Born in 1949, Winston was raised primarily in Montana. The pronounced seasonal changes he experienced there became the primary inspiration for all the music he would later play. As a child, Winston preferred instrumental music over vocal performances, counting among his early heroes Booker T and the MG’s, Floyd Cramer, The Ventures, jazz organist Jimmy Smith, and many other instrumentalists. He began playing organ in the summer of 1967 after graduating from high school, and switched to piano in 1971, inspired by the recordings of stride pianist Fats Waller. At this time, Winston also created his own melodic folk piano style, which he would become best known for, and soon released his first solo piano album, Ballads and Blues 1972. Among his other popular Windham Hill/Dancing Cat solo piano recordings are Autumn, December, Winter into Spring, Summer, Forest, Linus & Lucy: The Music of Vince Guaraldi, and his September 11, 2001 benefit recording, Remembrance.