After the ball they're playing with gets ruined, Herbie Bear and his friend Michael must find an alternative. In their attempts to trade items for Herbie's younger brothers' ball, the boys learn a lesson in sharing.
Herbie Bear learns skateboarding tricks from the new kid in the neighborhood.
Herbie Bear loves storytime at his library, but spends more time asking questions than he does listening. He must learn to sit quietly to hear his favorite stories.
Herbie Bear struggles with math problems, but learns to take his time, raise his hand, and answer correctly.
Herbie Bear loves to paint, but learns that some things are better off left as they are.
Herbie Bear is scared to go underwater, but an imaginary adventure gives him the courage he needs.
Herbie Bear and his siblings and friends decide to build a fort, but must learn to cooperate and share their items to get the job done.