Graphic, by US Gen Net

Generation 6
JOHN PYNCHON (mar. Amy Wyllys)

Generation 7
MARY PYNCHON (mar. William Whiting)

Generation 6

The powerful Pynchons – William and his son, MAJOR JOHN PYNCHON – were the first of the Connecticut Valley “River gods”, a title given to the men of wealth and influence whose vision and ambition shaped the future of the country. The town records style him “The Worshipful Major Pynchon”, and later, “The Worshipful Colonel”.

John Pynchon was probably born in 1626 at Springfield, in the Parish of Chelmsford, County of Essex, England. He was brought to Roxbury, Massachusetts at the age of four. When he was ten, his father moved the family to the settlement of Agawam in the Connecticut Valley. In 1641, Agawam was renamed Springfield in honor of John’s father.

He was probably educated at the desks of his parents and the Rev. George Moxon, a graduate of Cambridge University. Rev. Moxon was a lifelong friend of his father and was installed in 1637 as the first pastor at the new settlement of Agawam.

During John’s youth, few in Springfield had much of an education at all. The town was created out of a virtual wilderness. He possessed a superior native intelligence, but to obtain a formal English education such as he received was remarkable.

Along with, and certainly as part of, his studies, John interacted with simple frontier farmers, tradesmen, and Indians of different tribes, obtaining a vast knowledge in the nuances of trade, working in his father’s fur-trading and mercantile businesses. He learned at least one Algonkian dialect. He was one of the very few Puritan officials to understand the nature and importance of intertribal rivalries and warfare. He led his own people along a middle road that ensured peace with the Pocumtuck Confederacy until 1675.

He had ample opportunities to watch his father’s conduct in public offices and on the bench as a magistrate and judge in Springfield. As a result, at a young age he was prepared to deal with all classes and types of men. He developed the attributes of a country gentleman and an English aristocrat, but with a depth of character rarely seen today.

John and his sister, Mary, were Springfield’s two most prominent children. Not much different than today, yesterday’s children of prominence would get a lot of “press” where possible. You can read an example of that in a charming but romanticized story about the Bay Path, used when the original families migrated to Agawam in 1636.

As he matured, John learned how to think and express his thoughts clearly. His penmanship was strong and clear, entirely unlike that of his father. His journaled business transactions show a lack of system and orderly arrangement. His style of writing, however, seems fresh for the time. In his ledger, he often adds picturesque comments or bits of conversation that reveal a little local color, for instance, describing the leather breeches made for him by John Barber.

John Pynchon was reared in, and maintained throughout his life, the old-school concept of an almighty God. During the ministry of George Moxon, as a youth, he took notes, in a kind of short-hand, the leading points in the sermons, which are now in possession of the City Library. His shorthand was only recently decoded. He believed in and observed the Puritan resignation to the will of God, never questioning His ways or His means. God’s Hand was to be seen in every moment of the day. The Lord’s ultimate responsibility for everything comforted and sustained him in all situations. He believed, for instance, that King Philip’s War was God’s means of punishing a sinful New England, the Indians being divinely appointed to chastize the white sinners.

John Pynchon actually became much more important to the Massachusetts Colony than was his father. He was considered, even up to the time of his death, the “chief man in all the west”. He fit no mould, nor did he conform to any of the familiar colonial types. John Pynchon had style, what we would today call “panache”. There were none other like him; he stood alone in the select company of frontier builders. He chose a public life because it was the function proper to a gentleman.

The scope of John’s life is so broad that I’ve arranged what interested me into subject matter categories.


On the 30th of October 1645, John married AMY WYLLYS of Hartford. She was the daughter of the late Governor of Connecticut, George Wyllys. Marriage greatly enhanced the Pynchon name among the first families of New England.

Go to the

About John, his father wrote, in a letter to Governor Winthrop on October 30, 1645, "My only son is now married & he hath brought home his wife this day to my howse, where he may continue as long as he finds comfort & benefit."


John made his first trip to England in 1656, by this time thirty years of age. He resided either in London or Wraysbury, Buckinghamshire, from the September 10, 1656, until November 3, 1657. Unfortunately, there are no letters from this period.

On January 12, 1659, he placed an order for 50,000 bricks to be burned at Northampton for his new mansion, the bricks to be completed by the 12th of December.

(Click on this picture to see a larger view.)

His new mansion would be the first brick home in the Connecticut Valley. The house was built to connect with the older wooden house of his father, which became a wing of the new brick one. The carpenters and masons were from Windsor. The building was 42 feet long, and 21 feet wide. The walls, thick and solid, rose about 22 feet from the ground to the eaves. The roof was very steep, and the ridge was about 22 feet in perpendicular height above the garret-floor.

The house was intended to be a fortified house and was known as the "Old Fort". During King Philip's War, John was in Hadley with his troops on October 16th, 1675, when the Indians attacked and burned the town. The Pynchon "fort" became a refuge during the attack and subsequent burning of the town.

The Pynchon Fort

The mansion was used by the Pynchon family until it was moved in 1831, to make room for a more modern house. In 1831, it was removed to Cross Street, where it served as a house and laundry. It was again altered in 1883, at which time there were still marks of antiquity about it.

Like most of the leading Puritans, he lacked a sense of humor. He had not even a smidgen of Cotton Mather’s wit, and nowhere in his correspondence do we detect a light note. About everything, he was deadly serious and unimaginative.

On September 28, 1651, just prior to his departure for England, John’s father quietly conveyed to him, all his lands (about 280 acres) and buildings, and all his business enterprises. John also received the same special privileges which had been granted to his father concerning trade with the Indians. On November 27th 1652, all of William’s accounts were closed out. In future years, John made several trips to England in connection with his father's estates.

John Pynchon was the most substantially wealthy person in the upper Connecticut Valley. Western Massachusetts was unoccupied land, which needed first to be cleared and settled, then converted into productive farmland.

