When growing up, Winston's interest in music were instrumentals of R&B, rock, pop, and jazz genres, especially by organists. After hearing The Doors in 1967, he was inspired to start playing the organ. In 1971, he switched to solo piano after hearing stride pianists Thomas "Fats" Waller, Teddy Wilson, and later Earl Hines, Donald Lambert, and Cleo Brown.
Winston attended Stetson University in DeLand, Florida, in the 1960s, where he majored in sociology. While he did not complete his undergraduate degree, following his rise to prominence the university awarded him an honorary doctor of arts degree.
Winston was first recorded by John Fahey for Fahey's Takoma Records. His debut album Ballads and Blues 1972 disappeared without much notice, although it was later reissued on Winston's Dancing Cat Records. In 1979, William Ackerman talked with Winston about recording for Ackerman's new record label, Windham Hill Records. At first, Winston played some guitar pieces he liked and then some of his nighttime music on the piano. These became the basis for the record Autumn, which Ackerman produced. Autumn soon became the best-selling record in the Windham Hill catalog. Both Autumn and the following album Winter into Spring went platinum, signifying million-plus shipment in the United States. The Christmas album December became an even greater success, and it was certified triple platinum for shipment of three million. He has recorded twelve more solo piano albums. He is one of the best known performers playing contemporary instrumental music.
Winston released two albums on the music of Vince Guaraldi. He has been interested in Guaraldi's music since he was sixteen when the animated TV special A Charlie Brown Christmas premiered in 1965, and he bought the soundtrack album the next day featuring the music of Vince Guaraldi. He would also watch each new Peanuts special to hear Guaraldi's newest music. In 1996, Winston released Linus and Lucy – The Music of Vince Guaraldi, primarily devoted to the theme music Guaraldi wrote for the Peanuts cartoons: fifteen television specials and one feature film, ranging from 1965 until Guaraldi’s death in 1976. "I love his melodies and his chord progressions," Winston said of Guaraldi. "He has a really personal way of doing voicings." Winston recorded a follow-up album, Love Will Come – The Music of Vince Guaraldi, Volume 2, released in February 2010.
Winston's 2002 album Night Divides the Day – The Music of the Doors consists of solo piano renditions of music by the rock band The Doors. The title of the album is a lyric from their song "Break on Through (To the Other Side)".
In addition to his piano work, Winston plays solo harmonica (mainly Appalachian fiddle tunes and ballads) and solo acoustic guitar (mainly Appalachian fiddle tunes and Hawaiian slack-key guitar pieces). Both his harmonica and guitar playing can be heard on his benefit album Remembrance - A Memorial Benefit, which was released shortly after the September 11, 2001 attacks. In 2006, he recorded another benefit album, Gulf Coast Blues & Impressions: A Hurricane Relief Benefit, followed by Gulf Coast Blues & Impressions 2: A Louisiana Wetlands Benefit in 2012.
Winston also produces recordings of Hawaiian slack-key guitarists for his own record label, Dancing Cat Records, including artists Keola Beamer, Sonny Chillingworth, Leonard Kwan, Dennis Kamakahi, Ray Kane, Cyril Pahinui, Bla Pahinui, Martin Pahinui, Ledward Kaapana, Georg Kuo, Ozzie Kotani, George Kahumoku, Jr., Moses Kahumoku, Cinty Combs, and others. He is also working on recording the American traditional musicians Sam Hinton, Rick Epping, and Curt Bouterse.
Winston suffered from a number of illness, and while recuperating from that last bout of cancer, Winston played the piano in the medical center auditorium, creating 21 pieces, that he says were "kind of circular" and "minimalist." In 2014, he included three of the pieces in a Spring Carousel EP, and a 15-track album, called Spring Carousel - A Cancer Research Benefit released on March 31. Proceeds benefit City of Hope Hospital near Los Angeles, where he was treated and subsequently composed the musical work.
All of Winston's albums are now available on his own Dancing Cat Records, with the exception of the last three releases, which came out on RCA Records.
Many of Winston’s melodic pieces are self-described as "rural folk piano" or "folk piano", a style he developed in 1971 to complement the uptempo Stride piano he had been inspired to play by Fats Waller’s recordings from the 1920s and 1930s. These melodic pieces evoke the essence of a season and reflect natural landscapes. The third style he plays is New Orleans R&B piano, influenced mainly by James Booker, Professor Longhair, Henry Butler, as well as Dr. John and Jon Cleary.
Winston dresses unassumingly for his shows, playing in stocking feet, stating that it quiets his "hard beat pounding" left foot. For years, the balding, bearded Winston would walk out on stage in a flannel shirt and jeans, and the audience would think he was a technician, coming to tune the 9-foot New York Steinways that are his piano of choice. According to the Austin American Statesman in 2015: "As for his piano playing, Winston remains a master of both tone and invention. Starting with a bluesy tune inspired by Professor Longhair — Winston’s most recent albums have included two Gulf Coast-inspired collections — he proceeded through seasonal favorites "Rain" (from 1982's Winter Into Spring) and "Woods" (from 1980’s Autumn). On the latter, he created remarkable 'hollowed' sounds to some notes by reaching inside the piano and muting strings with one hand while striking keys with the other."
On April 19, 2010, he appeared as the sole guest on show 575 of the multimedia WoodSongs Old-Time Radio Hour. Twenty minutes into the program, he describes an unusual method of playing the piano muting the strings, a development inspired by watching blues guitar players. He can be seen reaching into the piano with his left hand and muting the strings, while with his right hand he is playing "An African in the Americas".
Winston resides in Santa Cruz, California.
Winston has survived several serious illnesses, including thyroid cancer, skin cancer, and myelodysplastic syndrome, the latter of which was resolved subsequent to a bone marrow transplant in 2013.2013 Harmonica Solos
2001 Remembrance - A Memorial Benefit (piano, guitar & harmonica solos)
2013 Silent Night - A Benefit Single for Feeding America
2015 Spring Carousel - A Cancer Research Benefit EP
2017 Spring Carousel - A Cancer Research Benefit
1984 The Velveteen Rabbit (solo piano soundtrack with narration by Meryl Streep)
1988 This is America Charlie Brown—The Birth of the Constitution (piano & harpsichord solos)
1995 Sadako and the Thousand Paper Cranes (solo guitar soundtrack with narration by Liv Ullmann)
2002 Pumpkin Circle (solo piano, guitar and harmonica soundtrack with narration by Danny Glover)
2003 Bread Comes to Life (solo piano, guitar and harmonica soundtrack with narration by Lily Tomlin)