Chesca's Restaurant

Chef Michael O’Brien has had a passion for cooking as early as 8 years old when he baked a cake for his mom in a meatloaf pan and then cooked for her renown dinner parties. He also loved making ravioli with his Italian born Grandma Isabella. Early on, Chef worked in and out restaurants in CT and FL, and at 24, a Chef friend of his needed a Sauté Cook at First & Last Tavern in Hartford, CT. It was there his fire was ignited. His hunger and passion landed him Sous-Chef in 6 months, and then Head Chef, he was hooked for life. Craving a need to learn, Chef enrolled at the Center for Culinary Arts where he graduated with honors. With his new skills, he worked at a few more CT spots before moving on.

Chef moved to CO where he worked at Hearthstone in Breckenridge, where again he worked his way up to Executive Chef. Michael worked in a few more CO towns, such as Vail, Frisco, and Grand Lake at the Grand Lake Lodge, as Executive Chef. Then to Denver, at Southern Hospitality as Executive Chef, which was given the five-diamond award during his tenure there.

Turning one of his dreams into reality, Chef secured a visa to work in Dublin, Ireland, cooking at the prestigious Residence Club.

Chef moved back to the states, working at a café and catering company in Boston, MA. He then landed a Sous-Chef job at Russell House Tavern in Cambridge, MA 

Chef Michael’s journey took him to Cape Cod. He worked as Head Chef at several popular spots, and it was here his big dream of owning his own restaurant started to take shape. 

The dream was finally realized when he stumbled upon Chesca’s in Edgartown, MA, it was love at first sight and he knew this was it. In 2020, in the middle of a pandemic, Chef’s big dream came true. Michael O’Brien became Chef Owner of Chesca’s Restaurant.

2024 is Michael’s 5th season, and Chesca’s 30th year in operation. Chef is grateful for his family, friends, dedicated staff, and loyal customers.  Chef looks forward to serving the Island for years to come.




Return to Chef Lineup