1575?-1585? – Nanapashemet and Squaw Sachem are born.
1590?-1607? – Nanapashemet becomes the great Chief Sachem of the Massachuset. He is the head of a federation that encompasses many tribes and villages and stretches roughly from the Blue Hills of Massachusetts to the Merrimack River in New Hampshire, and from the Atlantic Ocean to the Connecticut River Valley. At the height of his power Nanapashemet is able to summon 3,000 warriors. His main residence is near present-day Salem. He has fortresses in Salem and Marblehead and probably elsewhere.
1600?-1608? – Nanapashemet and Squaw Sachem are married and she gives birth to their first son Wonohaquaham, later named Sagamore John by the English.
1607 – Halley's Comet is seen blazing in the night sky.
Competition over fur-trading with French settlers in present-day Maine sparks the Tarratines War between the Tarratines (Mi'Kmags) and Penobscots.
1609 – Squaw Sachem gives birth to Montowampate, later named Sagamore James by the English.
1614? – Squaw Sachem gives birth to their only daughter, Yawate, later named Abigail by the English.
1615 – Eight years after war breaks out, the Penobscot Grand Sachem is killed, along with his wife and children, by the Tarratines (Mi'Kmag). Nanepashamet sends a war party in defense of his close allies the Penobscot. His war party is successful, killing many Tarratine warriors, and they return home with several women and children taken as prisoners.
1615-1617 - The Tarratines strike back with fierce raiding parties, and they decimate the coastal allies of the Massachuset, including the Wampanoag. All tribes in the area move inland, become unsettled and fearful, and move from place to place.
Nanapashemet moves from his coastal home near Salem, to what likely is his traditional winter hunting and fishing grounds along the Mystic River in present-day Medford. He constructs an elaborate palisade for himself on Rock Hill in Medford, so that one must not only cross a bridge over a moat to get inside, but also climb a ladder. He sends his wife and 4 children to an unknown tribe within his domain somewhere far inland.
1616 – Squaw Sachem gives birth to her youngest son Wenepoykin, later named Sagamore George by the English. He would also be known as George Rumney-Marsh and No-Nose. The birth likely takes place not long before Squaw Sachem goes into hiding.
1617 - A devastating plague sweeps across Massachuset country, and Nanapashemet loses 75%-95% of his people. But because he is so isolated inland inside his fortress, he is spared from the disease. Also, because Squaw Sachem and her children are in hiding so far inland, it is likely that is why they are also spared from the disease.
1618 - Having escaped the pestilence of 1617, the Narragansett look to extend their power. Reduced in numbers, the surviving tribes of the area put up no defense. Most tribes immediately submit in vassalage to the two Chief Sachems of the Narragansett, including Massasoit (who would later ally with the Pilgrims at Plymouth). The Narragansett reach the height of their power, able to summon some 30,000 warriors.
1619 - The Mi'Kmags finally find Nanapashemet and kill him in his palisade at Medford.
1620 - Nanepashemet's wife returns with her four children. Since none of the boys are old enough to rule, custom dictates that Nanepashemet's wife should take over as, "Squaw Sachem." Sadly, we do not know her name and only know her by title. We know of several other, "Squaw Sachems," that existed all over Southern New England – Awasaunks, Weetamoo, etc. – so it is not a unique title.
1621 – Only four tribes remain loyal to Squaw Sachem, and she conducts raids on former members of her husband's federation in an attempt to regain power. She inflicts fear upon Obatinua – the sachem of present-day Boston, who has created a new alliance with the sachem of present-day Weymouth, Chikataubut. They call themselves the Massachuset.
Obatinua meets the Pilgrims. He tells them that, although he lives in Massachuset territory, he is loyal to Massasoit. He also tells them that Squaw Sachem is his enemy, and that he best not linger in one place too long for fear of the Tarratines.
Massasoit meets the Pilgrims at Plymouth. They sign a peace treaty and forge an alliance. Massasoit is said to have, "a potent adversary – the Narragansetts – that are at war with him."
Obatinua, Chikataubut, and 7 other sachems sign a treaty of amity with the Pilgrims for protection. They are reportedly fearful of Squaw Sachem. It is likely the fear of Squaw Sachem, the Tarratines, the Narragansetts, as well as the devastating plagues that have reduced their numbers, that caused these sachems to ask for protection from the English.
1622-1623 – Squaw Sachem places her sons in power at each of the villages that remain loyal to her. Her domain stretches roughly from Charlestown, to Concord, to Marblehead. She continues raids on disloyal villages and tribes from her late husband's former domain.
Wenepoykin, the youngest, becomes sachem of Naumkeag at 8 years old. It is likely a family member helped him rule until he was old enough.
Monowampate becomes sachem of Saugus at 13 years old.
Wonohaquaham becomes sachem of Mishawum, or present-day Charlestown.
As was customary when a sachem dies, Squaw Sachem marries her husband's Pauwau (Physician) named Webcowit. The marriage appears only a formality, however, as Squaw Sachem seems to continue to retain her power. The exact date of their marriage is unknown.
1625 – Present-day Quincy is the site of Merry-Mount. Formerly the settlement of Mount Wollaston, it is now a trading post owned by a man named Thomas Morton. It is a place where much merry-making is taking place. They have beer, rum, and cider. They display their drums and guns. They even erect a may-pole and dance around singing a lewd song in one of the earliest known May Day celebrations in America. Englishmen and Indian women are said to be, "dancing and frisking together," and are described as, "madd Bachinalians."
Squaw Sachem, a regular visitor to Merry Mount, meets Edward Gibbons of Boston, a member of the trading post. They would be close friends for an unknown number of years. Squaw Sachem's disposition mellows considerably, and she never again conducts raids.