Gloucester Dories

Discover Cape Ann

Perched on the North Shore of Massachusetts, Cape Ann contains all the best of New England. Quaint, picturesque towns, granite coastlines interspersed with sandy coves, historic mansions and working fishing boats. First settled in 1623, the region's history is well preserved in both our buildings and culture. While the land was difficult to cultivate, the vast resources of the sea enabled Gloucester to become, at one time, the largest and now America's oldest seaport. The success of the fishing, shipbuilding and merchant vessels brought more commerce to the area and as life became easier, the beauty of the area was discovered. Cape Ann became the summer residence and favorite vacation destination for many families from Boston, New York, Philadelphia and even as far as Chicago and Milwaukee. Artists flocked to Cape Ann for inspiration. Some could not leave and we boast the oldest working art colony in the country. Recreational boaters moored their yachts and sailboats in our harbors and rivers. Restaurants to this day serve fish brought in daily by our fishermen, clams dug in our estuaries and lobsters trapped right off shore. Stores sell antiques found hidden away and modern handcrafted works of art in the form of pottery, jewelry and furniture. Cape Ann, locally and lovably known as 'the Other Cape', has been able to insulate itself from the overdevelopment often seen in coastal communities. We like the relaxed atmosphere that we have been able to preserve and still enjoy the finer things in life. After a day at the beach or on the water, you can still enjoy a night at the theater and gourmet dinner in town. And we are even luckier than that. With Boston, Salem, and Newburyport within 30 miles and coastal Maine only a 90 minute drive, Cape Ann is Calling.


Centrally located along New England's picturesque coastline, Gloucester makes the perfect home-base for day trips to Boston, historic Lexington and Concord, witchy Salem, the outlet shopping and exploring in Kittery, Ogunquit, Kennebunkport and Portland, Maine.

For more on things to do click here.

Gloucester, founded in 1623, was the first settlement in Massachusetts Bay Colony by the Dorchester Company, the first fishing expedition sent from England. Settling near our current downtown, they used the high, clear field of Stage Fort Park to set up fishing 'stages' for drying their catch. Life was very difficult and farming the rocky soil was near impossible. As you make your way around Cape Ann you can see the granite ledge sitting just under the surface and erupting through the soil. Granite quarrying was pursed in earnest in the mid-1800's but had all but disappeared by 1930. Many of the abandoned quarries are now used as water reservoirs and swimming in the summer. A beautiful example of a granite quarry can be found at Halibut State Park on the northern tip of Cape Ann.

Other early famous visitors to Cape Ann were the French explorer Samuel de Champlain and Captain John Smith of England. In 1606, during his second visit, Champlain named Gloucester harbor 'Le Beau Port' on a hand drawn map. In 1614, Captain Smith bestowed the name 'Tragabigzanda' to the area. Apparently, Captain Smith was fond of the ladies as this was the name of a Turkish princess. King Charles thought it best to rename the Cape after his mother, Queen Anne. Eventually, the 'e' was dropped and the name stuck.

Officially incorporated in 1642, the town green was located at Grant Circle (the first rotary). You can visit a first period house on Cape Ann right here. The White-Ellery House dates from 1710 and is open for tours the first Saturday of the summer months. While most will agree that 300 years is old, Gloucester's oldest house, a square-log style house that dates from 1645, was built 365 years ago. The Thomas Riggs House, named for the first schoolmaster, is located across from Annisquam and is now a bed and breakfast.

The local economy was comprised of fishing, small farms and logging. The center of the island was cleared and lumber was used for ship building and construction to all the communities south to Boston. In 1693, this area was settled, sparsely farmed and kept clear for 200 years. The area became known as Dogtown, for the widows of fisherman lost at sea kept dogs for protection before they turned to witchcraft. The last inhabitant died in 1830 and the settlement has gone to ruin. Scattered with stone walls, old root cellars and mysterious messages carved into the rocks, Dogtown has become a challenging venue for hikers, mountain bikers, historians and nature lovers.

Gloucester is geographically perfect for fishing. There is a deep and protected harbor. We are close to abundant fishing grounds of Georges Bank, Grand Banks, the Gulf of Maine and more. One of the top ten ports in America, Gloucester fisherman land cod, haddock, halibut, swordfish, flounder, sole, bluefish, bass, scallops, mussels, clams, lobster and more. Different methods of fishing make for a varied scene in our harbor. Some boats go out for a few hours, some for a few days and some for weeks at a time. Two movies filmed in Gloucester show the fishing industry in the 19th century and the 20th century, Captain's Courageous and The Perfect Storm.

