The film has several intertwined plot lines: One story is about a driven, workaholic lawyer named '''Robert Layton''' and the impact of his job on his marriage to '''Kate''', and to his relationship with his daughter '''Lily'''. Another is about Robert's mother '''Ellen''', and her friendly neighbor '''Dalton''' who is a teacher at Nathan and Lily's school. The main story is about '''Maggie Andrews''' and her terminal illness, and how her family (small businessman husband '''Jack''' and young son '''Nathan''') deals with the impending loss. All stories are linked together. The story opens with Robert visiting the cemetery shortly before Christmas. He sees a younger man wearing a Boston Red Sox Cap visiting another grave. We flash back...
Nathan Andrews, a medical resident, goes back home to his small town after he loses a teenager on the operating table. He joins his dad and his mechanic's business and becomes a basketball coach to some youths. Here he meets Charlie and Meghan. This is based on a novel by Donna VanLiere and a continuation of "The Christmas Shoes." Meghan is trying to start up a day care business for single, working mothers and Charlie is ill. All their lives are connected and Nathan meets someone from his past.
After the recent loss of her son Sean—a minor character in ''The Christmas Blessing''—Patty Addison (Madeleine Stowe) devotes herself to finding homes for needy children. The loss of Sean has strained Patty's relationship with her husband Mark, an airline pilot. But they reconnect emotionally when they take in Emily, a 9-year-old orphaned in a car accident similar to the one that killed Sean.