40 miles NE of Boston, 7 miles N of Gloucester
This lovely little town at the tip of Cape Ann was settled in 1690. Over the years it has been an active fishing port, a center of granite excavation and cutting, and a thriving summer community whose specialty appears to be selling fudge and refrigerator magnets to out-of-towners. Rockport is an entertaining half-day trip, perhaps combined with a visit to Gloucester.
There's more to Rockport than just gift shops. It's home to a lovely state park, and it's popular with photographers, painters, jewelry designers, and sculptors. Winslow Homer, Fitz Henry Lane, and Childe Hassam are among the famous artists who have captured the local color. At times, especially on summer weekends, you'll be hard-pressed to find much local color in this tourist-weary destination. But for every year-round resident who seems startled when legions of camera-wielding visitors descend on Rockport each June, there are dozens who are proud to show off their beautiful town.
Out of season, especially January through mid-April, Rockport is pretty but somewhat desolate. The year-round population is large enough that some businesses stay open, though many keep reduced hours.