Plot

Depressed single mom Adele and her son Henry offer a wounded, fearsome man a ride. As police search town for the escaped convict, the mother and son gradually learn his true story as their options become increasingly limited.

A depressed mother's husband has left her for she could not bear a second child. Living alone with her only son, she has an unlikely meeting with an injured escaped convict, and reluctantly takes him into her own care. The man proves to be better than his criminal image as the three bond over Labor Day weekend. The only problem? Everyone in town is looking for him.

As the twosome shop for clothes Henry will wear when he begins seventh grade after the long Labor Day weekend, the boy is accosted by Frank (Josh Brolin), an escaped convict with a bleeding wound on his stomach. Frank manipulates Adele into letting him hide out at their house, and soon the seemingly scary man shows a strong domestic side and, in just a few days, develops a deep bond with both Adele and Frank..

In 1987, Adele Wheeler (Kate Winslet) is a depressed single mom who lives in a rural home with her 13-year-old son, Henry (Gattlin Griffith). While they are clothes shopping, a bloody man approaches Henry and makes them take him home to look after him. The man is revealed to be Frank Chambers (Josh Brolin), a convict who is wanted by the local police after breaking out of jail. Through flashbacks, it is revealed that Frank is a Vietnam veteran who returned home and married his pregnant girlfriend, Mandy (Maika Monroe), who soon gave birth. A year after the baby's birth, Frank and Mandy had a fight, in which, based on his suspicions he asks if he's even the baby's father. During the fight, he pushed her against a radiator, resulting in her death. Simultaneously, through imagery, it is implied that the baby drowned. Frank was sent to jail for murder.

It is also learned as Adele tells Frank through flashbacks that she has had pregnancy losses after Henry, including a number of miscarriages and finally, the full-term stillbirth of a baby girl. This has left Adele with significant psychological issues including severe social anxiety and depression, which Henry's father later explains to Henry as the reasons behind leaving her. Henry has tried to be both a son and a husband (innocently) but he realizes he can't provide all of the things Adele needs. Adele is a passionate woman who loves to dance and teaches both Henry and Frank separately to dance. Frank teaches Henry car repairs and other handyman/fatherly things. He also teaches Adele and Henry how to play baseball and how to bake a peach pie.

Adele and Frank fall in love and plan to escape to Canada with Henry. They begin packing the house and cleaning on Labor Day. Meanwhile, Henry develops a friendship with a mature, but manipulative girl named Eleanor (Brighid Fleming), and goes to see her one more time before they leave. She manipulates him into thinking Adele and Frank are going to abandon him and he accidentally reveals Frank's past. Adele assures Henry, she would never leave him. The morning they are going to leave, Henry takes a note to his father's house and leaves it in his mailbox.

While he is walking home, a policeman (James Van Der Beek) offers to drive him home, and Henry has no choice but to accept. The policeman is suspicious of the packed car and nearly empty house, but eventually leaves. Adele goes to the bank to get all the money out of her account, and the bankers too are suspicious. While Adele is gone, the neighbor comes over to give Adele some cinnamon rolls and speaks to Frank. She, too, is suspicious of who he may be.

Henry's father finds the note that Henry left and calls the house wondering what is going on. Before Adele, Frank, and Henry can escape, they hear police sirens headed toward their house. Frank ties Henry and Adele up before he goes out to surrender, so that they won't be charged with harboring a fugitive. The police arrive and arrest Frank. It is not revealed who called the police to report Frank's presence at the house.

Years later, adult Henry (Tobey Maguire) has become the owner of a pie shop and is contacted by Frank, who is getting out of jail. Henry tells him that his mother is still single, and Adele meets Frank at the prison upon his release. Adele and Frank in the Autumn years of their life walk in love and Henry takes solace in the fact that he won't have to worry about her being alone.