Amy Pynchon may have introduced John to the Winthrops of New London and Fishers Island. In time he and John Winthrop, Jr., corresponded regularly, and the two families were close. For more than a year, 1654-1655, Amy lived in the Winthrop household at New London while John Winthrop, Jr., treated her for a lingering ailment. A similar closeness developed with the other rich and influential families of Hartford, providing John Pynchon’s entry to the topmost rank of the governing oligarchy of Massachusetts Bay.

His letters are full of reports of family illnesses. One guesses they were not hardy enough for life on the frontier, even with the help of indentured servants and/or slaves that I am certain they had.

John’s father, William, died at Wraysbury, Essex, England on October 29th, 1662. Around October of 1663, John sailed for England again, where he remained until December 30th, 1664, settling his father’s estate (of which he was the principal beneficiary). After completing his commercial arrangements in England, he returned to Springfield. He visited England several times in connection with his father's estates, before and/or after his father's death.

Life changed on the frontier even during John's lifetime. The deer and beaver were gone, most of the Indians moved west into New York. Now the farmers were producing corn, wheat, and lumber. The life of the frontier, created more by Pynchons than anyone else, was gone forever. From his point of view, he was the agent of God in this process.


John obtained land by purchase or exchange — some in payment of debts; some as an allotment due to his role as a town proprietor; and some by town grants in connection with the erection of mills for corn, grist, or lumber, or ironworks.

In 1659, he petitioned the General Court for a grant of land. He stated that his father, William, had brought over from England several servants, promising them 50 acres of land each, which the Massachusetts Bay Company had agreed should be allowed to each person so coming, and that some of these servants were still asking him for their land.

John Pynchon was also a partner in land speculation with James Rogers, the foremost New London [Conn.] merchant of the 1660s and 70s, and it seems likely they were engaged in joint mercantile enterprises. The statement has been made that Pynchon and James Rogers of New London, as partners in land speculation, "engrossed" over 2000 acres in Groton from small holders. On April 25, 1680, John deeded his Boston and New London properties to his son, John Jr.

It was consistent with the times that the devotion of time and energy to civil service would sometimes be rewarded by the General Court with grants of land, and John occasionally obtained large grants from the General Court. One such grant was made in 1681, the island in the Connecticut River just north of the railroad bridge at Warehouse Point, in Connecticut. Warehouse Point is on the east side, and just across the Connecticut River from Windsor Locks.

Charges against John’s father were once made that he had created a monopoly, and charges were also made against John, that he had used his position and monopoly of wealth in western Massachusetts to accumulate the best lands in the Valley. He paid more in the use of his time, labor, energy, advice, and wealth, than he ever received. The Colony at that time had more land than cash, and land was the only medium in which he could be paid. No one today – or for the last couple of hundred years for that matter – approaches doing what he did for the people in the Valley and the state of Massachusetts with the land, and in light of that, those charges seem ridiculous.

No one was more capable and adept at being a frontier leader than John Pynchon. Settlers knew they were fortunate when John Pynchon was there for he was able and willing to use his capital in getting our new country started, generating new wealth from the land.

The fertility of the Valley soil had drawn many of the original settlers to the Springfield area, but it had been money generated by William Pynchon’s prosperous fur-trading endeavors that stimulated it’s growth and provided the necessary capital to establish other towns north along the Connecticut River.


People were streaming into the Valley and they needed land. John Pynchon was the man to dispense it. He brought together the would-be land purchasers and the River Indians by means of a series of mutually agreeable land deeds. From the Indians, he bought the greater part of the Connecticut River Valley, from Enfield and Suffield in Connecticut up to the northern line of Massachusetts. From these lands, he was important in establishing and laying out the towns of Hadley, Hatfield, Northfield, and Westfield. In addition,

  • 1653 – Northampton: He advanced the purchase price for the founding of Northampton (Nonotuck), Mass. On January 12, 1659, John bought land at Northampton for settlers from Hartford.

  • 1667 – Brookfield (Quabaug), Mass. John was a Founder. The first entries in the Account Book for the Quaboag Plantation are on July 14, 1668 for “bacon, corn, salt, and white meale”. John owned a mill at this settlement. The contract with the mill operator appears below.

  • 1670 – Suffield. Major Pynchon paid the Indians thirty pounds for a six-mile tract of land known as Stony Brooke Plantation and settlement began. Brief history of Suffield, Connecticut.

  • 1673 – Governor John Leverett and John Pynchon projected a new plantation west of Springfield (perhaps Westfield).

  • 1674 – Enfield, Conn. The Massachusetts General Court granted land stretching as far south as Asnuntuck Brook to the Town of Springfield. John Pynchon built the first European structure in what would soon be Enfield, a saw mill on the Brook. The saw mill was destroyed one year later during King Philip's War. The first settlers arrived in 1679 from Salem, Mass., and spent their first winter camping in a shelter dug into the side of a hill; 25 families by the end of 1680.

  • Deerfield, in the late 1600s, was still a frontier outpost, but a small number of absentee landowners retained rights there, such as the three Connecticut Valley ministers who held cow commons in Deerfield. John Pynchon retained considerable land and rights in Deerfield through the 1680s, which extended well beyond ownership of land. In 1685 the Massachusetts General Court granted him 1,000 acres "nere to Millers River, above Dearefeild, & nere ye great river," to start a mining venture, "to finde out metall." As the region’s dominant trader, he maintained many ties to Deerfield. In the 1680s, for instance, at least one-fifth of Deerfield's men were involved with Pynchon in trade, rental, or other form of exchange. He gave long-term leases to tenant farmers who in return for low rents were obligated to build dwellings and barns.

  • On 2 March 2, 1693, John went to Hartford again to promote an expedition to the eastward.


It would require a volume to treat in full of John Pynchon's business transactions, but a selected account here serves to give an example of the scope of his character and work.

The economic life of a community depends on its commercial connection with the outside world. Producing the resources to bring in much-needed European goods was a persistent problem. Fur and wampum fueled the local economy through the 1650s and no one did it better than John Pynchon.

