Nick, Phil, Owen and Eddie are shocked when they find out that their childhood crush, Angela Ferilli, is dead. They reminisce about the past they shared together and realize how much Angela affected their lives.

Nick and Eddie go to New York to try bringing Owen back to Knights Ridge and his family. Hannah has to deal with her true feelings for Nick.

A visit from Eddie's ex-girlfriend Rory causes problems in his relationship with Janet. Nick receives a great job offer that should take him far away from Knights Ridge. Hannah is arrested for assaulting Ray's ex-wife Christine.

Owen, Nick, Ronnie, Aubrey, Gabriel and the Commander take a road trip to find the girl who saved Owen's life, and The Commander uses the opportunity to remind his sons of their childhood, and to finally be able to tell them about his condition. Nick encourages Gabriel to tell the truth about his upcoming departure to his daughter.

Ray successful ex-wife Christine intimidates Hannah, after she leaves the Cataldo boys in care of an old hippy friend, in order to take a veterinary tech exam. Pizza Girl begs Phil to take her out on a ride with the classic car stored in his garage. Nick sets up Ronnie with Aubrey's friend, but things change when Ronnie realizes he's in love with Aubrey.

Nick is surprised when his father refuses to do the Christmas festivities in the house, and he decides to find a way to learn why. Physical Phil continues his tradition of pretending to be an architect when his parents come for a visit, which irritates his girlfriend. Eddie freaks out when Janet gives him a very personal Christmas gift. Owen and Alison end up in bed, but their happiness as a couple is soon put onto a test.

Janet and Hannah plan a double date, but their boyfriends can't put their differences behind them. Nick's past comes back to haunt him when he tries to bid on a new project with Eddie, and the person hiring is a man named Cupcake Kid. Ikey decides it's time to reach out to his friends, and Owen is having hard time dealing with forgiveness.

A visit from Eddie's ex-girlfriend Rory causes problems in his relationship with Janet. Nick receives a great job offer that should take him far away from Knights Ridge. Hannah is arrested for assaulting Ray's ex-wife Christine.

Hannah shares her feelings with Nick and decides to take her life in a new direction. Eddie is having problems showing his feelings for Janet in public. Nick learns that another professor has taken over his class. Physical Phil is on the verge of losing the only connection to the world outside of his house.

Janet is worried because Eddie and her still haven't slept together. Hannah is put in a tough position when Ray tells her that he wants to adopt Sam. Nick thinks that Aubrey is keeping a secret from him.

Owen tries to deal with his wife's infidelity by sending Nick to learn more about it from Ikey. Sam struggles to accept the fact that his mother is getting married. Eddie has a secret that could ruin his upcoming business venture with Nick.

Hannah is troubled when her parents visit to help her prepare for her wedding. Nick learns he's broke. Owen goes out on a date with Jenny, the girl who saved his life.

The Commander finds out that he is having a health issue. Ray is still trying to convince Hannah to let him adopt Sam. Nick discovers that Aubrey has been secretly visiting her estranged father. Alison and Owen start dating other people.

This is the 10 minute series finale of October Road that was created for the Season 2 DVD release