A small-town teacher relocates to one of the country's toughest classrooms.

Five Halloween stories: A principal has a secret life, a virgin is looking for her first time, a group of kids pull a prank, a woman who loathes Halloween does not respect the rules and a mean old man meets a demonic trick-or-treater.

Jack Clayton can only escape after his partner in crime Harry Zordich messes up a Christmas sales department store robbery in a Santa suit. Stuck in a rural small town, he finds himself forced to accept a menial job under the alias Oscar Burton as Santa in Sarah Gibson's nursery. Jack relaxes when invited in their home and proves a good substitute father for Sarah's frustrated fatherless daughter Noelle. Widow Emily Sutton's nostalgic Christmas shop completes his nostalgia, and becomes crucial when his ex-con cahoot turns up to plan a bank robbery. Sarah's admirer keeps warning the sheriff against 'Oscar', who meanwhile teaches the town how to fight off competition from the city mall.