How Did Gloucester’s Founding Shape Its Future?

Blyman Bridge. 1923
Edward Hopper (1882–1967)

by Mary Ellen Lepionka

As a municipality, Gloucester historically was regarded as poor compared to other seaside towns in Massachusetts. I wondered why and found answers in our early history. Massachusetts Bay Colony policies destroyed the productivity of the first comers to Cape Ann, and the newcomers who followed them were farmers who could not turn a profit on Cape Ann’s soils. Gloster Plantation was underfunded from the start. Its harbor never received enough investment to achieve its potential as an international port of trade. Later, the wars of the 18th and 19th centuries benefitted other towns but left Cape Ann depopulated and depressed. Historical circumstances shaped Cape Ann’s prospects, just as early childhood experiences can shape us in ways we may come to understand but find hard to change.

John Endecott (1588-1655)

In 1628 the New England Company, which became the Massachusetts Bay Company, sent John Endecott to govern the Old Planters at Salem Village (relocated members of Rev. John White’s failed Dorchester Company plantation on Gloucester Harbor) and to oversee Cape Ann. The next year the Company obtained a royal charter to start a colony and sent a fleet to Salem with 350 settlers, the so-called Higginson Fleet, named for the minister who wrote an account if it. Then in 1630, they sent John Winthrop with a much larger fleet to govern the Massachusetts Bay Colony. Masquenominet (Masconomet, Pawtucket sagamore) and his entourage canoed out to Winthrop’s vessel as it lay at anchor (in Beverly Cove or Mackerel Cove) and went aboard to welcome him. Winthrop gave trinkets to the Indians, relieved Endecott, and moved the capital from Salem to Dorchester. The Massachusetts Bay Colony then established a General Court.

The General Court promptly declared null and void all deeds of land bought directly from the Indians without the Court’s permission! Anyone living on such lands were squatters! They were to be evicted and the land redistributed to newcomers! This ruling (missing from what we are taught about the history of Massachusetts) had a devastating effect on all first comers. William Jeffreys, for example, lost his holdings at Jeffrey’s Creek and Jeffrey’s Neck and his lucrative fishing grounds on Jeffrey’s Ledge at Ipswich.

John Winthrop (1588-1649)

Independents and ex-Plymouth fisherfolk in Cape Ann’s nooks and crannies—Kettle Cove, Lobster Cove, Pigeon Cove—quickly added themselves to the rolls of the plantation or became part of the new town by gifting their land to it on condition of getting it back through redistribution or being allowed to live and make a living on it! In a long letter called The Planter’s Plea, John White begged the General Court to let the Old Planters in Salem-Beverly keep at least the land on which their houses stood, which was granted. First comers at Jeffrey’s Creek also were permitted some acreage for a town (renamed Manchester-by-the-Sea).

The four ships John Winthrop brought to New England, 1630
William F. Halsall (1841-1919)

The scale of this disaster makes one wonder if the plight of first comers—some of whose descendants still live here—is the deep-time source of local distrust of state government, prevalent in Gloucester and other coastal Massachusetts towns down to the present day. The earliest settlers and entrepreneurs had been disenfranchised, displaced, and potentially pauperized overnight. If they lacked ownership of their land, they lacked the chief means of upward mobility—other than participation in the slave trade by supplying corn, barley, and fish to the Bermuda and Caribbean slave plantations.

The fur trade was no longer a source of income. After a hundred years of dealing with Abenaki middlemen in the French fur trade, the Native people of Essex County were no longer interested and in any case, had already hunted beaver to near extinction. And the domestic shipbuilding and maritime industries had barely begun. The sketchy Cape Ann economy, interrupted, was soon thoroughly regulated and taxed, although to encourage maritime industries, the General Court excused fishermen from military training, duties on salt, and tithes on their catches.

The General Court redistributed the land first comers had borrowed, bought, or taken from the Indians to fleets of newcomers during the Great Migration, in which an estimated 15,000 to 20,000 people emigrated to New England between 1630 and 1642.

Newcomers to Newbury, Rowley, and Ipswich included prosperous North Country weavers and woolen manufacturers and gentlemen farmers. They flourished on the rich alluvial soils of their broad floodplains and built country estates. Beverly and Beverly Farms likewise had large expanses of prime agricultural land.

First comers to Cape Ann (Gloucester, Rockport, Essex) had been fishermen from the West Country—Devon, Dorset, Hampshire—but most newcomers were illiterate and even less well-off farmers from Gloucester, Warwick, and Worcester. On Cape Ann, they were homesteading on marginal land unconducive to large-scale agriculture and easily damaged by over-grazing. Over time, first cattle and “rother beasts”, then sheep and pigs, and finally goats were all the land would support. Harvesting pole pines for the Royal Navy and salt marsh hay for animal fodder became the leading export industries.

Plantation proprietors petitioned the General Court for clear legal title to their lands, becoming towns with selectmen or aldermen. They were required to pay (or repay) the Indians to obtain quitclaim deeds. Gloster Plantation, established in 1638, and then the Town, incorporated in 1642, complied by renting land from Masquenominet! This is a little-known, possibly hidden, fact that you will not find in local archives. Gloucester rented to buy, paying the Indians over time. Over the next 50 years, they paid in kind—bushel baskets of Indian corn—in lieu of cash. The last recorded installment was paid in 1682. Gloucester paid its taxes and military dues the same way—in Indian corn, barley, and peas, with frequent requests for quota reductions and abatements.

