Jake Myers fights to save a struggling Main Street Wintergreen. As businesses and even the city have largely turned their back on the once-thriving downtown marketplace, Jake tries to unite the community in celebrating Christmas together in the classic ways that had made Wintergreen such a special place.

Bea Bailey, owner of the Coffee Corner, one of the businesses Jake is working hard to save, pushes her granddaughter, Sara, to work closely with Jake. As Jake and Sara rally the town and reignite lost Christmas traditions, the pair realize they have a lot more in common than trying to save her grandmother's café.

Sara's old high school flame and Jake's on and off again girlfriend dash any romantic sparks nearly as soon as they have a chance to catch. Making Jake's holiday season more complicated, his girlfriend's father is the head of his marketing firm which has staked Jake's future on a game-changing account with impossible deadlines.