Gloucester's coastal location and its dramatic landscape features — harbor, rivers, uplands and shoreline — were instrumental in shaping the history of the community from the earliest Native American use of the land to the present day.

Prior to English settlement, Gloucester was inhabited by members of the Pawtucket group, who traveled along the rivers and coastline, and also established inland trails. Although few pre-historic archaeological sites are known for the Gloucester area, the presence of Native Americans is well documented by early explorers and settlers.

Cape Ann was used for seasonal fishing until 1623 when the Dorchester Company established a year-round fishing settlement on what was later known as Fisherman’s Field, now Stage Fort Park. Settlement remained sparse until 1642 when the population was sufficient to merit incorporation. Around that time the center of town moved from Fisherman’s Field to near the First Parish Burial Ground and later to the area of present day Grant Circle along Route 128. By the 1740’s the harbor was assuming more importance. Annisquam, Sandy Bay (now part of Rockport) and the Riverdale Mills area were also important early villages. Gloucester's early settlers were mostly farmer/fisherman/carpenter combinations, with a large transient population. Around 1800, trade with European and Asian ports became an important industry. Fishing did not become the primary industry until after the war of 1812.

Major fires in 1830 and 1860 destroyed much of the downtown area. Throughout the 19th century commercial fishing continued to prosper, there was an active granite industry and tourism emerged as an important part of the local economy. During the late 19th and early 20th centuries there was an influx of people from the Canadian Maritimes, the Azores, Finland and Sicily. Gloucester was incorporated as a city in 1873.

The year-round population remained relatively stable between 1915 and 1990, at just over 28,000. The most densely populated areas occur in the central business and downtown, particularly around Gloucester Harbor, as well as in the villages of Magnolia, Lanesville, Annisquam and East Gloucester. Gloucester is also a seasonal tourist community, whose summer population increases by about 40%.

From Gloucester Reconnaisance Report, Essex County Landscape Inventory, Massachusetts Heritage Landscape Inventory Program (pdf document)