A deep path leads through the snow to Mike Benjamin’s front door, where Bella, a golden retriever, greets you with a wet tennis ball. Parts of the house are 150 years old, and glass milk bottles still lie buried around the Edgartown property, the site of the former Martha’s Vineyard Co-op Dairy. The dairy dates to the 1940s when there were a number of thriving dairy farms on the Island that supplied residents with milk. A handmade sign on the road still warns travelers to watch out for cows that have been gone for decades.

“All the way to the ocean was clear-cut pastures with 300 head of cattle,” Mr. Benjamin said, motioning out the window toward Vineyard Sound, beyond some snow-covered pine trees.

Inside the house where it’s warm, Mr. Benjamin gets out a steel guitar, painted green with palm trees, that he bought from Island musician Maynard Silva many years ago. Mr. Benjamin started his musical career playing in Harvard Square and in the subways of Boston. He studied music at Hampshire College and at the New School in Manhattan in the 1980s, but most of what he knows about music he learned onstage.

“I have enough theory to get me by,” he said. “All of that, I learned more on the bandstand than by studying it — what you need to know to get through a gig and to be able to communicate with musicians.”

Holding court at The Ritz. — Mark Lovewell

In the 1980s, Mr. Benjamin was a go-to session musician in New York city, singing for major TV and radio commercials. But when his wife Sandra became pregnant with their daughter Charlotte, now 18, the couple began looking for a getaway. Mr. Benjamin knew the Vineyard from playing gigs here as a teenager in the early 1980s, when he visited during a couple of summers with his high school band. The Ritz Cafe in Oak Bluffs was one of the first Island venues where he performed and remains one of his favorites.

“It was January, so I thought, let’s just go up there for winter,” he said. “We’ll have a kid in a few months, we’ll fix up the house.” The plan was to stay for the summer and then go back to the city, he said. “We just never did that.”

Mr. Benjamin began playing with the Vineyard-based band Entrain, but then started focusing on his own music, forming the Mike Benjamin Band and cutting four solo albums. He is now working on a fifth album, with tracks recorded at his studio in Edgartown, and in Boston.

The band’s repertoire includes hundreds of songs and many genres. Grateful Dread, another project Mr. Benjamin is involved with, plays reggae, ska and other Caribbean-syle arrangements of songs by the Grateful Dead. Weddings are a specialty for the Mike Benjamin Band, which is often booked every weekend from May to October.

“That requires more versatility,” Mr. Benjamin said. “I’m probably doing a wider range of styles at weddings than I’m doing anywhere else, like from Sinatra to Bruno Mars. Just a real mixed bag.”

Explaining the band’s philosophy of covering songs, Mr. Benjamin said they will play nearly any style of music, but each song should be built to last.

Mike Benjamin's musical family is large and extends off-Island. — Mark Lovewell

“There are always songs that are coming out that are contemporary, but they follow the classic form that we’re all used to and even have some of those sounds,” he said. “Adele – some of that stuff sounds like it could have been recorded in 1950.”

Nestled in the yard, near a wooden chicken coop, is the studio where Mr. Benjamin and his band rehearse and record. An old, snow-covered Hammond organ sits on the porch with some other furniture, as if quietly observing the snow and listening to the muffled cooing of chickens.

Inside the studio are guitars, a stack of recording equipment with blinking lights, some memorabilia from past projects, and a small bunk bed for visiting musicians.

The band’s several configurations throughout the year might include a five-piece horn section, an electric quartet for summer parties or an acoustic trio. Mr. Benjamin’s musical family is large and extends off-Island.

An acoustic band, playing Tuesdays at the Ritz this winter, includes Paul Size on guitar, Wes Nagy on accordion and Steve Tully on flute, saxophone and clarinet.

“Some people have an open invite,” Mr. Benjamin said. “It’s basically like if you’re here and I’m playing you’re welcome to be on the gig. And tunes will change accordingly.”