Ivy dreads the holiday season. But this year promises to be even worse as her brother, and only family, will not be returning home for the holidays. Ivy is doing her best to avoid all festivities. But with the tree lighting, a holiday homes tour, and the downtown businesses door decorating contest, it's hard to skip the holidays in Cranberry Bay. Meanwhile, after his grandfather dies, Josh must step into Cranberry Bay's beloved holiday tradition to drive the Holiday Express Christmas Eve train. When he asks Ivy to play the role of Mrs. Claus neither expects their long-time friendship to turn into love.