John traded fur directly with the Indians, and through agents at such locations as Westfield, Northampton, Hadley, and Albany. He sent the furs down the river to his warehouse at East Windsor, called Warehouse Point. From there he shipped south to Hartford, Boston and then to England. Shipments of English finished goods would return to stock his “general store”, the largest in the whole area for many years. His mercantile transactions extended up and down the Connecticut in the early years from Northampton south to New Haven. In 1654, he spent the months of July and August in Boston on commercial business; he must have done that on a number of occasions.

Consistent with the dangers of shipping on the high seas during that era, Pynchon’s shipments were subject to, and suffered, piracy, such as in October 1653 when six hogsheads of furs were seized at sea by a Dutch privateer; and again, on July 25th, 1666, a shipment of beaver pelts were lost when the Dutch took John Plumb’s vessel.

From its peak in 1656, the beaver trade went into decline, but still remained an important source of income for John. In 1659, he joined a number of influential merchants of Salem and Boston to form a company having as one of its objectives an end to the Dutch monopoly. John ceased all fur-trading activities, however, in 1673, just a few years before King Philip's War.

The interplay between resources and peoples which produced Pynchon’s wealth had vanished by the end of the 1660s. Now it was to be wheat and other English grains which would make the Connecticut River Valley the breadbasket of Massachusetts and more. From his own vast farming enterprises, or with cash and barter, John obtained corn, wheat, grains, peas, flax, hay, beef, and pork. He was shipping 1,500 bushels of wheat every year to his coastal clients. It was New England wheat that relieved the Virginia famine of 1674.

The English Civil War of the 1640s temporarily dampened commercial relations with the mother country, and at this time, New England merchants increasingly turned to fishing, and to the West Indian trade where there was no market for furs. Shipments abroad kept up the supplies in his store so very much needed in the frontier settlements.

International Shipping. Between 1652-1689 he built, owned or had interests in at least five vessels, engaged largely in coastal trading all the way from Newfoundland to the Caribbean. In April of 1653, he outfitted a ship for the Barbados sugar trade. In 1659-60, John dispatched a ship on another trading voyage to the West Indies. Peleg Sanford, out of Newport, served as his agent in the Caribbean in 1664.

Sugar. John was involved with his brother-in-law, Samuel Wyllys, and Richard Lord, of Connecticut, in the production of sugar on the Cabbage-Tree Plantation, St. Paul’s Parish, Antigua in the Leeward Islands.

On 17 November, 1677, John sent some pinetree shillings (New England money) to “Cousin Richard Lord” of Hartford to take to Antigua “to improve for promoting the designe of the Plantation and sugar work there”.

In an interesting note, on 15 August 1685, in a controversy between Samuel Wyllys and Richard Lord (the owners; John Pynchon was unnamed in this matter), and John Lucas (the lessee), the arbitrators ruled that John Lucas was to deliver to the Messrs. Wyllys and Lord the four African children (Combo, Mingo, Dick, and Jack) that were then on the Cabbage Tree Plantation. (See The Wyllys Papers, in References).

After all these many years involved in the West Indies, he withdrew from planting in Antigua and from the West Indian trade in general in 1689.

Sawmills, Lumber. In 1667, John erected the first sawmill at Springfield. In time, he owned several sawmills. In 1680 began a new lumber business, and on April 27th, he made a shipment of 8,000 feet of boards to Antigua. By the 1690s, he was shipping profitable quantities of lumber and timber products, all out of Warehouse Point on the river to Boston, New York, other New England ports and to the West Indies.

Corn and Grist mills. He owned and operated many mills around the area, including one at Brookfield. On November 28, 1672, John contracted with John Ayres for the operation of the mill, which arrangement was in place until Ayres’ death.

Agreed with G. Aires, to keep my mill at Quabauge and tend it, to grind corn brought there, for one year, he to take the tole allowed, viz., one half peck out of a bushel, on all the corn that shall be ground by one and all; and for his tending the mill, he is to have one third of the tole, I am to have the rest for my part paid. He is to grind all the corn at the mill except Gdm. Pritchard's corn. Gdm. Pritchard having liberty to grind his own corn only.

Trading Goods. On April 20, 1675, he joined in partnership with Timothy Cooper at Albany, for seven years, supplying trading goods. I assume this was Albany, New York.

On the 5th of October of 1684, John received a renewal of his grant of land on the Connecticut for his warehouse, but he must rebuild it within three years. He completed the building in 1685, which indicates he was still in trade at that time.

Mills. In February of 1688, John erected a dam and built a cornmill and a sawmill at Suffield.

Tar and Resin. Stemming, I’m sure, from his lumber business, he had an interest in a plant for the distillation of turpentine and the manufacture of resin in 1692, and at least during the next two years. He suffered much from lameness at this time.

Sheep and Cattle. John raised sheep and cattle for distant markets, wintering sheep near Newport and driving cattle overland to points such as New London and even Boston.

Iron works. In November of 1700, just a few years before his death, he was working on a project with John Eliot of Windsor to erect an ironworks, which project was approved at a town meeting at Suffield. He was also involved in lead mines.

Finance. And all during these years, Pynchon might also finance local artisans, such as blacksmiths, who could furnish goods useful in the Indian trade and to the Valley in general. Not to mention the financing of prospective land owners.


John became a freeman of the Bay colony on April 13, 1648 at the age of 22.

Selectman. Chosen; 1650-1651-1652, but was discharged from this office on November 27, 1652, when he (along with Samuel Chapin, and Elizur Holyoke), by order of the General Court, took their oaths before the selectmen as Springfield Commissioners. In 1659/60, he was again elected and served for about eleven years. And as Town Moderator, to preside at town meetings, with only a few intervals, he continued in this office until 1694.

Town Treasurer. Chosen 1650. Again chosen in February 1659/60, and served for three successive terms. References that he served again as Treasurer (this time as County Treasurer) in 1690 and in 1693.

