Dilly’s Taqueria opened for business on Circuit avenue in Oak Bluffs three summers ago. It was located in the building that once housed Skinny’s Fat Sandwiches.

This summer Dilly’s is operating out of the Ritz Cafe.

Dilly’s is named for owner Adam Rebello’s three-year-old daughter Dylan. He also has a one-year-old son named Cole. His wife Guinevere completes their family operation running Dilly’s advertising, social media and marketing. She helps out in the kitchen as well.

Mr. Rebello was born on Martha’s Vineyard and graduated from the regional high school in 2008. After high school, he moved to Florida where he worked at a golf course before returning to the Island full time. He found jobs as a bartender at the Island House and at Farm Neck Cafe. Those experiences piqued his interest in the restaurant business, he said.

“I think what keeps me in this business is the people,” he said. “I love people.”

He also looks to his parents, Todd and Mia Rebello, as inspirations.

“Having my parents set the example as business owners really inspired me, it drove me to grow up to be that,” he said. “It was something I expected of myself. That comes from my parents and grandparents.”

His grandparents, Marilyn and Anthony (Tubby) Rebello, were longtime owners and operators of Anthony’s Restaurant in Oak Bluffs.

When Mr. Rebello first opened Dilly’s he also worked as a manager at Coop De Ville on the Oak Bluffs Harbor.

“The biggest thing about being a manager was making sure you showed up and you did what you had to do. As an owner, you have to worry about everyone else. You have to make sure they’re okay and they can do their job. There’s so much more.”

Mr. Rebello said he is incredibly grateful for his staff; many who have been with him since opening day.

“I’ve played sports my whole life and the way I’ve always thought of running a restaurant was as a team,” he said.

Still, even with a great staff, starting a business is hard, Mr. Rebello admitted.

“Those first couple years, imagine working 60 to 70 hours a week trying to build a business and then at the end of the year there’s nothing left. The money you invested, there might be a couple thousand dollars and then you get a tax bill. That’s tough, to work that hard and then come out and hope you can open next year.”

Failure was never an option, though, not when the rent was raised or the pandemic hit. The chance to work with Larkin Stallings, owner of the Ritz, was one of the main reasons Mr. Rebello pursued a partnership with the downtown bar that has been a staple of Oak Bluffs for decades.

“You don’t get many opportunities to work with someone like [Mr. Stallings] who has been in the business for a very long time, who is a stable presence you can talk to and is very open and transparent about what’s going on,” Mr. Rebello said.

Mr. Rebello said he feels his journey hits home for many Island kids.

“When you graduate you want to leave, you want to get out, you want to go see the world and see if you can make it out there. But as I got older I wanted to be back, I wanted to build a legacy for my family. It’s already been built for me by my parents and by their parents before them. I want to continue that, I want my kids to see how hard I work and then want to do that.”