- In the summer, Castle Island fills with runners, cyclists, dog walkers, fishers, strollers, and Bostonians of all ages. An outdoor gathering place, Castle Island hosts a historic fort that sits atop a green hill. From it, watch the boats pass through the harbor, airplanes take off from Logan, children play on the swings, and brave souls take a dip in the chilly shore. One of Boston's most revered greasy spoons, Sullivan's is a take-out food joint onsite that serves burgers, fries and ice cream.
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