Determined to win a trophy of some kind, first-grader Roscoe swaps a hand-knitted sweater from his grandmother for the chance to enter his new neighbor's very clever dog in a trick contest.
When first-grader Roscoe discovers that his stuffed pig is missing from his backpack, he accuses the class bully of "pig-napping" and gets even by taking the bully's teddy bear.
Roscoe is determined to guess the weight of a giant pumpkin in order to win books for his school library and candy for himself, but is overwhelmed by superstitions, especially about a certain black kitten.