Masconomet and Nanepashemet

In 1630 the sagamore of Agawam, Masquenominet, famously met Governor John Winthrop (1587-1649) on the Arbella between Manchester Harbor and Beverly Harbor off Salem Sound (not in Salem Harbor as often erroneously reported). Winthrop was coming to replace John Endicott as governor of the newly formed Massachusetts Bay Colony. Endicott was with remnants of the Dorchester Company and new arrivals from England at Naumkeag (Beverly-Salem) at the time (and their story is forthcoming). Winthrop promptly moved the capital from Salem Village to Dorchester and in 1634 sent his son, John Winthrop Jr. (1606-1676), to Agawam to evict squatters who had bought land directly from the Indians prior to the establishment of the Massachusetts Bay Company and to found a plantation there (Ipswich). The goal was to prevent any designs the French might have on extending their influence further down the coast on the Gulf of Maine. Winthrop Jr. arrived with 11 men from Charlestown whose families would constitute the founding population and set about purchasing and appropriating Indian land and resources.25

Representations of Masconomet 26


In 1638, Winthrop Jr. paid Masconomet £20 for a quitclaim deed to some of the sagamore’s personal landholdings. This first deed specifies farmland along present-day Argilla Road between Labor-in-Vain Creek and Chebacco Creek, including Sagamore Hill. Winthrop Jr. noted this sale in his papers, but did not occupy “Argilla Farm” or Sagamore Hill or Castle Hill on Plum Island Sound beyond. He was intent instead on founding colonies in Connecticut. Later in 1638, Masconomet sold the entirety of “Agawam” (Salem to the Merrimack River) to the Ipswich colonists for another £20. Winthrop Jr. sued in the Massachusetts General Court for reimbursement of the purchase price for the first deed and won. In 1644, after moving to New London, Connecticut, Winthrop Jr. deeded Castle Hill to his Deputy Governor and brother-in-law, Samuel Symonds. In 1910 the Crane family acquired the property, which is now managed by the Trustees of Reservations.27 The locations of Agawam Village and Masconomet’s homestead on the Castle Neck River and information about the place of the Pawtucket in local history have been suppressed, withheld from the pubic.

The First Deed Masconomet Signed

I Masconnomet, Sagamore of Agawam, do by these presents acknowledge to have received of Mr. John Winthrop the sum of £20, in full satisfaction of all the right, property, and claim I have, or ought to have, unto all the land, lying and being in the Bay of Agawam, alias Ipswich, being so called now by the English, as well as such land, as I formerly reserved unto my own use at Chebacco, as also all other land, belonging to me in these parts, Mr. Dummer’s farm excepted only; and I hereby relinquish all the right and interest I have unto all the havens, rivers, creeks, islands, huntings, and fishings, with all the woods, swamps, timber, and whatever else is, or may be, in or upon the said ground to me belonging: and I do hereby acknowledge to have received full satisfaction from the said John Winthrop for all former agreements, touching the premises and parts of them; and I do hereby bind myself to make good the aforesaid bargain and sale unto the said John Winthrop, his heirs and assigns for ever, and to secure him against the title and claim of all other Indians and natives whatsoever.

Witness my hand.

28th of June, 1638

Witness hereunto,

John Joyliffe,

John Downing,

Thomas Coytimore,

Robert Harding,

Masconomet, His Mark

 The next year for another £20 Masconomet deeded the rest of Agawam—most of Essex County–to Winthrop as well. Did Masconomet know what he was doing when he signed these deeds? Yes, and that’s another story, to come.28

As sagamore, Masquenominet was the hereditary head of an alpha or high-ranking family in his patrilineage. He was the authority figure for the macro-band of interrelated extended families occupying Essex County from the Merrimack River to the North River and from Lowell to Cape Ann. He would have been responsible for allocating and redistributing subsistence areas to the families, which is why he was the one signing the deeds. At the same time, Masquenominet paid tribute to a sachem, a leader from the most numerous and/or most powerful and/or prestigious band, whom the bands chose to lead them all. During the Contact Period he paid tribute to the eldest son of the Massachuset sachem Nanepashemet. The acquired status of sachem is closer to the European concept of chief. When inherited status and acquired status coincided, the roles of sagamore and sachem were sometimes played by the same person.

