After listening to Oswald play his piano, Daisy wishes she could play an instrument, so Oswald takes her to the music store, where she tries out different instruments.
A ball of red yarn is Weenie's favorite toy. When it begins to bounce, Oswald accidentally grabs a string of the yarn, making it unravel out of his apartment all the way out through the city. Oswald and Weenie chase after it as it entangles several of their friends along the way.
Oswald cleans his apartment, but it did not turn out good. So Oswald decided to put the things he no longer needs in a wagon to take to the dump, but several Big City citizens find uses for them.
Oswald builds a birdhouse and adds some color, some flowers, and some bells to it. But a rain advisory washes away the color, flowers, and bells, making the birdhouse look plain, which the birds like.
Henry has a feather sticking out on top of his head, but his feather will not stay down. He is scared to go to the barber because he keeps thinking the barber is too scary.
Oswald buys a pet fish that he names Flippy because of the flip that she does, jumping out of her bowl and splashing back in it. Unfortunately, Flippy keeps overeating and growing bigger and bigger. So Oswald and Weenie take her to the Big City public aquarium, where she becomes a big star at the seal show.
Oswald goes out into Big City to get some cocoa and a newspaper for Henry, who has a bad case of the Arctic Sniffles. But a rain cloud chases Oswald and Weenie until a rainstorm makes Oswald catch a cold.
Oswald is excited to meet Henry's cousin, Louie. But the two penguins have a great time all by themselves. Oswald feels left out, but once Henry and Louie catch up on old times, they seek Oswald out.
After Henry decides to move back to the frozen north with his cousin, the others prepare a going away party for him. In the end, Henry decides to stay in Big City after saving them from being blown away.
Oswald eats his last tomato for breakfast, he decides to get more by planting tomatoes in the garden. Oswald is surprised and upset when he sees one of the tomatoes have been half eaten, and discovers the tomatoes were eaten by an entire group of snails. He ends up making a restaurant for the snails.
Oswald and Daisy make honey buns, but Daisy adds too much sticky honey, and they get stuck to each other, along with other friends and eventually it starts to rain and the friends got unstuck.
The clock in the Big City's bells somehow is not working and Big City is still asleep. It is up to Oswald, Weenie, Henry and Daisy to figure out what is causing this stroking catastrophe to make the clock work again to wake up Big City.