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Cliff Calderwood is a travel writer living in rural Massachusetts. He writes extensively about New England where he has lived for the last 31 years with his family and dogs, and a bunch of animals in the woods that have a lot more right to live there than he does - but he watches out for them.

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Cape Ann – Guide to the Other Cape in Massachusetts

Rockport Harbor ImageIf you’re looking for an alternative coastal vacation in New England then pack your bags – and your family – and head to Cape Ann, one of Massachusetts most underrated destinations.

Cape Ann offers historical tours, a proud fishing heritage, vibrant whale watching industry, and a wide variety of natural beauty.

Cape Ann, often know as “the other cape,” is a rocky peninsula that stretches out into the Atlantic. Located thirty miles northeast of Boston,

Cape Ann is comprised of the towns of Gloucester, Essex, Rockport and Manchester-by-the-Sea.  All four of these towns contribute to the fascinating history of Cape Ann, with roots in fishing and logging.

A bit of history: the American colony of Cape Ann was founded in 1624, three years after the Pilgrims landed at Plymouth Rock.  Two ships from the Dorchester Company of England brought thirty-two colonists to the shores of Cape Ann in the interest of starting a plantation and fishing operation.  With some false starts, the settlements along the Cape have endured and left behind a powerful legacy of fisherman and shipbuilders, one that is still celebrated in the numerous historical sites and museums that are scattered throughout the area.

Over the years Gloucester has lost many of residents to the sea and this is commemorated by the famous statue overlooking the harbor. In 1991 the fishing vessel Andrea Gail and crew were all lost at sea in what became known as the “Perfect Storm” off the New England coast. The boat was out of Gloucester.

The arts have long held a position of importance in Cape Ann and two of the oldest artist colonies in the United States are in Cape Ann; Rocky Neck Art Colony and Bearskin Neck are a prime destination for both artists and art lovers the world over. Spend time in Rockport photographing the famous harbor and walk around the galleries and specialty shops and cafes in the town.

Gloucester Memorial ImageMuseums are just one sign of Cape Ann’s dedication to its history and culture.  You can find museums specializing in fine art, historic collections, natural history, and of course nautical history.  In Essex, tour the Essex Shipbuilding Museum and see full-scale construction displays and hands-on exhibits, learning what shipbuilding was like in a time before power tools.

If you have a bent for the fantastic, consider heading to Gloucester for Beauport, known as the Sleeper-McCann House. The house is an elegant arrangement of towers and dovecots and gables whose rooms are each decorated with various historical and literary themes.

If you’re more of an outdoors person and a diver, then Cape Ann offers numerous experiences for every level of experience.  The waters offer extraordinarily high visibility and a wide variety of sea life.

Just off the shore, you can investigate shipwrecks, wall dives and rocky reefs.  At Halibut State Park enjoy the beautiful coastal landscape, and enjoy hiking trails and tide pools in one visit!

Whale watching is big part of the Cape Ann vacation experience, and you and your family should not miss this unique opportunity to see some of nature’s most beautiful and intelligent creatures in their natural habitat. Many of the cruises run out of Gloucester and during the season you can expect to see humpbacks, finbacks and Minke whales. A whale watching tour usually consists of a three to four hour excursion to areas fifteen to thirty miles off from the coast, and many trips are narrated by specialists employed by the tour itself.

Manchester-by-the-Sea ImageWhile Cape Ann is known for its jagged coastline if you’re a beach lover then take a trip to Manchester-by-the-Sea and its Singing Beach.

The beach is a gorgeous family destination for a sand-filled day. The beach gets its name from the squeaking sound it makes when you walk on the sand.

Close-by is a popular rock composite called “Eaglehead” popular for climbing

Finally, fine dining is a watchword in Cape Ann, and you can dine on freshly caught lobster, halibut, haddock and native shrimp, and always find delicious New England chowder and clam strips at nearly every restaurant you visit in any of the Cape Ann towns.

For further suggestions of things to do in Massachusetts then check out our special Massachusetts page here >>>

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Cliff Calderwood
New England Online Magazine

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