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Gloucester and Cape Ann

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Nestled on the island peninsula of Cape Ann on the North Shore of Massachusetts, Gloucester, known as “America’s Oldest Seaport,” was founded in 1623 by farmers and fishermen from Dorchester, England, as the first permanent European settlement in Massachusetts.

This had been the second European attempt at settling the area, and though it initially struggled, Gloucester maintained its status as a fishing village and became a major New England commercial port in the centuries to come. Its gro...