The Sailing Cow

Before heading to The Sailing Cow in Dennisport, I plugged the restaurant’s address into my GPS and discovered it was on the water. In fact, my GPS made it look like The Sailing Cow was in the ocean. I began to envision an evening of seafood, fresh salt air, and views of Nantucket Sound.

Storm clouds gathered as I left my house, and I knew my chances of enjoying some fresh air were quickly diminishing. Driving along the winding back roads of Dennisport, I finally came to The Sailing Cow, just across from a small beach, surrounded by quaint summer cottages.

The restaurant’s peculiar name stems from co-owner Sandy Jessup’s upbringing on a dairy farm in New York (Robin Thibodeau is also a co-owner). Sandy combined her roots with the maritime inspiration of her new home and found a name that has stuck ever since. This dairy cow theme runs throughout the restaurant, seen in the whimsical cow memorabilia brought back by returning diners as the different types of eggs benedict, each named after a type of dairy cow.


I scored a table right up against the front windows to watch the storm clouds crossing the water, and perused the menu. Born and raised on Cape Cod, I’ve already had my fair share of fried clams. So I was pleasantly surprised to discover Alaskan King Crabs Legs ($11.95) listed as both an appetizer and entreé. The dish—juicy legs dipped in drawn butter and sprinkled with lemon juice—proved as delicious as it is uncommon.

As thunder and lightening rolled through, we were served Jerome’s Jamaican Grilled Lobster (market price), a stand out on the menu. Chopped in half, marinated in a special jerk sauce, and placed on the grill, this unconventional take on many visitors’ favorite crustacean results in a succulent, spicy main course.


For those who shy away from seafood, there are plenty of other choices, from the Flame Thrower Burger ($8.95) to the Billy Goat Salad ($16.95). Kids can find staples like chicken fingers, or a hot dog to keep their hunger at bay.

Another draw of The Sailing Cow is the large drink selection offered at the bar. Frozen drinks and margaritas provide a tropical escape, while those in search of simpler refreshment can find a full selection of wine and beer. The bar serves a special pub menu after 10 p.m., perfect for late night drinks and appetizers.

Our dessert—warm peach pie from the famous Centerville Pie Company—came just in time as the sun began to peek through the storm clouds. Both were the perfect ending to a great meal.

The Sailing Cow opens for breakfast at 7 a.m. (If you’re up for the ultimate challenge, try the Cowabunga Omelette, a 20-egg behemoth.) Lunch offers lighter fare, like salads and sandwiches as well as a long list of specialty burgers. Full catering services, offering Alaskan King Crab Leg or Lobster Bakes, are also available.

–– Fiona O’Connor

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