Situated at the craggy tip of Cape Ann on a hazardous coast (hidden coves made it a favorite of rumrunners and smugglers), Gloucester, Massachusetts, was settled as a fishing colony in 1623.
Located 40 mi/65 km northeast of Boston, activities in the area still center on the sea, and local maritime bravery inspired Sebastian Junger's 1997 book, The Perfect Storm. Whale-watching boats leave from the town pier April-October. Do go, but remember that the whales aren't on a schedule, even if you are.
The wharfs of Rocky Neck are home to an artists colony and a semiprofessional theater that produces the works-in-progress of playwright Israel Horovitz. Nearby is Beauport: The Sleeper-McCann House, the dreamy house of interior designer Henry Davis Sleeper, who infused the 40 rooms with the decorating and architectural styles of the 18th and 19th centuries.
Much odder is Hammond Castle, which was built by eccentric inventor John Hays Hammond Jr. Its hodgepodge of Roman, medieval and Renaissance elements includes a drawbridge, Roman baths and a laboratory Hammond had built for his experiments.
The Cape Ann Museum houses an impressive collection of the paintings and drawings of native son Fitz Hugh Lane, whose 19th-century seascapes hauntingly depict the clipper ships and schooners so prevalent then.
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