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.
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.
Carrying a bag full of samples, Mitsuo makes rounds to shoe stores in remote cities. While staying at budget hotels, his thoughts turn to Tora-san.
Tora-san visits Hokkaido and is reunited with Lily. Now divorced, she plans to resume her singing career and renews her unusual relationship with Tora-san.
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.
When Tora-san's infatuation with his nephew's school teacher causes family turmoil, he leaves on his travels again. When he returns, he falls in love with the teacher's mother.
Tora-san befriends the descendant of a feudal lord. The man asks Tora to locate his deceased son's wife who resides somewhere in Tokyo.
Tora befriends a pretty barbershop owner and runs into Izumi. When Tora twists his ankle, Mitsuo comes to care for him and see Izumi. Meanwhile, Izumi must choose between her new job in Tokyo and returning to Nagoya to care for her mother.
When cabaret singer Lily writes Toraya about her illness, Tora-san rushes to Okinawa to be by her side.
Tora-san's nephew Mitsuo is exchanging letters with Izumi, a former classmate whose parents divorced and took her out of Tokyo.
Tora-san becomes friends with Toraya's newest tenant, a pachinko-playing electrician that goes by the nickname Watt. Tora attempts to match Watt with a young waitress.
Tora-san leaves Shibamata once again after an argument with his family and finds himself at an inn where he meets Tomekichi, a young man who looks up to Tora-san.
After a chance encounter with Hiroshi's father on a bus, Tora decides to get serious and reflect on the mortality of man. His plans are derailed when a beautiful lady starts working at Toraya.
Tora-san helps out a runaway bride.
Tora-san, an itinerant peddler who is thrown out of his father's house twenty years before but reconnects with his aunt, uncle and sister Sakura. Tora wreaks some havoc in their lives, like getting drunk and silly at a marriage meeting.
On the road again, Torajiro meets a kindred spirit in Lily, a lounge singer.
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.
In Shibamata, Tokyo, Tora-san's family prepares for a wedding. Meanwhile, the traveling Tora-san meets an old acqaintance in Iwate Province. Tora-san refuses to drink with him, afraid that the acquaintance, now settled and married, will again become attracted to Tora-san's wandering existence. Tora-san becomes attracted to a female barber, but must break off their relationship so that she too can live a secure life. She instead gets into an abusive relationship with a motorcyclist.
In Nagasaki, Tora-san and an acquaintance help an old woman who has fallen and injured herself. She invites them to her home where the three share a night of eating and drinking. The old woman's health deteriorates and she dies. At her funeral, Tora-san falls in love with the old woman's daughter, but winds up acting as a go-between for her and a young law student.