It's been an unusually mild winter in Syracuse, New York, much to the dismay of ten-year-old Natalie Brandston (ZENA GREY) and her friends Wayne (JOSH PECK) and Chet (JADE YORKER). That's because their arsenal of snowballs from last winter has just been depleted and they have yet to enjoy a snow day that would close their school.
Natalie's fifteen-year-old brother, Hal (MARK WEBBER), has other things on his mind. Despite the advice from his friends Lane (SCHUYLER FISK) and Bill (J. ADAM BROWN) that he doesn't stand a chance, Hal is determined to ask out Claire Bonner (EMMANUELLE CHRIQUI), the girl of his dreams. The only problem is she doesn't know he exists and already has a boyfriend, Chuck Wheeler (DAVID PAETKAU).
When he finds Claire's ankle bracelet and hears that she's just broken up with Chuck, however, Hal decides it's time to make his move. Even so, a sudden, crippling snowstorm briefly impedes his efforts, just as it does for his workaholic mother, Laura (JEAN SMART), who simultaneously tries to cope with work and her adventurously hyperactive, four-year-old, Randy (CONNOR MATHEUS).
Of course, the snowstorm didn't come as a surprise to Tom Brandston, the family patriarch and local TV weatherman. Nonetheless, he must contend with his boss Tina (PAM GRIER) who continually tries to think up on-air gimmicks for Tom so that he can catch up to rival weatherman Chad Symmonz (JOHN SCHNEIDER) in the ratings.
For Natalie, the snow day is a welcomed answer to her wishes, but she and her friends then find that they must contend with their dreaded enemy, Snowplowman (CHRIS ELLIOT), and his huge snowplow, Clementine. While the determined girl and her friends try to stop Snowplowman and thus ensure their first consecutive snow days in history, her mom tries to get her work done, her dad attempts to prove that his competitor is a fraud, and Hal hopes to win Claire's heart despite being blinded to the fact that it's really Lane who has a crush on him.