Larkin Stallings, owner of the Ritz Cafe in Oak Bluffs, realized his prospects of becoming a famous bass guitarist were grim shortly after opening his first music club. It was 1976 and he was 19 years old.

“I was playing a gig with a really great funk band and realized that I was never going to be good enough to make any money,” Mr. Stallings said recently over a cup of coffee at the Ritz. “In a desire not to be poor, I had already opened this little spot down in Palo Alto. It was just a kind of a natural move and something I was better at than I was as a musician.”

His life’s work has been in bars and clubs ever since. His first club was called My Oh My, and it sat at the intersection of Homer avenue and High street in Palo Alto, Calif. Later he studied hotel and restaurant management at the University of Houston, and then opened three bars in the Houston area.

He bought the Ritz in 2014.

But for a long time the Vineyard was not on his radar, as he and his wife Jacqueline were raising their four kids in Houston. In fact, he had never heard of the Island when Jacqueline brought it up, back in the 1990s, even though she had never visited either. And yet she told him they would move there one day. Her family was enamored with the Kennedy family (she is named after Jacqueline Onassis Kennedy) and she became intrigued after reading about Ms. Kennedy-Onassis’s Vineyard compound.

“I said, if you want vineyards we’ll go back to Napa in Northern California, where I’m from,” Mr. Stallings recalled.

Mr. Stallings has kept the bar's gritty character and given it a touch of southern hospitality.

Ray Ewing

Mr. Stallings has kept the bar's gritty character and given it a touch of southern hospitality.

Ray Ewing

The couple visited the Island for the first time in the winter of 1997. It was raining and nothing was open. They fell in love with it.

“It’s one of our favorite times to be out here, when pretty much nobody is here but us,” he said. “We’ve been in love with the Island for a long time. The first time we came here it just fit like a glove.”

The Island’s natural beauty made the couple fall in love initially, he said, but they stayed because of the people.

“We made friends very quickly out here. My closest friends are from the Vineyard,” he said. “It’s a weird nexus. The type of people you meet out here [are] from all walks of life.”

The Stallings bought a home on the Island in 2006 and moved here full time in 2012. Two years later Mr. Stallings purchased the Ritz from longtime owner Janet King. He had been walking down Circuit avenue when he saw a “for sale” sign in the window. On a whim he made a deal with Ms. King, but it would be another four months until he took ownership of the bar, which he blamed on lawyers messing things up.

In hindsight he sees the delay as a blessing. He took over in June of 2014, just before the start of the busy summer season, which meant he didn’t have time to change the bar’s gritty charm, he said.

“What I needed to do was take it as the Ritz, just period, no changes, and run it for a season and figure out what it is that the Ritz really meant,” he said. “I could have screwed it up. I could have come up with my own ideas and changed it or messed it up. I didn’t have time to mess it up.”

He looks back on that first year as an educational period, he said.

“I got a deep dive and a deep education to what the Ritz was, is, could be and more about Oak Bluffs, how that works and where the Ritz fits into that whole fabric,” Mr. Stallings said.

Live music has always been a staple of the Ritz, which is the best part about owning it, he said.

“To be able to sit in a room this small and hear that caliber music right up next to you, there’s something magical about it,” he said.

Mr. Stallings has kept the bar’s hole-in-the-wall character but added a touch of southern hospitality, he said.

“We really want this place to be for whoever you are, wherever you come from,” he said. “You can walk in and feel like, ‘yeah, this feels comfortable, I’m wanted here,’ and I think that’s super important.”

Mr. Stallings continues to manage his Houston bars as well as becoming a fixture in the Island business and service communities. He is the president of the Oak Bluffs Association—the town’s business coalition—and vice president of the board of Martha’s Vineyard Community Services. He also serves on the board of Vineyard House, the Island’s sober living center located in Vineyard Haven.

He said his involvement in the various nonprofit organizations as well as the Ritz has helped him to get to know the Island community in a way he never would have been able to as a seasonal resident.

“I have been accused of being a workaholic, and that’s not true,” he added. “A workaholic is somebody who does all this to avoid something else. I do all this because it’s freaking fun and it’s very fulfilling.”