Town Clerk. Chosen in 1652.

Commissioner. On 27 Nov 1652, John was appointed one of three commissioners to administer justice at Springfield. As such, he was one of the commissioners who received the surrender of New York by the Dutch in 1664.

Recorder. Chosen in November 1652 to record lands, town orders, and "the publike occasions of the Towne." Again chosen in February 1659/60 and served for three successive terms.

Town Committees. Between 1660 and 1685 John was often appointed to committees dealing with everything from town rates, town boundaries, accounts of selectmen, settlement of the county government, county rates, laying out highways, disposing of town lands, establishing mills, lands at Woronoco, poor relief, Indian matters, a new meeting house, defense measures, lands at Freshwater Brook, and land grants to the minister.

Magistrate. Early in 1653, The Pynchon Court Record shows that John took his father’s seat on the bench as magistrate in Springfield, to try small causes. Held court for over 21 years, dealing fairly with both red man and white.

Below is an example of a “small cause”. This involves Samuel Terry, who had been indentured to John’s father, William, in exchange for his passage to Massachusetts. Just prior to his permanent departure to England, William had “bound him out” as an apprentice to learn the art of linen weaving. There appears to have been some relationship of friendship between the elder Pynchon and the Terry family. This was one in a long list of case entries for a court session held on September 24, 1661. Present were Captain John Pynchon, Mr. Samuel Chapin, and Elisur Holyoke, Recorder. There were twelve jurymen.

Samuel Terry and his wife [Ann Lobdell] beinge presented for that they beinge marryed on the 3d of January last they has a Son born the 10th of the 5th month beinge about 12 weeks short of the ordinary tyme of womens going with child: This Corte concluded it maifest that they did abuse one another before marriage: and therefore did adjudge Samuell Terry for his offence and misdemeanor eyther to pay as a fyne to the County the summe of 4 pounds to be paid with 20 dayes or that he and his wife should be whipt on their naked bodys with 10 lashes appice: Samuell Terry chusing the punishment by fyne: his choyce was accepted.

And in another case held on 30 September 1676, Philip Butler was brought before John Pynchon on charges for being drunk. Samuel Terry and Isack Morgan both testified that around midnight while they were on watch, “Philip Butler came to them, and gave them ill and high language: his Toung run excedingly and he spake we knew not what and coming in to the house would not goe out nor be ordered but he said he has as much to doe there as wee thought it were the house we were to watch in: we Judged him Drunk or at lease well in drink” Philip Butler was to pay 10s to the County: and “12d a peice” to the two witneses.

See full text of the contract on Debbie Jeffers’ Terry Family Rootsweb site.

Hampshire County Court:
In March of 1663, the new Hampshire County Court heard its first case, with John Pynchon presiding. Soon afterward, he was chosen to be Assistant in the Council (or Upper House) for Massachusetts, a position he held until 1701.
– Head of the Court of Inferior Pleas and the Court of General Sessions of the Peace of Hampshire established under the Second Charter.
– Justice of the Peace, 1692.
– Judge of Probate for Hampshire County, June 1692 and continued until his death.

Massachusetts General Court:
– Deputy. Appointed in May 1659 to serve as deputy to the General Court; served as such until 1665.
– Assistant under the first Massachusetts Royal Charter, May 1665 until May of 1686.

Governor's Councillor:
1686 – Appointed Councillor to Governor Dudley’s Council, May 1686.
1688-89 – Appointed Councillor to the Andros Council, where he sat until the overthrow of the Dominion of New England (see below). On 21 July John and Wait Winthrop were “persuaded” to visit Hartford to encourage Connecticut to ally itself with Massachusetts under Andros.
1693 – Appointed Councillor. Under the new Massachusetts Charter in 1691, his name had been omitted from the list of councillors; this error was rectified in 1693 and he was appointed annually from then through 1703, when he died in office.
1693-1703 – annually elected under the new charter, and died in office.

He was named to only a few court committees, except those relating to protection and settlement of the frontiers of the colony. For instance, this court’s records, and those of the later Court of General Sessions of the Peace, in a number of instances show him charged with the duty of providing for or maintaining the house of correction at Springfield.

John's last Indian case was in 1696. The Court of Oyer and Terminer* at Northampton, presided over by Mr. Pynchon, convicted four New York Indians for the murder of settlers.

* The “Court of Oyer and Terminer” was a court that could quickly begin to hear (“Oyer”) and determine (“Terminer”) the backload of cases pending, since the regular courts, by law, could not sit until after the election of the Massachusetts General Court.

In the course of his many years of public service, he continually had to deal with the government's reluctance to reimburse him for expenses he had paid with his own resources. For example, in 1696, he petitioned the government for payment of various expenses he had made for the colony which were 4-1/2 years in arrears.

John Pynchon was accepted in the top rank of the government. He conducted many diplomatic exchanges with officials of Connecticut, Rhode Island, and New York. He could defer to higher authority because he respected, rather than resented, those over him. He strove to carry out orders precisely and promptly; was sure of himself, but cautious. He never sought offices, yet often burdensome responsibilities were thrust upon him.


The Dominion of New England (1686-90) was a short-lived administrative union of five New England colonies. Two years later, the Province of New York and both East Jersey and West Jersey were added. The union was decreed in 1686 by King James II as a measure to enforce the Navigation Acts and to coordinate the mutual defense of colonies against the continuing threat of the French and hostile Native Americans.

Unifying the northern colonies for purposes of defense and administrative control was regarded in Britain to be a thoughtful move and not a punitive measure. We thought differently on this side.

Joseph Dudley served briefly as the first president of the Dominion, but was replaced by Sir Edmund Andros. Although Andros was an experienced soldier and dedicated to public service, he lacked the common sense and personal skills to be successful in this position. He followed orders assiduously. He terminated local assemblies, taxed the colonists without the consent of their representatives, and vigorously tried to end smuggling through strict enforcement of the Navigation Acts. This centralized authority from England was highly unpopular. Besides which, he supported the Church of England and accepted the loose behaviors of the English soldiers garrisoned at Boston, which greatly angered many loyalists in the Massachusetts Bay Colony. Read here Wikipedia’s article on The Dominion of New England.

