With pre-Revolutionary architecture and secluded beaches near Boston, this sprawling city is a rare combination of urban spirit and historic charm.
Photo: Tara Donne
Main Street downtown hosts funky coffee shops, antiques galleries, and indie bookstores. Gloucester is most active during the summer season, when the beaches, outdoor dining, citywide block parties, and Cape Ann Farmers' Market shine. But whale watches continue throughout the fall, and nature walks are popular year-round.
Left: The Bookstore of Gloucester on Main Street