They also show the dangers of going out to sea. Over 10,000 Gloucester fishermen have been lost to the sea. Half of these have been immortalized in lists stretching up the stairway of City Hall. Listed by year, it is sobering to see some of the really bad years, the obvious family members and that recent years still must be included. In 1925, 'the Man at the Wheel' Fisherman's Memorial Statue was installed on Stacy Boulevard as a monument to 'They That Go Down To The Sea In Ships'.

The on-shore support for the fishing industry has grown along with the catch. Gorton's of Gloucester was the first processor to 'flash-freeze' fresh fish to sell nationwide. Gloucester Seafood Display Auction conducts live auctions daily to participants that can bid on-line. Cape Pond Ice, established in 1848, still provides the ice that fish are packed in after being caught. There is cold storage, marine railways, bait vendors, boatyards, marine equipment and suppliers, boat surveyors, net makers, processors and seafood brokers and retailers.

Gloucester harbor also provided something besides fish. Artists flocked to our area starting in the mid-1800's. The stunning scenery, mystical light and bustling harbor inspired almost every American artist of note during the next 150 years. Many settled together in a small peninsula of land that jutted out from East Gloucester into the harbor - Rocky Neck. Rocky Neck Art Colony is America's oldest working art colony featuring the galleries of many different artists, shops and restaurants.

Gloucester has had a long love affair with the ocean. From the first fishing schooner launched in 1713 to the inspiration for famous painters throughout the ages, we have lived, worked and breathed the ocean for centuries. We love the crashing waves of a fierce nor'easter, the gentle surf of the summer, the steel gray of an overcast day, the bright blue that is sharp and clear and even the fog banks that slink across the rocks and blanket the houses without warning and then steal away just as silently.

Tourism exploded on Cape Ann in the last century. Trains brought affluent families to East Gloucester, Manchester and Annisquam for the summer months. Large rambling hotels sprung up all along the coastline. Boats hailing from Gloucester Harbor now took out weekend fishermen and touring couples. Watching the whales that congregate off our coast became a popular attraction that has become a multi-million dollar industry and earned Gloucester the name "Whale Watching Capital of the World".

Working artists found a market for their paintings and galleries opened along with many charming shops and gift stores. These have grown today to include many antique stores, especially on Essex's Main Street. Exquisite handcrafted furniture, custom printmaking, local seaglass jewelry and more can be found along Gloucester's Main Street. Museums celebrating the diverse and colorful history opened in restored houses and buildings of every era. And, of course, the abundance of fresh fish. Clambakes, steamed lobsters, the invention of the 'fried clam', and fillets of haddock prepared fresh and gobbled up by those from far away are favorite memories of generations of visitors. Now Gloucester welcomes returning generations from all over the world for a family vacation, romantic get-a-way, or peaceful retreat from the real world.


Originally known as Sandy Bay, the northern end of Gloucester became the town of Rockport in 1840. Rockport had a small fishing village and many summer estates but was also know for the beautiful granite that came from its many quarries. These quarries are now abandoned and used as the towns water source for many and as swimming holes for the few families that still own them. Halibut Point State Park has a beautiful quarry you can visit. This picturesque village is now home to shopping, galleries and restaurants, as well as many beautiful beaches. Rockport has always been fiercely independent most notably by the protest by the village wives lead by Hannah Jumper. In 1856, a group of 200 women destroyed all the alcohol in town and declared Rockport 'dry' and it remained so for 149 years. Some restaurants may now serve alcohol with a meal but there are still no bars or liquor stores in town. Rockport is also home to Motif No.1, a red lobster shack that has been the most often-painted building in America.


Essex, settled in 1634 and incorporated in 1819 is located on the landward side of Cape Ann. The north side is mostly marsh stretching into Ipswich Bay. Home to the clam beds that are harvested for the fried clams that were invented in Essex. Also the one mile strech of Main Street is home to many antique stores that range from a $1 treasure to furniture worth 10's of thousands.


