Little Bear tells his parents a bedtime story about the first time he met Owl when he was looking at the moon and they shared their interests in the nighttime.
Having caught nothing, Little Bear, Owl and Duck sail out on the lake. In the middle of a storm, a whale swallows them and they escape out of the blowhole.
Little Bear meets a young raccoon who mimics his actions, getting the name Little Little Bear. Together they play games until the raccoon family arrives.
On a hot day, Little Bear imagines himself and Duck lost from the North Pole. After a lot of fun in the snow, they go back to the warmer summer outside their imagination.
Father Bear and Mother Bear are pretty busy and Little Bear gets tired of waiting. Eventually Little Bear teaches Father Bear what it is to be patient.
This morning Little Bear doesn't get up at first, but then he pretends he is the Sleepy Head Monster. When his parents play the game they get tired and fall asleep in Little Bear's bed.
When Little Bear wakes up on the wrong side of the bed, he decides to do impractical opposite things. Little Bear's friends quickly get the idea and play along.
Little Bear, Duck, Owl and Cat attempt to find Little Bear's lost lucky clover. Later he realizes that his luck isn't within a clover, but is in the friendships he shares.
Little Bear practices playing the flute being taught a lesson by Grandfather Bear. The music gets the attention of some mice in the attic and Little Bear and Grandfather Bear lead out into the forest.
Finding nobody at home and lacking company, Little Bear begins talking to himself, to the great astonishment of his friends. When he finds them hiding in a bush he rejoins them.
It's bedtime, but Little Bear wants to ensure he stays awake. After some excitement, Little Bear and his parents finally get tired enough to go to bed.
Little Bear tries to get Father Bear to stay in a perfect posture for his picture, but Father Bear is in a silly mood. Still Little Bear gets his picture done.
As Mother Bear prepares the table for Harvest Day, Little Bear breaks her gravy boat. Little Bear's friends try to fix it, but Father Bear has the answer.
Little Bear tries hard to catch a dandelion fluff to make a wish. Duck and Cat assist him hoping for a share of the wish until they all run into a field of dandelions.
An octopus takes Fisherman Bear from Little Bear. With Mermaid's help, Little Bear retrieves him from the Octopus' tea party and finds him a new friend.
Grandfather Bear has lost his pocket watch. Little Bear sums up some clues to conclude a goblin took it, but at lunch he finds it hidden in a loaf of bread.
As Duck tries to teach the ducklings how to quack, she loses her own. Wherever they look, the ducklings pick up other noises. Duck finds her quack when Little Bear tries.