The Dominion caused fury in other colonies as well. For instance, in 1687, Andros was so angered by Connecticut's failure to cooperate with the new regime that he and armed retainers tried to take physical possession of the colony’s charter. According to legend, the Connecticut colonists hid the document within a crevice of an old oak tree.* Following the overthrow of James II in the Glorious Revolution in 1688, the Dominion ceased to exist.

* That old oak tree was called "The Charter Oak" and was on the Gov. Wyllys property.

An online book entitled Wadsworth, or The Charter Oak contains an exciting and entertainly presented account of Connecticut’s opposition to Govenor Andros and the struggle over the Connecticut Charter, and how important that piece of paper was to the citizenry of Connecticut.

The book was written in 1904 by W. H. Gocher, primarily as a family history of the Wadsworth family. Capt. Joseph Wadsworth "secured the Charter of the Colony in a very troublesome season." John Pynchon appears in the account, as well as Amy Pynchon’s brother, Samuel Wyllys, if for no other reason than the Charter Oak was on his property.

The historical original has for many years reposed in "the charter box" in the rooms of the Connecticut Historical Society; the complete charter, the historical duplicate, is exhibited in the Connecticut State Library at the Capitol.


John Pynchon’s first assignment under the First Charter was as Lieutenant of the training band, to which post the General Court of Massachusetts confirmed John Pynchon in 1653. In 1657, he was promoted to Captain of the company.

In the autumn of 1663, he was in touch with the Dutch at Fort Orange about Indian relations. A life of military service, at this place and time in history, more often than not involved dealing in matters concerning Indians, as we will see.

John Pynchon was rarely called upon to act in a military capacity prior to King Philip's War. In August 1664, the General Court sent the Capts. John Pynchon and Thomas Clarke to inform the English commissioners that military assistance by the Bay Colony would be furnished "in reducing the Dutch at the Monhatoes into the obedience of his Majestie". As deputies, both men were signatories to the articles of capitulation consented to later in the month at New Amsterdam.

During the Summer of 1666, the Mohawks destroyed the fort of the Pocumtucks near Deerfield.

In 1669, Chickataubut’s attack on the Mohawks, strongly disapproved of by the Massachusetts authorities, resulted in a total defeat of the Massachusetts tribes and the Indian leader’s death.

In 1671, John was promoted to Sergeant Major of the cavalry company. Before long, he became commander of all the military forces in western Massachusetts. As the principal military officer on the ground, he directed the defense of the new communities against incursions by enemy Indians and the French. This involved, as Colonel of the 1st Regiment of Hampshire County, active service during King Philip’s War (1675) and the first of the French & Indian wars. He was noted for his skill in the management of the Indians, by whom he was greatly beloved.


John Pynchon did not play a conspicuous role on the field. For the most part, he was useful in procuring aid and assistance from the Bay and the Connecticut authorities and in coordinating the activities of the local, the Bay, and the Connecticut forces.

On August 4, 1675, he confirmed Indian intelligence of the attack on Brookfield by the Nipmucks. Immediately, he sent to Hartford for aid in securing Springfield, aiding Brookfield, and giving "present chase" to the Indians. He wrote, "We are very raw and our People of this Towne extreamely scattered so that our owne Place needs all and how soone these Indians may be upon this Towne we know not."

Same date, he told his friend, John Winthrop, Jr., that Philip and a small band of followers were at Ashquoash, about 23 miles from Springfield. They had escaped from the Pocasset swamp on the night of July 29. He urged swift action to destroy Philip, but the Connecticut authorities were skeptical of the intelligence.

A party of English was ambushed on August 25 below Deerfield while pursuing some River Indians who formerly occupied a fort on the west bank between Northampton and Hadley. This was the first combat along the River. The militia disarmed this group. They proceeded to avow great loyalty to the English and promised that they would fight against Philip. And so they were re-armed in hopes they might help out with other hostile groups.

Shortly it became plain they were not trustworthy, and the council at Hadley demanded their arms on August 24 but met a show of defiance. The Connecticut Council attempted to disuade John from disarming the Indians, "least it might prove to be provoakeing or discourageing to our Indian Neighboures." Pynchon was "of a differing mind", which offended some, and he wrote: "When I Recollect things: I cant but conclude that this was a Contrived busyness of the Indians."

The Indians had the whites “marching and countermarching” all over the place, in response to their tactics, e.g., an attack upon Deerfield, the ambushing of forces marching to the relief of Northfield. Pynchon wrote despondently: "When we go out after the Indians they doe so sculk in swamps we cannot find them and yet do waylay our people to there destruction."

On September 8, a council of war decided to give up operations in the field and only garrison the towns. Connecticut disagreed and urged a more aggressive campaign, but a few days after, bolder counsels prevailed at Hadley and Major [Robert] Treat was sent up the River with a large force of Connecticut troops.

On September 21, the Commissioners for the United Colonies at Boston had decided to raise 1,000 men, John Pynchon being appointed commander-in-chief; Major Treat, second in command.

Responding to skirmishes in the neighborhood, John Pynchon went with his troops up to Hadley, and was there when the Indian attack and burning of Springfield occurred on October 5, 1675. Within days, he wrote the following letters of despair.

