Few towns in Massachusetts have as delightful a location as Marblehead. Situated on a rocky outcropping 17 miles north of Boston, the town is divided into two parts—the headland known as Marblehead Neck is populated with old-money mansions that are as stunning as the vantage they command; across the harbor, the town center is a pedestrian-friendly collection of old colonial homes and brick buildings shot through with clothing boutiques and eateries.

Like many towns on the North Shore, Marblehead earned its living early from the sea. Founded a year before Boston, it was recognized early as one of the best fishing harbors around. As the Revolution approached, it became a strategic location on the coast, and the British landed there in 1775 to capture ammunition, a year before a similar attempt at Concord (they were turned back without a battle).

Residents also proudly proclaim the town the “birthplace of the American navy” for its role in outfitting and basing the small fleet of schooners that General Washington procured the same year to harass British shipping. These days, Marblehead is now better known as a yachting capital, with a thick forest of white masts covering its sheltered harbor year-round.