Janie Collins is a hard working and talented New York City marketing and branding executive, and while she loves her work, she laments having to work for clients in whose products or services she doesn't believe. This Christmas season, she will be traveling to Woodland Falls upstate to deal with her Great Uncle Randall's estate - she the executor - before she and her boyfriend Charles Miller head to Los Angeles for a week including for the actual day. While she did ask him, Charles has no desire to accompany Janie to Woodland Falls, where she hasn't been since she was ten, as he evaluates all his decisions on how it will best benefit him professionally, he planning to go to Los Angeles early to make some business connections. Janie is surprised by two things in her time in Woodland Falls. First, that Dylan, the older brother of Nicole, her best childhood friend, lives on Uncle Randall's farm as his assistant. And second, that Uncle Randall has left the bulk of his estate to her, including the farm. While moving to Woodland Falls to be a farmer was not on her scope and thus her plan is to sell the farm, she, after some consideration, decides to stay longer until Christmas Eve to honor Randall's final request of her: to organize this year's edition of the Winter Wonderland, a community event which he always held on his property. While Janie can use her professional skills to handle the marketing side of the event, she requires Dylan's assistance to handle many of the local logistics on the farm. In spending time on the farm with Dylan organizing the event, Janie may come to a realization about a different path in life including with who she would really like to spend that life.