Marblehead, with its narrow and winding streets, beautifully preserved clapboard homes, sea captains’ mansions, and harbor, looks much as it must have when it was founded in 1629 by fishermen from Cornwall and the Channel Islands. One of New England’s premier sailing capitals, Marblehead continues to attract boats from along the Eastern seaboard each July during Race Week—first held in 1889. Parking in town can be difficult; lots at the end of Front Street or on State Street by the Landing restaurant are the best options.


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