The Town of Manchester-by-the-Sea was included in a grant of land to the Massachusetts Bay Colony made in 1629 by Charles I, who signed the charter in that year. By June of the same year the first ship, the Talbot, dropped anchor in Manchester Harbor carrying settlers who were attracted by "the promise of a safe harbor, streams of water, the sheltering hills and an abundant opportunity for building fishweirs, which offered an almost ideal spot for the planting of a new settlement." Prior to the settlers’ arrival, the Agawams, a tribe of the Algonquins, inhabited all of eastern Massachusetts. The chief, or Sagamore, who ruled in this region was named Masconomo. He was a friendly, peace loving man whose tribe was decimated by a plague soon after the arrival of the settlers. Manchester became "Manchester" in 1645, when the people of "Jeoffereyes Creeke" requested and were granted the village name. Before that, the area was part of the town of Salem, and before that belonged to the Algonquin Indians. The settlers acquired land by purchase or by "peaceful possession" until 1700, when a final payment was made to the grandson of Masconomo. At that time, the Native Americans relinquished all right, title, and interest in the land then comprising this township. Fishing and seafaring were the chief livelihoods of the early settlers. At one point the town had more than 40 sea captains commanding vessels. In the mid-1800s Manchester became a summer resort for the wealthy and well known. Presidents, princes, and ambassadors were among the many distinguished people who vacationed here. Notables from the theatrical world were attracted to the town, particularly after the opening of the Masconomo House, an elegant hotel at the corner of Beach and Masconomo Streets built by Junius Booth, brother of the infamous John Wilkes Booth. During this period, because there were many Manchesters in New England, it became vogue to call the town "Manchester-by-the-Sea." The usage so irked Dr. Oliver Wendell Holmes that he headed his letters to Manchester friends "Boston-by-the-Charles." With a 12.8 mile tidal shore line, Manchester is probably best known for its beautiful beaches, a renowned yachting harbor, and commercial lobstering

Discover Salem

Roger Conant led a group of Gloucester settlers to more sheltered land after struggling through three years on Cape Ann. they found more fertile land at the mouth of the Naumkeag River and in 1629 named their settlement Salem for Shalom, the Hebrew word for peace. Salem is probably most widely know for the 'Salem Witch Trials'. From January of 1692 until October, more than 150 men and women were accused and imprisoned for the practice of witchcraft. Barbara Bishop was the first 'witch' hanged in Salem on June 10th. Eighteen men and women were subsequently hanged and one crushed to death before Governor Phipps put an end to the admissibility of spectral evidence. During the 1700's, Salem grew into a very successful shipping port and by 1790, the richest city per capita in the country. Fishing, shipbuilding, and international trade fed the economy and the results can be seen today in the impressive Federal mansions throughout the city. The Peabody Essex Museum, founded by the sea captains in 1799, will take you through Salem's most prosperous periods along with impressive examples of their trade with China, India and the West Indies.

Discover Boston

Boston, just 30 miles south of Cape Ann, is filled with history, arts, shopping and more. After a short train ride into North Station or go by sea on the Salem Ferry, you can walk the Freedom Trail, take in a show, concert or a Red Sox game. Visit any number of museums including the Museum of Science, Museum of Fine Arts, Boston Children's Museum, the Constitution Museum and Ship and many more. Fanueil Hall and Quincy Market for shopping and ethnic cuisine is close by to Boston Commons. Take a look here for so much more.

Discover Points North

Ipswich, Crane's Beach Reservation and Crane Estate - On the other side of Essex, you can find the town of Ipswich. With the greatest number of houses built before 1725 in the country and identified with informational plaques, Ipswich is a great example of early colonial history. Tour the Whipple House (1677) for first period architecture and then cross the street to the visibly more affluent Heard House (1800). Quaint downtown with shops and eateries are just over the river that winds through town.

Another must-see is the Crane Reservation. The Crane Estate at Castle Hill (1928) is the focal point of the Crane Reservation which includes a 5.5 mile beach with walking trails among the dunes and full services and Castle Neck and seven islands in the Essex River Estuary.  The Crane Estate is open for tours and hosts many events throughout the summer.

Newburyport and Plum Island - Just past Ipswich, you can follow Route 1A into Newburyport, a coastal town with lots of shopping and great restaurants. Just before the downtown, take a right to Plum Island. A barrier island that is mostly nature preserve, you can explore the walking paths, beaches and wildlife.

Kittery Outlet Shopping and Coastal Maine - Kittery and Freeport, Maine have long been famous for their outlet shopping. All within 90 minutes with Kennebunkport and Portland in between make a great day trip that is a lovely drive. Don't forget to stop at LL Bean.