Few people embody the statement “still waters run deep” more than Island singer-songwriter Willy Mason, equal parts thoughtful and lighthearted as he considers his musical roots and his career.

He is half done with his next album, which should be released around January. In August and September, he will be playing festivals in the United Kingdom.

“It’s like getting to be the band at a big party,” he says, having appeared before mass audiences at Glastonbury and similar festivals before. He also has toured with major acts in the music business, such as Radiohead and Norah Jones, releasing several albums of his own along the way, including his well-received debut, Where the Humans Eat.

But for now he is not busy driving the small schoolbus he purchased to use as a tour bus; more often, it’s being used as his own personal Saferides program for friends. He’s got a gig on Tuesday at the Old Whaling Church to benefit affordable housing, and another benefit coming up for Hospice of Martha’s Vineyard. But in the meantime Mr. Mason and his cat, Striper, are hanging out on his West Tisbury porch and making music. Which is more than fine by him.

“For the most part I enjoy touring,” Mr. Mason says, but it has its challenges.

He compares going on tour to going on a camping trip: “Once you begin your tour, there’s a set of circumstances that you’re stuck with,” and making those circumstances work for you takes some improvisation.

Touring also can bring about homesickness. Mr. Mason feels attached to the Vineyard, where he grew up: “It can be hard to be away for long periods of time. I’m trying to find the right balance, I guess, between being here and being away.

“A lot of the people I collaborate with, most live here. The more that I can be around here sort of feeds the creative process,” Mr. Mason says, before adding that touring can help the creative process, too: “It’s good to keep moving and get a different perspective every now and then. I get some of that from touring.

“[But] sometimes I feel conflicted being on the road. There’s a strong bond between people who call this place home.”

Being a Vineyarder plays into his music. “It’s been a big part of my developing a certain way of seeing things, which is, of course, still evolving,” Mr. Mason says of growing up here.

“There’s a strong culture here and a strong sense of freedom for a young person growing up. It gave me a lot of strength, when I first started traveling off-Island, to believe what I wanted to believe.”

Mr. Mason grew up in a musical family. His mother, father and brother are all musicians. “I was always gonna play music,” he laughs.

“I only succumbed to the fate [of being a professional musician] when I started getting gigs out of high school,” he adds.

When asked if music felt like an occupation or a hobby, Mr. Mason replies, “Right now it’s my occupation. It’s my hobby, too.

“I like playing music with other people as a hobby. It’s nice to think of myself as a songwriter right now.

“I steal a lot of melodies,” Mr. Mason says. “Sometimes I’m conscious of it, sometimes I’m not, but I always try to do right by them. I think that there’s a lot of beautiful melodies that should be kept alive, one way or another.

“I like writing words when I’m walking around,” he says of his songwriting habits. “Then I can sing out loud.

“I tend to write a lot more songs when I don’t have a motor vehicle that’s working or inspected or registered.”

Mr. Mason has been performing music on the Island since adolescence and keeps in touch with former bandmates. “I still play music with a lot of the guys from Keep Thinking, which was my first band here,” he says.

Has the thrill of the amateur been lost in the wake of becoming a professional? Not for Mr. Mason. “I don’t think it’s lost the fun. There’s the thrill of discovery sort of thing, when you’re first starting out and you don’t even know what your own music sounds like, really.”

Mr. Mason gives the impression of being a musical philosopher. Having released a few albums already, with another on the way, he’s more aware of what he calls his “case history.”

“That’s almost like another member in the band that you’ve got to sort of work with — who you have been,” he says.

When Mr. Mason doesn’t perform on his own, he and his brother, Sam, take the stage together. He has been working with Sam to find a way to put on “a really good show with just the two of us.”

His songs come from a personal place. “Most of the things in the world at large that interest me and that affect my life, whether it’s political or financial or cultural, the way that I like to analyze those things is through the effect that they have on a personal level,” Mr. Mason says of his songwriting. “Bringing it back to the most personal level of decision-making based on selfish realities.

“It’s the best way I can think of to understand most of these things I’m trying to figure out why people act the way that they do.”

Mr. Mason’s father, songwriter Mike Mason, briefly interrupts the interview to recount a conversation he’d had the night before with a young man who was eager to practice law on the Vineyard, despite knowing that he would make less money here than he could off-Island. His son feels the same, and his ties to the Island are stronger than his desire for monetary success.

“There’s a strong solidarity throughout the community here, so that people will definitely make sacrifices and do what they can to remain a part of it,” the young musician says. “It feels like it’s something to protect. “


Willy Mason will be performing at Raising the Roof, a concert to benefit the Island Housing Trust and Habitat for Humanity of Martha’s Vineyard on Tuesday, July 5 at the Whaling Church in Edgartown at 7 p.m. Also on the bill is Mackenzie Wasner, a rising country music star, performing as an acoustic duo with her father, Pete Mackenzie a singer/songwriter/keyboardist for Vince Gill. Tickets are $50 general admission, or $100 for patrons to enjoy an artists’ reception and refreshments after the show.