Sherman is a sweet, lighthearted little caterpillar with a big dream. Sherman dreams of flying. Deep down in his big heart, Sherman knows he's meant to fly even though he has no wings and his rows of legs are made only for walking. As he looks upward toward the sky one day, he catches a glimpse of a beautiful monarch butterfly and thinks to himself, "That's going to be me someday."

But the other bugs are sure that Sherman is out of his mind. How could a chubby, crawling caterpillar ever leave the ground and fly? They tease and ridicule poor Sherman relentlessly, saying anything they can to try to dash his precious dream. But Sherman just might be tougher than any of them think. Despite the unkindness of his peers, Sherman tries to hold on to his dream of flying.

Intending to prove them all wrong, Sherman climbs high into the branches of a very tall tree one sleepless night. Will Sherman's faith be enough to help him fly? Or could he be forgetting something?