His songs were recorded by many notable artists, including Patti Page, Elvis Costello, Jimmy Buffett, Joan Baez, Jerry Garcia, Anne Murray, The Weather Girls, Reba McEntire, the Everly Brothers, Lyle Lovett, Emmylou Harris, George Strait, Gary Allan, Willie Nelson, Jennifer Warnes, The Mavericks, Jerry Jeff Walker and Michael Stanley.

[4] Winchester was born at Barksdale Army Air Field, near Bossier City, Louisiana, United States, and raised in northern Mississippi through age 12, when his family relocated to Memphis, Tennessee.

He graduated from Christian Brothers High School in Memphis in 1962 as a merit finalist, a National Honor Society member and the salutatorian of his class.

Under the auspices of the Band's Robbie Robertson, another Canadian, Winchester began his recording career in 1970 with a self-titled album released on the Ampex label.

[8] "Winchester's first LP was apolitical on the surface and not without its conservative tendencies, but its brooding lyricism and barely contained ferment reflected the force of will it took for him to flee this country."

Because of his status as a draft-evader, entailing that he was subject to arrest had he entered the country, he was unable to tour in the United States, and he became recognized primarily as a songwriter.

His best-known songs include "Yankee Lady", "The Brand New Tennessee Waltz", "Mississippi, You're on My Mind", "A Showman's Life","Biloxi", "That's a Touch I Like", and "Every Word You Say".

"I'm Gonna Miss You, Girl", written by Winchester, was recorded by American country music artist Michael Martin Murphey and released in October 1987, as the lead single from the album River of Time.

[14] Winchester continued to record and perform throughout the United States and Canada, releasing his tenth studio album, Love Filling Station, in 2009.

[16] Quiet About It, a tribute record to Winchester, was released in 2012, featuring James Taylor, Lyle Lovett, Lucinda Williams, Rosanne Cash and Jimmy Buffett, who spearheaded the project, among others.

Rolling Stone called it "a gentle collection of playful songs about love, memory and gratitude that amounts to one of the most moving, triumphant albums of Winchester's 45 year career.