Tom Rush was a teenager with a new driver’s license when he first set foot on Martha’s Vineyard in the late 1950s.

His Aunt Sarah lived in West Tisbury and offered to let him spend summers on the Island. After one summer, Mr. Rush was curious to know what the Vineyard had to offer in the winter.

Back then, only the Lampost in Oak Bluffs was open, he recalled in a recent phone call with the Gazette, in advance of his upcoming concert here. As part of his self-proclaimed 67th Annual Farewell Tour, he will play at the Strand Theatre in Oak Bluffs on May 23.

His first winter on the Island was a quiet one. Even his experience at the Lampost was unique, he said, the clientele being mostly fishermen’s wives who had nothing else to do while their husbands were all out on their boats.

There was absolutely nothing going on, he said. Eventually he headed off to college, where he began a successful folk singing career that is still going strong more than 60 years later.

“I graduated with an English Lit degree,” he said of his time at Harvard, where he graduated from in 1963. “And nobody was lining up to pay me to read books, but I was getting paid a little bit to get on stage and make music, so I figured, well, I’ll do this until I figure out what I want to do when I grow up. I’m still trying to figure out what I want to do when I grow up.”

In 2024, Mr. Rush released his 19th album titled Gardens Old, Flowers New, which he feels is his best. The album encapsulates a lifetime of experience recording and performing.

Mr. Rush said what he likes most about his chosen profession is exploring the nature of the audience. Much like his instruments, Mr. Rush enjoys getting the audience in tune with the music.

“[The audience] is, of course, half the equation,” he said. “I’m half and they’re the other half. It’s always an adventure to see what’s going to happen next.”

“The audience doesn’t want perfection,” he continued. “They want connection. And that’s good news, because I’ve never been any good at perfection, but I think I’ve gotten better at the connection part.”

Mr. Rush will be accompanied by Brendan Cleary when he performs at the Strand Theatre in Oak Bluffs on May 23. Tickets are available at circuitarts.org/tomrush