Jack Carter, a modest, middle-aged man, and owner of a bakery has found himself and his family in a rut. Not only can he not provide his family with the finer things, he has also found he is not as close to his kids as he would like to be. So for the upcoming Christmas holiday, Jack has the brilliant idea to reconnect with his family while also trying to spark his desired career in writing by going on a Christmas vacation to a cabin resort in the mountains where his late father used to take him as a boy. From the get-go, however, the trip seems to be doomed: their cabin is a dilapidated disaster, the kids are constantly complaining, and then... Jack runs into his estranged, ubercompetitive friend, Robert, who seems to upstage Jack at every turn. Feeling dejected, Jack plans to finally one-up Robert at the very games Robert used to beat him in so long ago as kids: The Farthing Pines Winter Olympics a series of events that Jack's dad came up with. Will Jacks plan save this family vacation after all?