The boundaries of Gloucester originally included the town of Rockport, in an area dubbed "Sandy Bay".

Native Americans inhabited what would become northeastern Massachusetts for thousands of years prior to the European colonization of the Americas.

[6] At the Cape Ann settlement, a legal form of government was established, and from that Massachusetts Bay Colony sprung.

The area was abandoned around 1626, and the people removed themselves to Naumkeag (in what is now called Salem, Massachusetts), where more fertile soil for planting was to be found.

This new permanent settlement focused on the Town Green area, an inlet in the marshes at a bend in the Annisquam River.

This area is now the site of Grant Circle, a large traffic rotary at which Massachusetts Route 128 mingles with a major city street (Washington Street/Rt 127).

Here the first permanent settlers built a meeting house and therefore focused the nexus of their settlement on the "Island" for nearly 100 years.

Unlike other early coastal towns in New England, development in Gloucester was not focused around the harbor as it is today, rather it was inland that people settled first.

In 1700, the selectmen of Gloucester recognized the claim of Samuel English, grandson of Agawam sachem Masconomet, to the land of the town, and paid him seven pounds (equal to £1,327 today) for the quitclaim.

Fishing, for which the town is known today, was limited to close-to-shore, with families subsisting on small catches as opposed to the great bounties yielded in later years.

Commerce and capitalism transformed the society, making it much more closely knit with extended families interlocking in business relationships.

[10] Early Gloucestermen cleared great swaths of the forest of Cape Ann for farm and pasture land, using the timber to build structures as far away as Boston.

One feature of the construction of these houses was that under one side of the floor was dug a cellar hole (for the keeping of food), supported by a foundation of laid-stone (without mortar).

These cellar holes are still visible today along the trails throughout the inland part of Gloucester; they, and some walls, are all that remain of the village there.

While still part of the town of Gloucester, the people of Second, or "West", Parish now constructed their own meetinghouse and designated their own place of burial, both of which were in the hills near the marshes behind Wingaersheek Beach.

The granite rises straight behind a house, encroaches on each side, and overhangs the roof, leaving space only for a sprinkling of grass about the door, for a red shrub or two to wave from a crevice, and a drip of water to flow down among gay weeds.

Gloucester is home to the Cape Ann Transportation Authority, which serves the city and surrounding towns.

Gloucester's most famous[citation needed] (and nationally recognized) seafood business was founded in 1849 as John Pew & Sons.

Besides catching and processing seafood, Gloucester is also a center for research on marine life and conservation; Ocean Alliance is headquartered in the city.

In the late 19th century, Gloucester saw an influx of Portuguese and Italian immigrants; they were seeking work in the town's flourishing fishing industry, and a better life in America.

During the Catholic celebration, St Peter's Fiesta, relatives of fishermen past and present carry oars representing many of the fishing vessels which call Gloucester their home.

[34] Gloucester's scenery, active fishing industry, and arts community have attracted and inspired painters since the early 19th century.

Other painters subsequently attracted to Gloucester include William Morris Hunt, Winslow Homer, Childe Hassam, John Twachtman, Frederick Mulhaupt, Frank Duveneck, Cecilia Beaux, Jane Peterson, Gordon Grant, Harry DeMaine, Emile Gruppe, Stuart Davis, Joseph Solman, Mark Rothko, Milton Avery, Barnett Newman, William Meyerowitz, Joan Lockhart, Theresa Bernstein, Samuel Nigro, and Marsden Hartley, and artists from the Ashcan School such as Edward Hopper, John Sloan, Robert Henri, William Glackens, Emile Gruppe, Carl W. Illig, and Maurice Prendergast.

Gloucester is the birthplace of Marvel character Dane Whitman whose superhero alter ego is the Black Knight.

Bewitched season 7, episode 5, "Darrin On A Pedestal" (October 22, 1970) was set and partially filmed on Gloucester.

Spenser: For Hire, season 2, episode 1, "Widow's Walk" (October 4, 1986) was set and filmed in Gloucester.

Over the years, plays developed at the Gloucester Stage Company have gone on to critical acclaim, on and off Broadway, nationally and internationally.

[citation needed] The group draws theatre-goers from Gloucester, neighboring North Shore districts, and the greater Boston area, as well as seasonal residents and tourists.

It also has exotic waterfront homes now converted to museums, including Beauport, built 1907–1934 by designer Henry Davis Sleeper in collaboration with local architect Halfdan Hanson, said to raise eclecticism to the level of genius.

Preceded by a nine-day novena of prayers, the festival highlights include the blessing of the fleet and the greasy pole contest.