Jon Gailmor: Vermont’s Musical Icon Returns To Westport Roots

Forty years ago, Jon Gailmor sang: “My reason for being is music.”

It still is.

And — half a century after he left Westport for Vermont, where he crafted a life as a beloved singer/songwriter, radio show host, children and adults’ workshop leader (and who represented the state at the Kennedy Center’s 25th Anniversary Celebration) (and wrote a campaign song for Burlington mayoral candidate Bernie Sanders) — he’s returning home.

On Sunday, November 5 (12:30 p.m., VFW Joseph J. Clinton Post 399), Gailmor headlines Suzanne Sheridan’s “First Folk Sunday.”

if you remember him from his days here, you know what a treat that is.

If you have never heard him — or of him — you’re in for a treat.

Jon Gailmor

Westport played a huge role in Gailmor’s life, yet it was not the only influence. His grandfather and father were Orthodox rabbis. But Gailmor’s father, William S., left the synagogue to become a journalist and radio host, interviewing “lefties” like Paul Robeson and Fredric March. He was a major fundraiser for Henry Wallace, during his 1948 Progressive Party campaign for president.

The Gailmors moved to Westport when Jon was in 9th grade. After a stifling junior high experience in Philadelphia, Bedford was a “godsend.” The atmosphere was nurturing; principal Norm Flint treated students “with dignity, like real people.”

Staples High School proved equally enriching.

George Weigle’s choral program provided both a home and a launching pad. Gailmor appreciated the legendary music director’s talent, passion and great humor.

Some of his fondest moments were on the Staples stage. Some of his closest friends to this day are fellow Orphenians like Roger Kaufman and Steve Emmett.

Staples choral teacher George Weigle had a great influence on Jon Gailmor. (Photo courtesy of Ken Lahn)

Gailmor found more musical mentors at the University of Pennsylvania, where he sang in an 80-man glee club, and traveled to South America. “That all it takes,” he notes. “Someone to turn the light on, and shape your life.”

But it took just one semester at Temple University’s graduate school of education for Gailmor tor realize that he was not cut out to be a teacher.

“I’m not wired to be in the same place every day,” he says. “And it’s ludicrous to think you can learn how to teach by taking courses. You have to be in front of kids. They teach you.”

He spent several months hitchhiking around Europe, and singing in cafés.

Back in the US, he began a solo career. He bombed at his very first gig — literally. A bomb scare evacuated Mark’s Place, the second-floor Main Street club.

He wasn’t ready to be on his own. He moved to Providence, where Brown University graduate and former Staples classmate Rob Carlson was ready to move from rock ‘n’ roll to a softer sound.

As a duo playing college coffeehouses, Carlson & Gailmor earned a devoted following throughout the Northeast.

They caught the eye (and ear) of John Franklin, a Westporter with music industry connections. He brought them to Polydor Records.

The pair recorded an album, of mostly Carlson’s compositions. The label then went to work, adding “beautiful instrumentation,” Gailmor says.

In the process though, “they over-produced it.”

Then, Polydor failed to promote it. “Peaceable Kingdom” —  named for the wistful tune about Quaker preacher Edward Hicks’ paintings depicting all manner of animals lying down together — never gained the notice it deserved.

(It remains one of my favorite albums of all time. Plenty of others who heard it, and remember it fondly, agree.)

The experience taught Gailmor that he didn’t want to be “in the big time.” It was a freeing moment. “I’ll never have to wonder ‘what if’ again,” he says.

The pair split up. Decades later, they appreciate each other’s talents and musicianship. Carlson — who still lives and performs locally, after a career that included running an independent record company, and recording parodies of singers and news events — will join Gailmor for a few songs at “First Folk Sunday. (Suzanne Sheridan will do the same.)

Jon Gailmor (left) and Rob Carlson played together in 2018 at the Weston Grange.

Vermont — with its welcoming people, beauty and vibe — beckoned.

“It’s so different from any place on earth,” Gailmor says. “It’s so nurturing, for people with passion.”

Gailmor returns the love. “Long Ago Lady” — a paean to the state, including the line “My reason for being is music” — captures its uniqueness perfectly.

In the Green Mountain State, Gailmor performed in bars and similar venues. He did a few “Live at the Depot” radio shows (from an old railroad station), then decided to try one for kids.

An instant success, it evolved into “Just Kidding,” a weekly unscripted story and song show. It ran for 25 years.

Gailmor — the man who did not think he was cut out to be a teacher — has also spent decades in schools, running songwriting workshops for children.

“It’s phenomenal what they have inside them,” he says. He helps them translate their words and music into songs, which they then perform.

Gailmor roams all over the state, from his home in Elmore. (The town, he notes proudly, is the site of Vermont’s last one-room schoolhouse.)

His home grew emptier in January 2022, when his wife Cathy died of ALS. Music helps, he says, on his long journey through grief.

Music remains Gailmor’s “reason for being.” And it’s the reason he returns next month, to the town that helped make him who he is.

“It will be sublime. But I have no idea if anyone will come,” he says.

For once, he’s dead wrong. On November 5, Jon Gailmor will whistle a very different tune.

(Click here to learn more about Jon Gailmor. Click here for tickets to his First Folk Sunday show. Questions? Email info@firstfolksunday.com, or call 203-222-1441.)