On the eve of the 1904 World’s Fair in St. Louis, Missouri seems more cosmopolitan and worldly than ever before. The Smith family has four high-spirited daughters, including Esther (Judy Garland) and the precocious and mischievous, Tootie (Margaret O’Brien). New neighbors move in next door. Esther, a perpetual busy-body, finds herself head-over-heels in love with their son, John (Tom Drake). At first, the two are at odds after Tootie pulls a Halloween prank and blames John for attacking her. Esther marches over to confront him, not knowing Tootie’s deception. Mr. Smith (Leon Ames) arrives with an announcement he is being promoted to head a new office for his company and the family must move to New York – after Christmas and before the World’s Fair. This doesn’t seem, well, fair to all the Smith girls, and to love-sick Esther in particular.