Sp[ringfield]., Octo., 1675

Dear Son Joseph:

The sore contending of God with us, for our sins, unthankfulness for our former mercies, and unfaithfulness under our precious enjoyments, hath evidently demonstrated that He is very angry with this Country. Fod having given the heathen a large commission to destroy this People — And exceeding havock have they made in this Country, destroying two or three small places above Northampton and Hadley, and lately they have fallen upon Springfield, and almost ruined it by burning of Houses. About 30 or 32 dwelling Houses are burnt down, and some 25 Barns full of corn and hay. The Lord hath spared my dwelling house, but my barns and outhousing are all burnt down, and all my corn and hay consumed, and not anything have I left of food either for man or beast. All my mills, both corn and saw mills, are burnt down. Those at home in this Towne and also those I had in other places and four of those houses and barns to them, were burnt down in this Towne, belongeth to me also, so that God hath laid me low. My farmers also undone, and many in Towne that were in my debt, entirely disabled. So that I am really reduced to greate straites. But it is the Lord's good pleasure it should be so. And he is most Just and Righteous, yea in very faithfulness hath he done it, for the good of my Soule. I have not the least cause to murmur and repine, at the wise dispose of a Gracious God and loving fathe, but desire to acquiesce in his good pleasure, and to lye at his foote in holy submission to his blessed will. This Providence and the unsettled state of this country in reference to this Indian War affords matter for consideration, in reference to your coming over, which I have much desired, and wrote to you for — but now shall leave you to your liberty, not having ground, or seeing cause to put you upon it, further than you shall yourself see reason for it. Though I and your mother should be exceeding glad to see you, yet as tymes are, question whether it be best to come over yet (I mean now) and how God may dispose of us I know not. We are yet here in Springfield, my house garrisoned with soldiers and full of troubles and hurrys. The Lord help us to remember our peace and quietness, and to lament our abuse thereof and heartily and really turne to himself, by unfeigned repentance. The Lord is in good earnest with us, and truly expects our being in good earnest with Him in returning to himselfe. Oh dear Son, how sweete is an interest in Christ Jesus, in these distracting tymes, and it is good knowing in whom we have believed. Treasure in Heaven is abiding, when the greatest worldly enjoyments may soon fail us, and come to nothing. Let us therefore, while we have them, so use them, as not using them — setting loose from them them, and being contented to part with all, when God calls for it. In the improving of the creature, to set loose from it, is a sweete and blessed frame, for I know it is a duty to look after and manage what God hath given us, and in that respect I may call on you to doe your best (in a way of prudence) to settle your Estate in England and in it to advise with Mr. Wichens and Bro. Smith, who I know will afford the best helpe they can, and doe as you are able. I am not able to afford you any helpe, but by the prayers I am always putting up for you, and as God shall enable shall be ready to do my utmost for you.

The Lord in many other ways be good to you and us. How he may deal with us I know not. Where his Providence may cast me, whither to Boston or further, or whether I may live to get out of this place, it is with himself and on that strong Rock I desire to depend for Salvation, here and hereafter. I am in straites and hurrys, and may only add mine and your mothers endeared Love and Affection, to you, and with hearty wishes and prayers for you, commend you to the grace of God in Christ Jesus, and am your afflicted and loving Father,

John Pynchon.


Dear Son: I should not have you troubled at these sad losses which I have met with. There is no reason for a child to be troubled when his Father calls in that which he lent him. It was the Lord that sent it to me, and he that gave it hath taken it away; and blessed be the name of the Lord. He hath done very well for me, and I acknowledge his goodness to me, and desire to trust in him and submit to him forever, and do you with me, acknowledge and justify Him."

To Rev. John Russell of Hadley:

We came to a lamentable and woeful sight. The town in flames, not a house nor barn standing, except old Goodman Branch's, till we came to my house and then Mr. Glover's, John Hitchcock's, and Goodman Stewart's burnt, some with barns, corn, and all they had....They tell me 32 houses and the barns belonging to them are burnt, and all the livelihood of the owners, and what more may meet with the same stroke the Lord only knows."

On October 8, 1675, John Pynchon wrote to Governor Leverett:

Sir I am not capable of holding any Command being more and more unfit and almost confounded in my understanding, the Lord direct your Pitch on a meeter person than ever I was: According to Liberty from the Councill I shall devolve all upon Captain Appleton unless Major Treat return againe.

Maj. John received the news that he had been relieved by Captain Samuel Appleton on October 12, "the Councill having seriously considered the earnest desires of Major Pincheon and the great affliction upon him and his family."

Almost all of Springfield was burned out, many losing all they had. Few in New England, however, lost more heavily in buildings, rents, and goods during King Philip’s War than John Pynchon, and recovery would take a long time. In 1676, he gave up command of the forces of western Massachusetts, principally for family and personal reasons.


Pynchon's military duties, however, did not end with King Philip's War. Like Washington in the next century who often tried to quit but he was too valuable, John was called upon, mostly, it seems, in a diplomatic function. The Mohawks referred to Massachusetts as “Pinshon”. On April 28, 1677, John and James Richards of Hartford made a "long, troublesome and hazardous" journey to Albany on behalf of Connecticut and Massachusetts to renew ancient friendships with the Mohawks and to settle and conclude a "league of Freindship and amity between the English of New England" and the Mohawks. The Mohawks sought protection for the "friendly Indians" and destruction of "enemy" Indians allied with the French, referred to as the "North Indians". By the end of the year, John was back in command of the Militia.

The Mohawk Indians came from New York causing trouble and damage to Massachusetts settlements. In August of 1680, John was sent again to Albany, New York, to confer with the governor, Sir Edmund Andros. For four months, until November, he treated with the Mohawks regarding the depredations they were inflicting upon some of our outer settlements. He was able to establish friendly relations with them. In negotiating a renewal of the covenant, or treaty, the Indians gave him a written answer, which was originally drawn in Dutch, but was translated into English, and recorded in the colony records. The General Court paid him £12 for his work on this.

In 1686, Gov. Edmund Andros made John a Colonel.

On July 27, 1688, a small party of Canadian Indians killed five friendly natives at Spectacle Pond near Springfield. John took prompt measures to improve defense against such attacks, but on the 6th of August the same war party killed six settlers at Northfield. John sent soldiers there at once.