Masconomet welcomed Winthrop Jr. and encouraged the English to settle, first at defensive sites near the shore. He invited them, for example, to occupy his fort on Castle Island in Castle Neck River, Ipswich. In exchange for land he asked for protection against Pawtucket enemies. Accounts of the Massachusetts Bay Colony record how early settlers of Ipswich aided Masconomet against the Tarrantines, as Champlain had earlier aided the Pennacook and Abenaki against the Huron (Wyandot) and the Mohawk. According to a deposition of William Dixie of Ipswich, for example, given in 1629:

They [the “Agawame Indians”] inform Governor Endecott, that they are fearful of an invasion from the Tarrentines or Eastern Indians. He immediately despatches a boat with Hugh Brown and others, to defend them. Such aid was afforded them several times.29

Castle Island in Castle Neck River, between Castle Neck and Hog Island, Site of Masquenominet’s Principal Fort in Agawam 30

In addition to raiding for corn, the Tarrantines were seeking to avenge their dead from previous campaigns against them by Masquenominet and his allies. In those campaigns the Pawtucket allies may have been seeking to avenge the death of their grand sachem Nanepashemet, killed by Tarrantines in Medford in 1619. Pawtucket sagamores had been clients of Nanepashemet (1575-1619), who led the Pawtucket, Nipmuc, and some Abenaki and Massachuset bands at the time of European contact. A daughter of Masquenominet, Joan, was married to Nanepashemet’s son Wonohaquaham (John), and after Nanepashemet’s death, Masquenominet paid tribute to Nanepashemet’s eldest son, Montowampate (James).  Masquenominet (Anglicized to Masconomet or Masconomo means “Named for the black bear”), was a name bestowed on him as an honorific. His Pawtucket given name was Quonopkonat, which remains untranslated.31

His name appears in all the following ways in the literature: Sagamore John, Indian John, Masquenominet, Masquenomoit, Mascanamenet, Machanomett, Maschanominet, Masconominet, Muskonominet, Muskonomett, Musconominet, Mascquenomet, Mascomonet, Masconomma, Masconnoma, Masconomo. In Mass. Bay Colony records he is known by his Christian name, John, following his conversion in 1640. I chose Masquenominet because that is his how his own descendants, who were literate, wrote his name. His children’s and grandchildren’s Christian surnames include Tyler and English and there are living descendants today.32


Masque (Mask) = “the black bear”

nominet = “one named for”

Algonquians did not use personal pronouns such as he or she, but in English one would be tempted to say “He is named for the black bear.”

After previous failed attempts on his life at his summer retreat on Marblehead Neck and elsewhere, Nanepashemet was finally killed in 1619 by a Tarrantine war party, most likely in retaliation for his support of the Saco of Maine in their attacks against the Tarrantines in earlier years. He was killed in his hidden and heavily fortified log fort on Rock Hill, Medford, north of the Mystic River in what is now the Middlesex Fells Reservation.33

Nanepashemet’s Summer Residence, Marblehead Neck

According to Edward Winslow’s 1621 account, in addition to a stockade of trees Nanepashemet’s fortresses (Winslow also describes another at Naumkeag) included watchtowers; a trench moat with a ramp; scaffolds with ladders; and platforms with shelves to cache arms, including stones to throw to repel the enemy. Defenders included archers, slingshot throwers, spearers, and rock droppers.34

The Massachusetts Bay Colony erected a small historic maker, now missing, along what is now the Mystic Valley Parkway:

Rock Hill—Site of Lodge and Lookout of Nanepashemit. Sachem of the Nipmuc Indians. Mystic, his stockaded village, was about half a mile to the westward near High and Grove streets, West Medford. He was killed in 1619 and succeeded by his widow, the Squaw Sachem.35

 The Tarrantine Wars are taken up in more detail in another chapter, but it is in the context of the chain of vengeance following Nanepashemet’s death that the Tarrantines attacked Agawam on August 8, 1631. At the time, Nanepashemet’s Christianized sons—John (Wonahaquaham), sagamore of Saugus, and James (Montowampate), sagamore of Chelsea, and their wives (daughters of Masconomet and Passaconaway respectively) and their parties—were visiting Masconomet at Sagamore Hill in Ipswich, near Castle Hill and Choate (Hog) Island in Essex Bay. According to the account:

The Tarrentines, to the number of 100, came in three canoes, and in the night assaulted the wigwam of the Sagamore of Agawam, slew seven men, and wounded Masconomet and his cousins John and James, and some others, whereof some died after, and rifled a wigwam of Mr. Craddock’s men, kept to catch sturgeon, took away their nets and biscuit.36

At that time, the Tarrantines also kidnapped Sagamore James’s wife, Wenuchus (or Wennunchus), a daughter of Passaconaway, who was later ransomed and returned.

The Bridal of Pennacook

James was married to Wenuchus in 1629, an event immortalized in a poem by John Greenleaf Whittier (1807-1892). Whittier named the bride Weetamoo (a historical figure from a different story) and the “Saugus Sachem” as Winnepurkit (misidentified as Sagamore George, the third Nanepashemet brother, rather than as James). The poet’s pastoral and elegiac lines reflect both the romanticism and the fatalism of mid-19th century views of Native Americans and their way of life. Here, for example, is an excerpt from Whittier’s “The Bridal of Pennacook”, Part I. The Merrimac:37

O child of that white-crested mountain whose springs

Gush forth in the shade of the cliff-eagle’s wings,

Down whose slopes to the lowlands thy wild waters shine,

Leaping gray walls of rock, flashing through the dwarf pine;

From that cloud-curtained cradle so cold and so lone,

From the arms of that wintry-locked mother of stone,

By hills hung with forests, through vales wide and free,

Thy mountain-born brightness glanced down to the sea.

No bridge arched thy waters save that where the trees

Stretched their long arms above thee and kissed in the breeze:

No sound save the lapse of the waves on thy shores,

The plunging of otters, the light dip of oars.

Green-tufted, oak-shaded, by Amoskeag’s fall

Thy twin Uncanoonucs rose stately and tall,

Thy Nashua meadows lay green and unshorn,

And the hills of Pentucket were tasselled with corn.

But thy Pennacook valley was fairer than these,

And greener its grasses and taller its trees,

Ere the sound of an axe in the forest had rung,

Or the mower his scythe in the meadows had swung.

In their sheltered repose looking out from the wood

The bark-builded wigwams of Pennacook stood;

There glided the corn-dance, the council-fire shone,

And against the red war-post the hatchet was thrown.

There the old smoked in silence their pipes, and the young

To the pike and the white-perch their baited lines flung;

There the boy shaped his arrows, and there the shy maid

Wove her many-hued baskets and bright wampum braid.

O Stream of the Mountains! if answer of thine

Could rise from thy waters to question of mine,

Methinks through the din of thy thronged banks a moan

Of sorrow would swell for the days which have gone.

Not for thee the dull jar of the loom and the wheel,

The gliding of shuttles, the ringing of steel;

But that old voice of waters, of bird and of breeze,

The dip of the wild-fowl, the rustling of trees.

 “Squaw Sachem” was the name by which Nanepashemet’s widow was known. Her real name is lost, but she was not Ashawonks, the “squaw sachem” of the Rhode Island Sacconet band, with whom she is sometimes confused. After her husband’s death, Squaw Sachem married his personal physician, Webbacowet, a shaman (pawaw) of the Musketaquid of Concord, MA. She also formed a new political alliance with the powerful Pennacook shaman and sachem, Passaconaway. This alliance had been cemented through the marriage of her son James to Passaconaway’s daughter Wenuchus. 37

So it was that Masconomet, Squaw Sachem, and Nanepashemet’s heirs all became subordinates or clients of the Pennacook powwaw turned sachem, Passaconaway, who had previously been a subordinate of Nanepashemet. Passaconaway became a legendary leader, as Nanepashemet’s legacy lost its power through the three-part division of his territory among his three sons and through general discontent over having a squaw for a sachem. Like Masconomet and Nanepashemet, Passaconaway counseled peace with the Europeans and survived the contact period in good standing.39