In 1700/1701 Samuel English and Masquenomenit’s other grandchildren sued Gloucester in General Court—another little-known/hidden fact—and they won their case. The General Court ordered Gloucester to pay the balance owed in cash—£7 for the 10,000 acres, including Essex.

The newcomers to Cape Ann were farming among the rocks in sandy, acid soils, and after centuries of inshore overfishing, fishermen were having to sail five miles out to Stellwagen or Jeffrey’s Ledge (or 60 miles out to George’s Bank in the Gulf of Maine, and later even farther) to find market fish in any quantity. More important, the start of the English Civil War in 1641 put an abrupt end both to mass migration and to aristocrats’ investment schemes for making Gloucester Harbor into a prosperous international port.

In 1642 the General Court had invited a wealthy merchant prince in the tobacco trade, Maurice Thompson, to oversee Gloucester Harbor and to create and regulate shipping through a canal between Ipswich Bay and Massachusetts Bay. Such a canal—the Cut— would make shipping between Canada and Virginia both shorter and safer by avoiding the Cape, which was already littered with shipwrecks. The port also would serve as a distribution center for transatlantic trade. Thompson had a great flow of capital to invest from wealthy landowners in England, such as Richard Rich, the Earl of Warwick, who had a special interest in developing coastal New England.

The relationship between the Indian Village, Gloster Plantation, and the planned port at Duncan’s Point.

Governor Endecott had houses, docks, and warehouses built for Thompson at Duncan’s Point, where Harbor Loop is today, but the merchant prince did not accept the offer. He sent agents to check it out but never came. Greater riches were to be made in the Caribbean and South America. In 1643, in an effort to develop Gloucester on its own, the selectmen employed a Puritan from Plymouth, Richard Blynman, to make the Cut and serve as the town’s minister. Per usual, they paid in kind in lieu of a salary, offering some land and a free hand to profit from running a ferry or toll bridge across the Annisquam.

Things didn’t go well between the strict new pastor and the people of Gloucester. In 1650 he and his party, including the first town clerk, left for Connecticut Colony. The Cut was abandoned and soon filled in. It was dredged from time to time, but opportunities to salvage the dream were passed up again and again. By the time the Cut was reopened—in 1823 and again in 1907—it was too narrow and shallow to serve the international shipping industry, and steamships had less need of both the shortcut and the safety.

During the 18th and 19th centuries, Cape Ann men were out to sea or at war most of the time. Population declined. Provisioning fishing vessels became Gloucester’s main industry. Vessels were prey during the Anglo-Wabanaki and French and Indian Wars, the Revolutionary War, the Napoleonic Wars, and the War of 1812. It’s said the British replenished their ships’ stores by raiding sheep pastures in Dogtown. Other coastal towns capitalized on home front industries that could provide war materiel—soldier’s uniforms, canvas for sails and tents, gun parts. Gloucester, in contrast, provided service as privateers, troop transports, and merchant marines. Later, men left for the California gold rush even as the granite industry was starting. But exploitation of immigrant labor meant that the quarries enriched their owners and corporate chiefs more than the towns. Men who did not fish left Cape Ann for jobs. The fishing industry became hugely successful, but dependence on fishing had given Gloucester a risky, undiversified economy—a kind of monoculture gradually leavened by summer resorts, artists, retirees, tourists, and (we can only hope) new industries.

History is a great teacher. As individuals and as municipalities, historical circumstances shape our prospects, but they do not necessarily determine them. We make ourselves, and we are not poor. That things are hard to change doesn’t mean they can’t.


Mary Ellen Lepionka lives in East Gloucester and is studying the history of Cape Ann from the Ice Age to around 1700 A.D. for a book on the subject. She is a retired publisher, author, editor, textbook developer, and college instructor with degrees in anthropology. She studied at Boston University and the University of British Columbia and has performed archaeology in Ipswich, MA, Botswana, Africa, and at Pole Hill in Gloucester, MA. Mary Ellen is a trustee of the Massachusetts Archaeological Society and serves on the Gloucester Historical Commission.

2 thoughts on “How Did Gloucester’s Founding Shape Its Future?

  1. This is a marvelous essay!
    Thanks so much, Mary Ellen.
    Much food for thought.
    A couple of comments.
    One, Joe Garland used to make the point that the fishing industry “monoculture” was a great asset for Gloucester — that in times like the Depression, people always bought food, so Gloucester fared better than other places. The fisheries continues to be a major resource for our economy, with current risks being in NMFS management. But these can be resolved. So, not necessarily a weakness to have an emphasis on the fishing industry. Just needs to be rebuilt. Ports like Portland, Maine, were encouraged to diversify their economies, found it didn’t work, and have successfully refocused back onto food and seafood industries. These sectors also produce solid middle-class jobs, in comparison to low-wage tourism and very high-wage, low employment science projects.
    Also, while the owners of the granite companies might have extracted more wealth out of the granite quarries than the Finnish immigrant workers were able to, nevertheless Lanesville had an incredibly rich and productive culture and community.
    In fact, it may be true that poorer communities, because residents need to rely on each other so much more than rich people do, have more dynamic, cooperative, and caring cultures? Perhaps Gloucester’s relative poverty, in a strange way, has been its salvation over the centuries? (Not that that formula works now or in every community.)
    So much to ponder and talk about! Thanks for the research and thoughts!


  2. Wonderful research you have done I read it twice just to let it sink in they was so much information, I also enjoy the painting at the very top of the story looking at the cut Bridge that little slab at the very front of the painting 75 years ago I was sitting there when I was 10 years old fishing with a hand line it seems like a million years ago, and I guess it is thank you for bringing back some memories to me that were wonderful for the first 17 years of my life


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