In August and September of 1689, John made another trip to New York with some Connecticut agents. They went to give presents to the Mohawks, to inspire them and their allies to make war upon the French. “Albany is a dear place,” he reported to Boston. From 1689 to 1696, he was preoccupied with frontier defense, especially in dealings with Connecticut and the Mohawks.

In 1690, John sent out scouting parties and provided for all sorts of defensive measures against the French and Canadian Indians.

On May 1st of 1691, a congress of colonies met in New York to coordinate military action against the French. Later that year, in November, 150 Indians from New York settled close to Deerfield for winter hunting, claiming to be friendly. Over the years, he would send reinforcements to Deerfield when that town was experiencing significant and repeated Indian attacks. In his own words, John stated that Deerfielders were “in a sense in the enemy’s Mouth almost, and are often and so continually pecked at.” And as is well known, Deerfield suffered its most tragic attack in 1704. There is a page on this website devoted to the Deerfield Massacre of 1704.

On 12 May, 1692, John travelled to Hartford to ask the Connecticut authorities to supply money, as well as to send men, to fight the French and Indians. Sure enough, it wasn't long (July 20th) before the French Indians attacked Brookfield, and for ten days they were pursued by John’s militiamen. On the 27th of July, two hostile Indians escaped from the prison at Springfield.

A couple of years later, in September of 1694, John and others went to Albany to meet yet again with the Mohawks. And in December, he further strengthened the frontier defenses.

Becoming an old man of 69, in 1695, John's activity in military and Indian affairs came to an end.

On December 12, 1695, John Pynchon was called out of bed by news of a war party near Northfield [Mass.]. He quickly despatched Capt. Colton and 24 troopers up the east bank of the Connecticut River.

At about this time, John ceased working in defense of the western frontier. In November of 1696 he outlined his services at length in a petition to the Governor and the General Court for “a meete Compensation for his Past and already chearful service hithertoe in this time of War.” About a year later he was awarded £10 for his “extraordinary service and expenses with the regiment under his command, lying frontier to the enemy.”

In July of 1698, two settlers were killed by Indians at Hatfield and two others taken captive. John Pynchon wrote a letter to Gov. Bellomont of New York and laid the blame on their “counterfeit friends,” the Scagadacooks, accusing them of having a hand in all the Indian outrages in the Valley since 1688. The governor, however, took no effective action to curb these Indians.

But wait!! We see Mr. Pynchon again involved in military affairs. In December of 1702, a list of the militia and civil officers of the province shows John Pynchon was Colonel of the 1st Hampshire regiment, and had mustered over 800 soldiers. Here's what happened. In June that year (just seven months before his death), some French were ranging the Hampshire woods and hunting with the Indians. John and Samuel Partrigg wrote a report, and as a result, the Connecticut Council ordered that all civil and military make strict search and cause the strangers to be apprehended and sent down to Boston to give account of themselves to the governor. In July the Council advised that the Governor write Pynchon to send his Lieutenant Colonel to Deerfield to view and have the fortifications repaired, covering the work with a scout out of other towns, and to perform the same task at Brookfield.


The Colonial authorities had great confidence in John Pynchon’s ability and all during his long service in the General Court, there was scarcely an important question concerning boundaries, or where tact and diplomacy were needed, that he wasn't given the task of bringing about a peaceful resolution.

For instance, in 1671, John negotiated with Connecticut over its boundary with Massachusetts. In what must have amounted to much labor, he prevented encroachments by the expansionists of Connecticut onto Massachusetts land. In 1680, he was appointed with Joseph Dudley to establish the boundary line between the two states. He was one of the committee to make the final settlement of the boundary line between Springfield and Northampton in 1685.


Amy Wyllys Pynchon died on January 9, 1699, at age 74.

"The Honourable Colonel John Pynchon, esquire, was sick and died in the seventy-seventh year of his age." He died in Springfield, “about sun-rise” on January 17, 1702/3. He had outlived most of his contemporaries, being characterized by one diarist as “an old man and full of days”. His only surviving child was John Pynchon Jr., who had become a merchant in Boston and later removed to Springfield.

His lengthy funeral sermon was delivered by a well-known Northampton minister named Solomon Stoddard. One passage provides a fitting eulogy:

Observe, That God has removed one that has been along while Serviceable. That has been improved about Publick Service for above Fifty Years: he has been Serviceable unto the Country in General, and in special among our selves. He hath had the principal management of our Military Affairs, and our Civil Affairs; and laboured much in the setling of most of our Plantations, has managed things with Industry, Providence and Moderation. He has been careful in time of War and as there has been occasion, has been a Peace Maker among us, and helpfull in composing differences: he has discountenanced Rude and Vicious Persons, bearing his Testimony against Them.

"It is to be feared that we shall feel the sorrowful effects of his removal a long while . . . He was honourable and had great influence upon men in Authority abroad, and upon the People at home, and had more experience by far, than any other among us.

He was a father to the country.

The final settlement of Pynchon’s estate was not made until 1737 when it was valued at £8,446.16.6 of which only £165/18/2 consisted of personalty.

CHILDREN of JOHN & AMY WYLLYS PYNCHON All born at Springfield, Massachusetts

  1. Joseph Pynchon, born 26 July 1646. Joseph, boarded at Cambridge with Goodman Beale while preparing for entrance to Harvard College, from which he graduated in 1664. He became a doctor, practicing in Boston, Massachusetts, and died, unmarried, on 30 Dec 1682.

  2. John Pynchon, born 15 Oct 1647. John's father estalished him as a merchant at Boston in the autumn of 1669. He mar. Margaret Hubbard and became a Colonel. He died 25 April 1721. His grandson, William, (1723-1789) wrote a diary of remarkable interest, covering the entire period of the American Revolution.

  3. MARY PYNCHON, was born on 2 or 28 Oct 1650. She was probably some time later stricken with poliomyelitis. She married Joseph Whiting of Westfield, Mass.

