Sister Bear, nervous about entering kindergarten, overcomes her fears when she discovers that school is really fun.

Big Brother helps Milton Chubb, a huge new cub, deal with the school bully and make friends with Bertha Broom, but then Milton and Bertha must meet in a match for a spot on the school's wrestling team.

Sister Bear dislikes gym class so much that she takes advantage of a minor injury and sits on the sidelines instead.

Mr. Dweebish, the new teacher at the Bear Country School, tries to explain to the class bully how democracy works.