Along the Freedom Trail, you’ll find Union Oyster House, the oldest restaurant in operation in the United States. A testament of reliable Bostonian fare, the Kennedys frequented this old-school joint—Booth 18 is even named the “Kennedy Booth” because it was the late president’s favorite spot for Clam Chowder.
The food is so-so nowadays, but come for the décor that’s reminiscent of a bygone era and stay for the historic charm that the place still exudes today.
Family-owned Rainbow Seafood Restaurant has been serving a fun dining escape to locals and tourists alike since 1984, giving away free boat rides to hungry guests from nearby piers. Their specialties are best enjoyed with company, their portions massive enough for sharing between big groups. Make sure to order signature dishes such as Rainbow Fish Garoupa, Baked Lobster with Butter Sauce, and Spicy Prawns.
If there’s a dish that emerged from Hong Kong’s bygone typhoon shelter culture, it’s the classic spicy crab. Under Bridge is a well-known spot that serves the iconic dish with their own flavorful twist of toasted garlic, shallots, and spring onions. The restaurant also offers other hearty specialties including Sautéed Scallops, Stir-Fried Squid, and Boiled Spicy Whelks with Chinese Wine—all approved by no less than the late but great Anthony Bourdain!