  4. William Pynchon born 11 Oct 1653. He died 15 Jun 1654 at 8 months of age.

  5. Mehitable Pynchon, born 22 Nov 1661. He died 24 July 1663 at 1 year 8 months of age.

Generation 6

MARY PYNCHON, was born on 2 or 28 Oct 1650. She was probably some time later stricken with poliomyelitis. She married JOSEPH WHITING of Westfield, Mass., the son of William and Susannah Whiting.

Go to the


Colonial Justice in Western Massachusetts (1639-1702): The Pynchon Court Record. Ed. Joseph H. Smith. Boston: Harvard University Press, 1961.

The Name of War: King Philip's War and the Origins of American Identity. Jill Lepore. New York: Alfred A. Knopf, 1998, pp. 78-80 passim.

Record of the Pynchon Family. Pgs. 6-7. Settlement of estate of John Pynchon.

The Pynchon Papers. Vol. I: Letters of John Pynchon, 1654-1700. Ed. Carl Bridenbaugh. (Boston: The Colonial Society of Massachusetts, 1982). Publications, Vol. 60.

The Pynchon Papers, Vol. II: Selections from the Account Books of John Pynchon, 1651-1697. Ed. Carl Bridenbaugh.

Pynchon, John. Account Books of 1651-1705. 6 vols. Connecticut Valley Historical Museum, Springfield, Mass. Vol. II, p. 215.

Pynchon, John. Hampshire County Court Records (Wastebook). Apr. 1663 - Jan. 1672. Connecticut Valley Historical Society Library, Springfield, Mass.

Pynchon, John. Magistrate Book, 1639 - 1702. Connecticut Valley Historical Society, Springfield, Mass.

William Pynchon Papers, 1640-1647. Massachusetts Historical Society: Manuscripts Call number(s): Ms. N-760.
One narrow box of papers related to Pynchon's defense against charges by the Connecticut General Court related to his trading of corn with the Mohawk Indians of the Connecticut River Valley (now Mass.). The charges maintained that Pynchon raised the price of corn for his own economic gain. Included here is Pynchon's defense to the Church of Windsor, Conn. from which he sought public support after being fined by the General Court. The Church was unconvinced by Pynchon's attempted defense.

The Pynchons of Springfield. Founders and Colonizers (1636-1702). Frances Armytage and Juliette Tomlinson. 1969. Pg. 15.

William Pynchon. Merchant and Colonizer 1590-1662. Ruth A. McIntyre. 1961. Pgs. 10-11, 21.

William Pynchon, the Founder of Springfield. Samuel Eliot Morrison. 1931.

Cabbage Tree Plantation – See The Wyllys Papers, Vol. VIII, Item 595.

Connecticut Valley History Museum. Springfield, Massachusetts.

Labor in a New Land: Economy and Society in Seventeenth-Century Springfield. Stephen Innes (Princeton University Press, 1983).

Letter to Sir H. Vane, from Gov. Endicott and his council of Assistants. 3 Mass. Hist. Coll. I. 35.

Hampshire County Probate Court Records. Connecticut Valley Historical Museum. Settlement of John Pynchon's estate.

History of Western Massachusetts. Pg. 88.

Records of the Massachusetts Bay in New England 1628-86. Nathaniel B. Shurtleff. Boston, 1853-54. Vol. III. Pp. 82, 105, 215, 230.

The New England Quarterly, 60/2 (June 1987) 296-299.

A New England Town, The First Hundred Years: Dedham, Massachusetts, 1636-1736. Kenneth Lockridge. (New York, 1970). Pg. 76.

Peaceable Kingdoms: New England Towns in the Eighteenth Century. Michael Zuckerman. (New York, 1970). Pg. 219.

The Town of Roxbury: Its Memorable Persons and Places. Drake. 1878. Pg. 12.

The First Century of the History of Springfield. Vol. 1, ps. 80. Henry M. Burt. Springfield, Mass., 1898.

Springfield 1636-1886. Mason A. Green. (C. A. Nichols & Co., 1888).

Springfield 1636-1986. Ed. Michael F. Konig and Martin Kaufman. Springfield Library and Museums Association, 1987.

Bremer, Francis. John Winthrop: America's Forgotten Founding Father. New York: Oxford University Press, 2003.

The Winthrop Fleet of 1630. Banks. 1630. Pp. 53-54.

The Wyllys papers; correspondence and documents chiefly of descendants of Gov. George Wyllys of Connecticut, 1590-1796 George Wyllys (Hartford, Connecticut Historical Society, 1924). In regards to litigation concerning the Cabbage-Tree Plantation, see principally, pp. 281-87, 295-96, 313-16, and 383-85.


The Cambridge Agreement – presented online at The Winthrop Society website.

Hampden County, Mass. – a USGenNet Website

Soldiers in King Philip’s War
Soldiers In King Philip's War From 1620-1677. George Madison Bodge. 1906. This online book draws from the ancient account books of Mr. John Hull, Treasurer-at-war of Massachusetts Colony, from 1675-1678. Webmistress Debbie Jeffers. A USGenNet website.

History of Springfield. Vol. II.

Good Site for Pynchon Family

William Pynchon Genealogy.
On the website by of "New England Ancestors of Forrest King" (Oct. 24, 2003). Click "edit" and then "find on this page", search for "pynchon".

The Terry Family website
Terry’s apprenticeship bond and much more interesting stuff. The webmistress is descended also from William and John Pynchon.

University of Massachusetts website: The Connecticut River, and William Pynchon.

Memorial Hall Museum Online: The Digital Collection. Deerfield, Massachusetts.
Home Page.
The Pynchons and the People of Early Springfield.
Lesson 4. By Stephen Innes.

Massachusetts: American Local History Network, hosted by USGenNet. Kathy Leigh, Webmistress.
Home Page
The Bay Path and Along the Way, Chapter 3 of the online book by Levi B. Chase (Norwood, Mass.: The Plimpton Press, 1919).
A charming, romanticized story about the Bay Path, which features John Pynchon and his sister, Mary.

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Last Updated - 7 January 2011

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