Kevin is a model train enthusiast who has always been fascinated by the town's old North Pole Express train line. One day, he reconnects with his former classmate Danielle, who is home for the holidays with her young son. Together, they decide to take on the challenge of resurrecting the old train line for the holiday season.
As they work on the project, Kevin and Danielle reminisce about their childhood memories and catch up on each other's lives. Kevin begins to see Danielle in a new light, and he starts to fall for her. However, he is hesitant to reveal his feelings as he doesn't want to jeopardize their friendship.
Meanwhile, they run into several obstacles, including funding and permission from the town, as well as finding the necessary equipment and resources. With the help of a few dedicated friends, they push through these challenges and make their dream a reality.
The train line is finally ready for its inaugural run on Christmas Eve. The entire town turns out to witness the event, and Danielle's son is thrilled to ride on the train. Kevin finally musters the courage to confess his feelings to Danielle, and they share a romantic moment as the train chugs along the track.
Toying with the Holidays is a heartwarming holiday movie that celebrates the joy of community and the magic of love during the festive season.