Herbie the bear and his friend Michael the raccoon participate in their school's Halloween contest and try to come up with a good idea so they can win.
On a rainy day, Herbie and his siblings learn a lesson about taking turns when their argument over which board game to play distracts their father from reading his newspaper.
Herbie the bear grows nervous as the school's Thanksgiving play approaches and he fears he will forget his lines, but when the day arrives, he surprises himself by performing quite well.
Young Herbie Bear learns about the importance of water conservation and shares his knowledge with his classmates when he presents his science project on ways to save water.