Little Raccoon has adventures fishing by himself at night, venturing into the outside world beyond his woods, and babysitting two tricky chipmunks.

Little Raccoon has a question. It is a question for his mother. "When do you love me most of all?" he asks. Of course, one question leads to another. "Is it when I wake up?" And another. "Is it when I play in the trees?" And another and another and another. Little Raccoon has lots of questions. How many answers does his mother have? Just one.

Little Raccoon grew up under the love and protection of his mother. They lived in a hollow tree and played in the fields of flowers. She taught him all he needed to know to grow healthy and safely within their part of the world. But as Little Raccoon grew, he found it more and more compelling to explore farther and farther from the protection and safety of his home. When Little Raccoon comes upon some other raccoons playing in the meadow, he wanders past his boundaries on the quest to find independence and freedom.

Wally Raccoon worries about making his first trip to school alone as he examines all the possible pitfalls.