Jon Gailmor. Courtesy photo This story by Aaron Calvin was first published in News Citizen on Dec. 11, 2025. “I’m gonna die with a smile if it kills me,” Jon Gailmor sang on his 1990 song of the same name. He sang it again in a video he released in April 2020, at the height of the  Covid-19 pandemic, in the midst of a project in which he posted a video of a performance each day of the lockdown, like bottled musical messages cast into the digital ocean, beginning with an original song about the virus on March 25, 2020, and ending with Steve Winwood’s “Back in the High Life Again” as the vaccines rolled out on May 9, 2021. As a description for the video where he sang about planning to revel in the pleasures of life so deeply that he would embrace its end satisfied, he appended a note: “My philosophy of life since August 5, 1948.” He sang his song about leaving this world with nothing left undone for the last time on Nov. 30 and died at 77 with a smile on his face in his son’s New Orleans home following a leukemia diagnosis 18 months prior. Gailmor was born in Manhattan and spent his early childhood in Philadelphia at the dawn of postwar America. His father had come from a family of Orthodox rabbis, according to Westport reporter Dan Woog, but his father, William, left the synagogue to become a leftist journalist and eventual speechwriter for Henry Wallace, one-time vice president to Franklin Delano Roosevelt and Progressive Party presidential candidate the year Gailmor was born, he told the Burlington Free Press in 1981. He was Wallace’s godson. The future Vermont music icon graduated from Staples High School in Westford, Connecticut, in 1966, and his early adulthood was shaped by a turbulent world for someone born out of the hope that World War II would be the last war. He remarked to the Free Press that marching in the Poor People’s Campaign to Washington, D.C. in 1968, a protest for economic justice for the poor organized by Martin Luther King, Jr. prior to his assassination but carried out after it, was one of the “most beautiful days of (his) life.” The students at the Elmore School spent a week working with local singer and songwriter Jon Gailmor writing original songs.Photo by Diane Nicholls Despite the core of optimism that would become his hallmark as a professional musician, he grew increasingly pessimistic about the political state of the country as the sixties soured into the seventies. After vagabonding about Europe and releasing a little noticed folk record on British label Polydor with a former high school classmate, he decided trying to cut it in the commercial music industry was not for him. In the late 1970s, he drew closer to Vermont, settling on the shores of Lake Elmore. “Vermont is what America could be and should be. Vermont is a country, a closely-knit country of its own. In many ways, Vermont feels like the ‘60s. There’s that ‘being a part of something’ and ‘having a say in something’ attitude here,” he said. Vermont in turn embraced him and allowed his career as a children’s entertainer, teacher and troubadour to flourish. Gailmor planted his songs like little seeds, one by one, in classrooms and in parks and churches and village granges; in “Just Kidding,” the radio show for children on WDEV that ran for 25 years; in his popular songwriting workshops; and his general ability to break out a song wherever he went. For nearly half a century, Gailmor planted his songs everywhere he went, whether it was a packed crowd in his hometown Elmore United Methodist Church or with the Vermont Symphony Orchestra, which he performed with in the summer of 1993 in a performance that prompted a Free Press writer to dub him “Vermont’s John Denver.” “The guy could play anywhere, anytime and not miss a beat,” Rusty Dewees, fellow entertainer and Elmore resident, and friend of Gailmor’s, said. “He produced the same high-level output whether it was a dementia ward where everyone is sleeping, or a sold-out show with 10,000 people. You don’t see that with all entertainers. It’s unique.” Though he wasn’t afraid to play broadly across genres, his workaday approach to songwriting, as something that could be born from anyone as long as it was a true feeling, feels directly descendent from the populist folk music tradition, not stadium pop country. Writer Tom Mckone quoted a friend in his remembrance of Gailmor in The Barre Montpelier Times Argus as calling him the “Pete Seeger of Vermont.” He was well on his way to gaining that status when he opened for Seeger and Arlo Guthrie at Sugarbush in 1978. In an essay on the songwriting method he passed along to students of all ages published in 2006, Gailmor wrote that, in his misbegotten days trying to make it in the music business, he learned that trying to write a hit left him feeling empty, and that “honest writing unearths threads that connect us all, and that songs that were remembered came “from the gut.” Despite his endless circuit of performing, teaching and raising his family with his wife, Cathy Murphy — she died in 2022 — Gailmor still devoted time to his role as town moderator, which he held through last year. Armed with Robert’s Rules of Order, he ran Town Meeting Day in Elmore for decades, facilitating the kind of community-centered political life that made him choose Vermont in the first place. Gailmor would dote on Murphy whenever he got the opportunity, including in a 2022 interview with the News Citizen about town moderators itching to get back to in-person town meetings. He said one of his favorite photos of his wife was from Town Meeting Day 1980, when she delivered “an eloquent presentation” about the importance of a nuclear arms freeze between the United States and the Soviet Union. Of course, because this love for Town Meeting Day was a true feeling, Gailmor had to write a song about it. “A Town Meeting Tune,” from his 1994 album “Checking In,” is a paean to the annual enactment of small-scale democracy. “Creating songs is exhilarating and fulfilling,” Gailmor wrote in 2006. “It also saves me an awful lot of money on therapy. As I age, my pieces become more personal and carry an urgency for me to launch them into the world while I’m still in it.” Patrick Bilow and Tommy Gardner contributed to this story. Read the story on VTDigger here: Vermont music icon Jon Gailmor departed the way he came in — with a song. ...read more read less