Based on Sally Benson's autobiographical novel, a lawyer's family finds romance and does not want to move to New York.
In the summer of 1903 Esther Smith (Judy Garland) and the maid Katie (Marjorie Main) arrange an early dinner so that Rose Smith (Lucille Bremer) can receive a proposal on the phone. Esther is eager to meet her new neighbor and sings "The Boy Next Door." Lawyer Alonzo Smith (Leon Ames) insists on a bath and a later dinner because they say the reason is Katie. During dinner Rose gets a call from New York but no proposal. They have a party, and Esther meets John Truett (Tom Drake). They all sing "Skip to My Lou" and dance. Little Tootie Smith (Margaret O'Brien) comes downstairs in her nightgown and with Esther sings "Under the Bamboo Tree." Esther asks John to help her turn out the lights and sings "Over the Bannister." Going to the fairground, Esther sings "The Trolley Song.
On Halloween, Tootie and Agnes Smith (Joan Carroll) go out in costumes, and Tootie throws flour on the hated Mr. Braukoff. Rose is brought home by a man who does not come in. Tootie is hurt and says John tried to kill her. Esther goes after John and tries to fight him. Tootie and Agnes admit they played a trick on the trolley. Esther apologizes to John, who kisses her. Alonzo says he is being promoted and transferred to New York; but no one else wants to move, and he feels like a criminal. His wife Anna Smith (Mary Astor) says they will go with him. Alonzo sings "You and I" with Anna.
On Christmas Eve, Esther persuades her brother Lon Smith (Henry H. Daniels Jr.) to take Rose to the ball. Rose helps Esther get into her corset. John comes over and tells Esther that his tuxedo is at the closed tailor's. Grandpa (Harry Davenport) offers to take Esther to the ball. Lucille Ballard (June Lockhart) puts Warren Sheffield (Robert Sully) with Rose and goes with Lon. Grandpa dances Esther over to John. Esther agrees to marry John, who says he will not go to college but work to support her. Esther sings to Tootie "Have Yourself a Merry Little Christmas." Tootie knocks over her snow people because she does not want to go to New York. Esther consoles her as their father Alonzo watches from the window. Alonzo calls the family together and says they are not moving to New York. Warren comes in, orders Rose to marry him, and then leaves. The family celebrates Christmas. In the spring they go to the World's Fair.
This musical celebrates an earlier era and the joys
of living in a large family in the same town without having to