[2] Rockport is located approximately 40 miles (64 km) northeast of Boston, at the tip of the Cape Ann peninsula.

Before the coming of the English explorers and colonists, Cape Ann was home to a number of Native American villages, inhabited by members of the Agawam tribe.

Samuel de Champlain named the peninsula "Cap Aux Isles" in 1605, and his expedition may have landed there briefly.

Richard Tarr, a granite cutter and the first settler of the Sandy Bay Colony, lived in the area that is now Rockport in 1680.

Rockport had consisted primarily of large estates, summer homes, and a small fishing village while Gloucester was becoming increasingly urbanized.

Although the demand for granite decreased with the increased use of concrete in construction during the Great Depression, Rockport still thrived as an artists colony—which began years earlier due in part to its popularity as a vacation spot known for its rocky, boulder-strewn ocean beaches, its history as a prominent fishing harbor, and its mentions in media like that of Rudyard Kipling's Captains Courageous.

A red fishing shack on Bradley Wharf in Rockport, known popularly as "Motif Number 1", has for years been one of the most famous sites on Cape Ann as the subject of hundreds of paintings and photographs, and is visited by aspiring artists & tourists alike from all over the world.

[6] Sales at stores were not allowed until March 2019, when a local market was granted a liquor license and began to sell beer and wine.

98 built a 27-foot (8.2 m) scale model of "Motif No.1" for the Legion Parade, which was held in Chicago, Illinois, site of the 1933 World's Fair.

Designed by Aldro Hibbard and Anthony Thieme, with participation by the RAA, Board of Trade and townspeople "from high to low", the float was commissioned in June, completed by the end of September, and driven in daylight only, from Rockport to Chicago, in less than a week.

[10] Finns and Swedes were often lumped together as one group, and as Historian Jonathan Schwartz suggests, “a generalized "Scandinavian" identity for the Swedish and Finnish immigrants, at least in the eyes of the New England community”.

Originally, Finns were brought to Pigeon Cove and the Rockport Granite quarries to break strikes in the early 1890s, but eventually became one of the most militant groups to fight for workers' rights.

The Boston Globe provided many reports of the Finns being particularly strong labor activists, refusing to cut deals and threatening those who tried to go to work during the strikes.

[15] The Rockport Granite Company attempted to bring in Italian laborers from Boston to act as strikebreakers in the spring of 1899.

[18] On April 20, 1899, a group of two hundred Finns rallied and worked its way to the quarry shanties, armed with clubs and stones, eventually converging on the Italian workers who had taken refuge in the boiler house, even going so far as to pull the shutters off the building.

Two explanations are possible for the closing of the quarry—the introduction of new building materials such as poured concrete and quarry workers' continued movement for higher wages into the 1920s.

[10] Swedish and Finnish workers continued to work in the quarries until their closure, and have left a distinct mark on the cultural heritage of Rockport.

Today Rockport is primarily a suburban residential and tourist town, but it is still home to a number of lobster fishermen and artists.

The town's other protected areas include Halibut Point State Park & Reservation, the Thacher Island National Wildlife Refuge, and the Knight Wildlife Reservation on Milk Island, as well as a smaller area just south of Halibut Point run by the Massachusetts Audubon Society.

Places and organizations with artistic or cultural notability include: Rockport is served by thirteen weekday commuter trains to Boston as one terminus of the MBTA Newburyport/Rockport Line.