The history of Wilmington begins about 1665 with the first settlers, Will Butter, Richard Harnden and Abraham Jaquith. Massachusetts Bay was first settled nearly 50 years before that.
Of course, there is unknown history of natives going back thousands of years. Some interesting stories, though, can be found. One comes from Lynn & Surroundings, by Clarence W. Holden, published in 1886. He wrote of the first settlers there, and some of the native stories they learned.
The following tale quite possibly would have included travel through what is now Wilmington. Woburn Street is an old native trail, crossing the Ipswich River at Jenk’s Bridge. In early times, it was a ford. Because of the wide swamps along the river, there were no other crossing points from there to the sea. Anyone traveling north would have crossed there.
The easternmost part of Wilmington, very roughly everything east of Route 93, was once part of Reading, and before that, Lynn. Reading was originally called Lynn Village.
From Hobbs: The area between the Charles and Merrimack rivers was the domain of Nanapashemet, chief of the Pawtuckets, who sometimes made his home near the falls of the Merrimack and occasionally on Sagamore Hill, on the coast. But in a long and bloody war with the Tarratines, those terrible fighters of eastern New England, Nanapashemet, the New Moon, had gone down in a crimson sky; and a terrible scourge, occurring shortly after, had so reduced the numbers of Indians that when the first settlers came, there were only scattering villages here and there, presided over by local .
The old warlike spirit of the noble red men had given place to a more peaceful disposition, ready to receive whatever in the way of benefits the white men might bring. They were entirely willing to sell whatever land the settlers desired, and did not hesitate to sell the same parcel as many times over as they could find a purchaser — a practice prolific of trouble for the settlers and business for the courts.
The Indians are represented to have been tall and well-formed, and one impressionable writer speaks of “the unparalleled beauty” of the Indian maidens, describing them as having “very good features, seldom without a come-to-me in their countenance, all of them black-eyed, having even, short teeth, and very white, their hair black and long, broad-breasted, handsome, straight bodies, and slender thin limbs, cleanly, straight, generally plump as a partridge.”
Hobbs writes of Indians in the legendary history, with verse from poet John Greenleaf Whittier: “The pathetic tale of the bride of Pennacook reaches farthest back into the shadowy vista of the past —
A story of the marriage of the chief
Of Saugus to the dusky Weetamoo
Daughter of Passaconway, who dwelt
In the old time upon the Merrimack.
“The story is that Winnepurkit, as Morton has it, or, more properly, Winnepoyekin, son of Nanapashmet, sagamore of Saugus, when he came to man’s estate, made choice, for his wife, of the daughter of Passaconway, the great chieftain of the tribes inhabiting the Merrimack valley.”
“The union of the young people was blessed by the mighty chieftain, and in due time, Weetamoo was seated in her lord’s wigwam on Sagamore Hill, with the broad bay spread out before her door, now shining like a burnished mirror in the sun, and then rolling its angry waves upon the beach in thunderous monotone, or dashing them on the rocks of Little Nahant.
“Before long, however, a homesick longing for a sight of her father filled her heart, and like a kind husband, Winnepurkit sent her home, escorted by some of his most mighty men. The daughter was received with open arms, and the escorts were cordially entertained and graciously dismissed. After a short stay, she signified a desire to return to her noble husband. Her father sent messengers to Winnepurkit to notify him of the desire of his wife, and to request the Saugus sachem to dispatch a suitable guard to escort his wife back through the wilderness to her home.
“But here, an unexpected difficulty arose, for Winnepurkit told the messengers to carry word to his father-in-law, ‘That when his wife departed from him, he caused his own men to wait upon her to her father’s territories, as did become him. But now that she had an intent to return, it did become her father to send her back with a convoy of his own people.’
“Both men were of high spirit and neither would yield, and so the poor princess was forced to remain with her father, at least for a time.”
Tradition has it, however, that her woman’s wit found a way through or around the difficulty, and that she, after a while, made her way back to her husband’s home.
Whittier, however, gives a different and tragic ending to the tale. In his poem, the heart-broken Bride of Pennacook determines to return alone. She steals away from her attendant maidens, launches her frail canoe upon the swollen and threatening Merrimack, and is instantly swept
“Down the vexed center of that rushing tide,
The thick, huge ice blocks threatening either side,
The foam-white rocks of Amoskeag in view
With arrowy swiftness —
Down the white rapids like a sere leaf whirled
On the sharp rocks and piled-up ices hurled,
Empty and broken, circled the canoe
In the vexed pool below, but where was Weetamoo?”