The Winchester Brothers Finally "Carry On" to Their Final Adventure in Supernatural Finale

Though the brothers saved the world in the penultimate episode, Sam grapples with his grief at the beginning of the final episode. While the brothers are free from Chuck's machinations, they've lost Cas and Jack, the other halves of their family unit. When Dean attempts to bring some joy in their lives with a Pie Fest, their good times are interrupted by a home invasion that leads them to a vampire nest. While trying to rescue two young boys taken to the vampires' vest, the hunters are quickly outnumbered and meet a homicidal blast from the past — Jenny, a young woman who was turned into a vampire way back in season one. Sam is able to dispatch Jenny and while fighting back the other vampires, Dean is impaled through the back by a spike jutting out the wall. Dean says goodbye to Sam, asking his brother not to try and bring him back, asking him to let him go.

Left alone with Dean's dog, Sam burns his brother's body and returns to the Men of Letters bunker. He receives a call on Dean's phone about a hunt in Austin, Texas, and decides to leave the bunker, start his own life. As Dean revels in his afterlife, Sam appears with a little boy seemingly named Dean and a woman, having created his own life. He lives well into his old age where he dies with his son by his bedside. In the afterlife, he's finally able to reunite with Dean.

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 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 that he was always proud of Sam. He asks for Sam to tell him it's okay 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.