Jesse Winchester: Musician whose tender, wistful evocations of the American South he was forced to leave won him a loyal following

When he boarded a flight from Memphis to Montreal in 1966, carrying only $300, a guitar and a ripped-up draft notice to fight in Vietnam, Jesse Winchester would scarcely have believed that the moment would come to define him in the public eye, despite the long and illustrious career as a singer-songwriter that followed.

Winchester fled to Canada to evade the call-up on grounds of personal conscience. The label of draft dodger, or resister, depending on how one viewed the war in south-east Asia, never went away and he frequently described himself, tongue only in cheek, as "not popular". But if he was seldom lauded in the way contemporaries such as James Taylor were, and remained more a cult figure than a commercial proposition, there was no shortage of artists ready to take his material into the US singles and country charts.

His songs, particularly during his exile, were often tender, melodic evocations of the South in which he was born and raised, loved and left. "The Brand New Tennessee Waltz", for instance, was both a song of unfulfilled love and a wistful eulogy to his family's home state; a seamless fusion of the personal and the political. "I left Tennessee in a hurry, dear," he sang, "the same way that I'm leaving you." Winchester's version, which appeared on his eponymous debut album of 1970, showcased his trademark economy of phrasing and the gentle, sensitive but rich and warm voice, although his enduring southern drawl was more evident on other tracks.

Among those who recorded the song were Joan Baez, the Everly Brothers, the Walker Brothers, Lyle Lovett, Ronnie Hawkins and Matthews Southern Comfort. Few came close to capturing the sense of regret and longing Winchester conveyed. From the same album, and also concerning displacement, "Biloxi" was a hymn to the beachside city on the Mississippi Sound. "The stars can see Biloxi, stars can find their faces in the sea," he crooned, the inference being that the separation from family and friends – which he assumed would not end during his lifetime – meant he would not see Biloxi again. The country singer Jimmy Buffett brought the song to a wider audience.

For all that the haunting, homesick character of Winchester's early output centred on neighbouring states – "Mississippi, You're On My Mind" was a shimmering, almost spiritual example from 1975's Learn To Love It – Winchester was born in Louisiana. He came from "a long line of lawyers and preachers"; his great-grandfather had been Episcopal Bishop of Arkansas. Later calling himself "a feeble follower of Jesus", he attended a high school run by the Christian Brothers.

His college studies led him from Memphis to Williamstown, Massachusetts, where he majored in German. On receiving his draft notice with his diploma in 1966, he decided he could not fight in Vietnam. Four decades later, after Buffett introduced him as "my personal hero" at a benefit concert in Alabama, Winchester said he was "certainly no hero ... I just don't believe in war. I'm proud of my dad for fighting in the Second World War, but I needed to really believe before I took up a gun."

"Young, impulsive and righteous", he arrived in Quebec where he married and raised a family. Despite joining a group, Les Astronautes, he found his vocation performing solo in cafes and restaurants. Robbie Robertson of The Band championed him and produced Jesse Winchester, to which Levon Helm also contributed. The follow-up in 1972, Third Down, 110 To Go, took its title from American Football and was co-produced by Todd Rundgren. Revealing a wry humour alongside the sadness, it reached No 34 in the Canadian chart but only 193 in the US.

Indeed, the dual citizen's highest album-chart placing in his home country remains 115 for 1977's Nothing but a Breeze, whose title song contained the exquisite line: "I want to live with my feet in Dixie and my head in the cool blue North." The publicity generated by President Carter's amnesty for draft resisters that year possibly accounted for its relative success, along with Baez's dedication to him of the song "Please Come To Boston" when Bob Dylan's Rolling Thunder tour played Toronto.

On his return to live shows in the US, Rolling Stone declared him "the greatest voice of the decade". In 1981 he flirted with pop-star status, "Say What" hitting No 32 in the singles chart, but stayed in Canada until 2002 when a new relationship, with a Memphis woman called Cindy who became his third wife, prompted a homecoming to Charlottesville, Virginia.

His main source of income lay in the royalties from covers such as Reba McEntire's "You Remember Me", Wynonna Judd's "Let's Make a Baby King", The Mavericks' "Oh What A Thrill" and "My Songbird" by Emmylou Harris. Winchester continued to make albums, his 10th and final studio set being Love Filling Station in 2009, when his rendition of "Sham-A-Ling-Dong-Ding" on Elvis Costello's Spectacle show rendered the host speechless and reduced a fellow guest to tears. In 2011 Winchester was diagnosed with cancer of the oesophagus. After treatment he resumed touring – he was as entertaining and amusing as he was powerful and dignified on stage – but the respite proved brief.

James Ridout (Jesse) Winchester, singer, songwriter and guitarist: born Bossier City, Louisiana 17 May 1944; died Charlottesville, Virginia 11 April 2014.