Traveling salesman Kuruma Torajirō falls in love with an inn manager as New Year's approaches.
Taking a message from Hiroshi's father to heart, Torajiro attempts to give up his wandering ways.
While Sakura and Hiroshi struggle to save funds to build a house, Torajiro befriends three young women on vacation during his travels.
After a quarrel with his mother, Torajiro sets off to find a bride.
When his travels take him to rural Hokkaido, Tora-san helps a cantankerous old veterinarian (Mifune) in his relationships with his estranged daughter, and a woman in whom he is secretly interested.
Tora-san's opinions about Americans get challenged when another wandering peddler Michael Jordan stops by Shibamata.
After an encounter with a dying yakuza's son and at his sister Sakura's urging, Torajiro attempts to change his vagrant lifestyle and become an honest worker with a steady job.
Torajiro becomes homesick during his travels after watching a television report about his hometown and meeting a young woman that reminds him of his sister Sakura. Meanwhile, a new tenant moves into Toraya restaurant.
Tora-san spends several days at the home of a hard-working salaryman ("salaried worker"), who abruptly disappears. When the man's wife asks Tora-san to help find him, he falls in love with her, and secretly hopes the husband will not be found.
Tora-san is inspired to pursue an education after a visit to the grave of a woman he met years ago. When he returns to Shibamata with the intent to study, he falls for Toraya's new tenant instead.
After Torajiro's latest attempt to find a bride goes awry, he starts traveling again and runs into Utako (last seen in Tora-san's Dear Old Home), now a widow.
After Hiroshi is injured in a workplace accident, Torajiro gives Sakura the money he has saved and leaves to work as a traveling salesman once again. During his travels, Torajiro meets a father who shares a drink with him. In the morning, Torajiro is shocked to learn that the man has left his baby behind and a note asking Tora to take care of the child.
After a friend and business colleague dies, Tora-san visits the man's daughter, then takes her to Tokyo so she can study for a night school exam.
When his travels bring him to Osaka, Tora-san falls in love with a local geisha. He helps her to track down her estranged brother, and informs his family that he plans to marry her. His plans are foiled when the geisha informs Tora-san that she is engaged.
During his travels, Tora-san gets drunk with an old man in Kyoto. Though Tora-san never fully comprehends his importance, the old man is a Living National Treasure ceramist. At his home, Tora-san makes a good impression on the old man's maid, who apparently falls in love with Tora-san.
Tora-san gets into an argument with his uncle and sets out on the road again. In Kyushu he meets a young woman named Keiko and the shy zoologist Saburō, and attempts to play matchmaker between the two when they all return to Tokyo.
Tora-san returns to his family home to learn that his brother-in-law cannot go to Mitsuo's (Tora-san's nephew) athletic event. Tora-san volunteers to take his place, but gets into an argument with his brother-in-law's boss and returns to the road. He meets a young woman in Niigata who, unbeknownst to him, is a popular enka singer.
During his travels, Tora-san comes across a traditional theater he used to visit, and discovers that one of his old friends has died. Tora-san and his family help the friend's daughter, who becomes romantically involved with an aspiring artist.
A playboy-gambler friend of Tora-san’s dies and, abandoned by his mother, his little boy suddenly turns up in Shibamata. Searching for the boy’s mother, Tora-san meets a cosmetics saleslady and the three become a surrogate family, with Tora-san as “daddy”.
In his travels through Japan, Tora-san meets and falls in love with a female doctor, however he is afraid of committing to a relationship.