The novel The Wednesday Wars is organized into months, spanning the whole of Holling's academic year from September to June.

In October, for the sake of his father's job, Holling behaves in a quiet, helpful manner with Mrs. Baker, keeping the chalk boards and the coat room clean. He carries trays of pastries for her up from Mrs. Bigio's kitchen, but then he accidentally lets the dust from the erasers he's cleaning float up and settle on the pastries, which ruins them. Because the chalk dust just looks like sugar, no one notices until they try to eat them, and Holling never actually gets in trouble for this incident.

Holling's sister, though, gets in trouble with her parents for trying to be a "flower child" who protests the Vietnam War, and Holling's friends get angry at him for being the only kid who got to take one of the cream puff pastries from the trays he carried. They don't realize that Holling didn't actually eat the pastry. He knew it had chalk dust on it.

Mrs. Baker decides to make Holling read Shakespeare with her instead of doing chores. But before they start, Holling has to clean the pet rats' cage--and he accidentally lets them loose and they both escape into the walls. The school staff makes Holling swear to keep the rats' escape a secret from the other students (presumably so they don't go nuts about it).

Holling and Mrs. Baker then read Shakespeare's The Merchant of Venice, which Holling assumes will be boring, but he actually enjoys it.