The finale episode of The Winchesters season 1 saw Dean meeting a multiverse version of his parents and saving the day, but it also featured special appearances by some Supernatural actors including Jim Beaver and Alexander Calvert.
Showrunner Robbie Thompson revealed that each writer had their own legacy characters that they wanted to include, but for him, the first name he wrote down was Bobby Singer as he had been in every season of Supernatural and was a significant character in Sam and Dean's lives. The future of The Winchesters is uncertain, but there is an openness to multiverse storytelling and the possibility of shorter and focused spinoffs to keep the saga of The Winchesters alive.