After having Cas die in front of him two episodes before, Dean is fully ready to live his fullest life in memory of the angel. He begins the final episode by finding a local Pie Fest to make his wildest dreams come true, but vampires quickly ruin their relaxation. (Not vamp-mimes.) While battling the vampires in the nest, Dean is impaled through the back by a spike jutting out of the wall. In his final moments, he has what he loved to call a "chick flick" moment and pours his heart out to his brother. He recounts a time he visited Sam without the other Winchester knowing, telling him he was always proud of Sam. He asks for Sam to tell him it's OK to let go, hugging the younger man to him when he gives his "permission" and dying in his baby brother's arms.
When Dean ascends to "Heaven," he's greeted by Bobby, who explains that Jack and Cas have completely changed the way the afterlife works. Instead of just reliving memories, folks get to enjoy their "lives" as they see fit. Which, for Dean, means taking Baby for a drive. By the end, he reaches a bridge, where he reunites with Sam, who's lived a long and happy life.
