He suffered from cancer of the esophagus, diagnosed in 2011, and died at his Virginia home. Winchester relocated to Montreal in 1967 after receiving his draft notice, and played in small folk clubs in the city until an audiotape of his work was noticed by Robbie Robertson of The Band. A self-titled album followed in 1970, and is regarded by many as Winchester’s best work.
He played his first concert in the United States in 1977 after President Jimmy Carter declared an amnesty for draft resisters. He moved to Virginia in 2002.
Winchester, regarded as a premier songwriter, had his songs sung by artists including the Everly Brothers, Emmylou Harris, Wilson Pickett, Joan Baez, Lyle Lovett and Anne Murray.