Sam tries to move on without his brother and becomes hardened and more reckless in the way he hunts. Bobby and his psychic friend Pamela try to contact the other side to find out more about Dean's ultimate fate.
Castiel sends Dean back in time to 1973 where he encounters younger versions of his parents and for the first time meets his grandfather Samuel Campbell who holds a secret that sheds a light on the Winchester Family's connection to the hunter community.
A hunter named Travis points Sam and Dean towards a meat eating creature called a Rugaru. Complicating matters is the fact that Travis's target is a normal suburban dad in the earlier process of changing and he hasn't killed anyone yet.
It's Halloween time and the Winchesters face-off against a shapeshifter with a penchant for impersonating classic movie monsters like Dracula, the Wolfman, and the Mummy.
Hell beckons again when Dean is stricken with a mysterious illness that frightens its sufferers to death. Sam and Dean scramble to find the cause of the disease in time to save Dean from sure death.
Investigating two mysterious deaths in a small town, Sam and Dean discover a witch is sacrificing people to summon an ancient powerful and extremely dangerous demon.
Sam, Dean, and Ruby discover the existence of a female prophet named Anna Milton, who can hear the voices of angels and thus figures into the plans of a demon named Alastair who wants to use her as a tool against the angels.
"I'll Kill her gentle." The angels want Anna dead, so Sam and Dean go on the run with the frightened girl, determined to discover the secret that has set the furies of Heaven on her.
Castiel and Uriel ask Dean to torture Alastair for information. But when Alastair breaks free, Castiel starts to believe that there is a traitor among the angels.
At Sandover Bridge & Iron Inc., Dean is Dean Smith, the buttoned-down director of Sales & Marketing. Sam is Sam Wesson, a cubicle-dwelling tech support guy. What the heck is going on? Or is it what the Hell?