Cape Ann is a peninsula in northeast Massachusetts made up of four towns: Gloucester, Rockport, Essex, and Manchester-by-the-Sea.

Gloucester
Gloucester is America’s oldest seaport, settled in 1623. Situated at the center of Cape Ann, Gloucester has one of the finest harbors in Massachusetts and remains one of the busiest fishing ports on the Eastern seaboard. Visitors are drawn to Gloucester’s rich history, natural beauty, incredible beaches, fresh seafood, and on-water activities, such as the popular whale watch excursions. Gloucester also hosts a sizeable number of artists on Rocky Neck, the oldest working art colony in America. This beautiful city holds within its limits three smaller villages. Lanesville can be found on the way out of Gloucester between Ipswich Bay and the historic woods of Dogtown.  It is a very charming and eccentric village whose community hardly strays from the shore. Annisquam is located just minutes off scenic route 127, which wraps around Cape Ann. Annisquam’s center village has the atmosphere of a quaint family-oriented New England  retreat. Magnolia is a village located just above Manchester-by-the-Sea in the southernmost part of Gloucester and boasts some of the best sweeping views of Cape Ann. Gloucester is composed of a diverse group of year-round and summer families who have been drawn to Cape Ann for generations because of its traditional beauty and livelihood.

Rockport
At the northern-most tip of Cape Ann lies the quaint town of Rockport. Settled in 1690, Rockport quickly became a leader in granite cutting; many of these outcrops can be seen today at various quarries. A host of interesting shops and galleries are located on Bearskin Neck and surrounding Rockport’s charming harbor, which is still home to an active fishing fleet. Rockport is one of the country’s oldest artist colonies and boasts some of the most widely painted seaside landscapes in the world, including the coastal shack known as Motif #1.

• Incorporated: 1840
• Distance from Boston: 37 miles
• Total area: 17.59 square miles
• Population: 7,282

Essex
The Essex River, home to some of the best clam flats in the world, forms and contours of the Town of Essex. The river has also played a significant role in shaping the history of Essex. In the past, shipbuilding was the primary industry in Essex, as it was the site of the construction of over 4,000 schooners. Many of the schooners built in Essex were constructed for use from the port of its neighbor, Gloucester. Today, Essex attracts thousands of visitors to its many antique and specialty shops, fine dining establishments such as Woodman’s award winning seafood, and beautiful scenery. Tours of the river by boat and kayak continue to ensure its continuing prominence in the life of the Town.

• Incorporated: 1819
• Distance from Boston: 25 miles
• Total area: 15.94 miles
• Population: 3,260

Manchester-by-the-Sea
When arriving from the South, Manchester-by-the-Sea is the first Cape Ann community you will find. Manchester-by-the-Sea is a residential community wrapped around one of New England’s most picturesque harbors. Visitors are attracted to the small town New England charm of Manchester-by-the-Sea’s quaint shops, fine dining, and historic buildings. New England natives and visitors alike are attracted to the town and its old-fashioned grace and historic prominence along with its beautiful clean beaches and prime location.

• Incorporated: 1645
• Distance from Boston: 25 miles
• Total area: 7.7 square miles
• Population: 5,526