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For four centuries Gloucester has lived by the sea. Settled in 1623 on Cape Ann, it calls itself America's oldest seaport, and its fishing fleet inspired Kipling's Captains Courageous and Sebastian Junger's The Perfect Storm. The bronze Man at the Wheel still looks over the harbor in memory of the thousands of fishermen lost at sea.
The city is also an artists' town. Fitz Henry Lane painted its harbor light, Winslow Homer and Edward Hopper worked here, and Rocky Neck remains one of the oldest working art colonies in the country. Portuguese and Italian fishing families shaped its churches, festivals and food.
Come for sandy beaches like Good Harbor and Wingaersheek, a whale watch to Stellwagen Bank, the eccentric Hammond Castle and fried clams eaten on a wharf by the water. Rockport and Essex are next door, and Boston is about an hour away by train.
Bronze statue of a fisherman at a ship's wheel, unveiled in 1925 on Stacy Boulevard to honor Gloucester men lost at sea. Plaques nearby list thousands of names going back to the 1700s, and a later memorial honors fishermen's wives and families. Walk the boulevard at sunset for harbor views.
Lighthouse at the tip of Eastern Point guarding the entrance to Gloucester Harbor, with the current tower dating to 1890. Next to it, the Dog Bar Breakwater stretches almost half a mile into the water, and you can walk its granite blocks. Wear good shoes; the stones can be slippery.
Church built in 1915 by Gloucester's Portuguese community, with blue twin bell towers and a statue of the Virgin holding a schooner. It has a carillon and models of fishing vessels inside. Visit outside of service times; it stands on Prospect Street, a short uphill walk from the harbor.
Castle built in the late 1920s by inventor John Hays Hammond Jr. on the cliffs of Magnolia, filled with medieval and Renaissance architectural pieces, a great hall and a huge pipe organ. Ocean views from the grounds are superb. It is open seasonally and for special events, so check dates first.
Downtown museum of Cape Ann art, history and culture, holding the largest collection of works by marine painter Fitz Henry Lane, along with granite quarrying and fishing exhibits. Its galleries also show modern artists who worked here. Plan about two hours, and visit its second campus when open.
Summer home of designer Henry Davis Sleeper on Eastern Point, with dozens of themed rooms packed with collections of colored glass, folk art and antiques, all overlooking the harbor. Run by Historic New England, it is open from late spring to fall by guided tour. Reserve a time slot ahead.
Small peninsula in East Gloucester where artists have painted since the 19th century, among them Winslow Homer and Edward Hopper. Today it has working studios, galleries and waterfront restaurants on narrow lanes. Parking is tight, so leave the car in the lot at the entrance and walk in.
Broad sandy beach facing the Atlantic, with tidal pools and Salt Island just offshore, reachable on foot at low tide. The water is cold but clear, and the sand is soft. Parking is paid and fills early on hot weekends; watch the tide if walking to the island so you are not stranded.
Calm beach at the mouth of the Annisquam River with warm shallow water at low tide, large granite boulders and views of the Annisquam lighthouse. It is a favorite with young children. Arrive very early in summer because the parking lot often fills by mid-morning, and check the tide chart.
Whale watch boats leave Gloucester Harbor for the Stellwagen Bank National Marine Sanctuary, where humpback, fin and minke whales feed from spring to fall. Trips last about four hours with naturalists on board. Bring layers and motion sickness remedies, since it is cool and choppy offshore.
Festival run by the Italian-American fishing community each late June, honoring St. Peter, patron of fishermen. Highlights include the greasy pole contest over the harbor, seine boat races, processions, music and food stalls. The St. Peter's Square area gets very crowded, so arrive early.
Wooded reservation of about 600 acres managed by The Trustees, with carriage roads and trails through hemlock forest, granite ledges and the Great Magnolia Swamp. Paths are shaded and mostly easy. Pick up a trail map at the Western Avenue entrance, and wear sturdy shoes for the rocky sections.
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