During Halloween, there are jack-o-lanterns placed all around campus. If Jimmy destroys all of them, he earns the pumpkin mask that Lucky wears, and a trophy for his room.
If Jimmy doesn't destroy the pumpkins, they will appear in the school basement and can be destroyed during or any time after Help Gary.
The tombstones appear immediately after The Candidate ends, but before Halloween actually starts. As the clock disappears after The Candidate, Jimmy has plenty of time to look for them.
If Jimmy has not smashed all the tombstones by the end of The Big Prank, he can find them inside the Spencer Shipping Warehouse during Chapters 5 and 6.
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