Martha’s Vineyard singer-songwriter and fingerstyle guitarist Tristan Israel introduces his latest album, Out Into the Midnight, with a CD release concert at the Old Whaling Church Saturday starting at 7 p.m.

The first 50 audience members to arrive will receive a free copy of Out Into the Midnight, which Mr. Israel reckoned is about his fifth album in a long and diverse career.

“I’ve done everything,” he said.

Raised in the suburbs of New York city, Mr. Israel first began visiting the Vineyard in the 1960s and started a landscaping business here in the late 1970s. He was a Tisbury selectman for 25 years before stepping down last spring, and he also served for years as a Dukes County commissioner.

In the early 1970s, he played in a band with his older brother Ron, performing as the Pencil Tappers at the Idler and other Cambridge folk clubs.

“We had a cult following,” said Mr. Israel, who drove cabs by day to support his music habit.

“I liked to tell people I was in urban transportation,” he recalled.

The brothers also hitchhiked to the Vineyard, as Mr. Israel recalls in the new CD’s lively lead track Vineyard Reds.

“That’s a song that’s evolved over many years,” he said. “I lived [seasonally] in the late 60s near where the blinker light used to be. It’s a song about those days and about when I used to not live here all the time—the anticipation, hitchhiking here from New York or Connecticut.”

Other songs inspired by Mr. Israel’s freewheeling early summers on the Vineyard and other adventures of his youth include the folksy WMVY Porch Song and the ardent Charlotte in My Dreams, a driving song from the perspective of a lovestruck 21-year-old who’s “listening to the rhythm of the wipers sliding on that glass” as he heads along the highway to his sweetheart.

A mature artist who has never lost his youthful sense of wonder, Mr. Israel aims his songwriting lens at subjects as mundane as a wood louse (The Pill Bug Song) and as cosmic as particle physics (Higgs Boson Ditty, which as a bonus makes reference to the chorus of The Eddystone Light).

“I’m awed by nature, big and small,” he said.

Out Into the Midnight also includes the touching and intimate Father, in which Mr. Israel pays tribute to members of his family who have passed away and notes how they live on in him.

The CD was produced and recorded by Paul Thurlow, a longtime musical partner of Mr. Israel’s who plays many of the instruments and sings backup. Violinist Nancy Jephcote joins them on the CD and at Friday’s concert, where Wes Nagy and Brian Weiland will also perform.

Mark Lovewell opens the show, which includes an intermission with refreshments and a signing by Mr. Israel’s wife, Janet Messineo, of her new book Casting Into the Light.