an old-fashioned vacuum cleaner. Unable to unload the vacuum on Dizzy's father Frank, an appliance salesman, Henry and Dizzy go door-to-door trying to sell a cleaning service. Mrs. Bradley lets them in her house, but the ancient machine wreaks havoc in her living room and the boys are terrified to learn that she is their high school principal's wife. On the way home the vacuum gets loose from their jalopy, and both the car and the vacuum crash into McGuire's shop. Henry and Dizzy's parents are fined for their children's antics, and Henry's father, who is fed up with his son's innate ability to cause trouble, warns Henry that he will no longer help him out of his troubles. The problems have also caused a rift in the friendship between Sam and Frank, and when Phyllis, in an effort to help Henry, spreads false gossip that each man is insulting the other's athletic prowess, both men attend the Independence Day picnic and compete in the father-son races to win a boat. Although the competition between the Aldriches, the Stevens and the Weeks is tough in the various relay races, Weeks is disqualified for losing a baton and Henry and Sam win the boat. Weeks confronts Sam about the money that Henry owes him, but when Sam points out that the confession was signed under duress, Weeks's son Billy unintentionally reveals that the insurance company has already paid them for Henry's mishap with the boat. Sam hits Weeks for his duplicity, and Henry takes his friends for a ride in his new boat and accidentally takes the dock with him.