33 miles NE of Boston, 16 miles NE of Salem
The ocean has been Gloucester's lifeblood since long before the first European settlement in 1623. The French explorer Samuel de Champlain called the harbor "Le Beauport" when he came across it in 1606, some 600 years after the Vikings. The harbor's configuration and proximity to good fishing gave it the reputation it enjoys to this day. If you read or saw The Perfect Storm, you'll have a sense of what to expect here.
Gloucester (which rhymes with "roster") is a working city, not a cutesy tourist town. It's home to one of the last commercial fishing fleets in New England, an internationally celebrated artists' colony, a large Portuguese-American community, and just enough historic attractions. Allow at least half a day, perhaps combined with a visit to the tourist magnet of Rockport; a full day would be better, especially if you plan a cruise or whale watch.
Down by the Sea
On Stacy Boulevard west of downtown Gloucester is a reminder of the sea's danger. Leonard Craske's bronze statue of the Gloucester Fisherman, known as "The Man at the Wheel," bears the inscription "They That Go Down to the Sea in Ships 1623-1923" (the phrase is from the 107th Psalm). Several hundred yards west is a memorial to the women and children who waited at home. As you take in the glorious view, consider this: More than 10,000 fishermen lost their lives during the city's first 300 years.