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Michael O'Brien

Executive Chef/Owner

Chef Michael O’Brien has had a passion for cooking even as early as 8 years old when he baked a cake for his mother in a meatloaf pan and progressed to cooking for her renown dinner parties. He was never far from his Italian born Grandmother Isabella, where you could find them making ravioli together from scratch in her kitchen. Naturally, Chef found himself working his teens and early twenties in restaurants, and at 24, a Chef friend needed a Sauté Cook at First and Last Tavern in Hartford, CT.  It was there his fire was ignited. His precision and hunger for the craft landed him Sous-Chef in 6 months, and Head Chef the following year; Mike was hooked for life. Craving a solid foundation and a honed skillset, Chef Michael O’Brien enrolled in the Center for Culinary Arts where he graduated with honors. With newly acquired skills, he worked at a few more CT restaurants before venturing out.

He moved to CO where he worked at Hearthstone in Breckenridge, where again he worked his way up to Executive Chef. There, he would cook for a demanding international clientele including running into his largest guest – a 7 ft, 300 lb. black bear on the front dining porch! It was then he learned other cuisines and skills, including, real Mexican from some of his Oxanacan and central Mexican staff, cooking game, working with artisanal cheese makers, exquisite western slope produce, and bear-proofing coolers/trash bins! Chef Michael gained experience at a few more Colorado Rocky locations, such as Vail, Frisco, and the Grand Lake Lodge in Grand Lake, where, as Executive Chef, he led an international staff of 30, cooking for hundreds of people a day, and several weddings every weekend, and in Denver, at Southern Hospitality, which was given the five-diamond award during his time there.

Turning one his dreams into reality, he secured a visa to work in Dublin, Ireland, cooking at the prestigious Residence Club on Stevens Green. He immersed himself in European cuisine and culture for the next year and a half.

Still thirsting for more knowledge, Chef Michael moved back to the states working for a café and catering company in downtown Boston, MA. He then procured a Sous Chef job at Russell House Tavern in Cambridge, in Harvard Square, helping lead a staff of 50+, cooking for 1000 people a day.

Looking for a break from city life, Chef Michael’s journey brought him to Cape Cod. He became Chef of several popular spots, and it was here his big dream of owning his own restaurant started to take shape. Knowing he needed everything he had learned, his passion, well-honed skillset, experience, the fire that ignited inside him every time he carefully crafted and perfectly executed a dish, his love for the art, and the pure exhilaration he experienced as he fed excellent food to guests, brought him to the only logical next step - - - owning his own restaurant.

The dream and desire for a seasonal restaurant in a busy tourist location 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.

This is Michael’s 5th season in 2024, and Chesca’s 30th year in operation. Chef is grateful for his family, friends, dedicated staff, and loyal customers. He’s ecstatic to serve you some of his new and upcoming delectable dishes and looks forward to serving the Island for years to come.