In England he was a member of the group of Adventures which later became the Massachusetts Bay Company. William's father, John went to school at New College (Oxford) with the Rev. John White of Dorset, and William was probably acquainted with him before becoming a member of this group of Adventures.

I believe this is an important connection between the families, because later on William will bring Samuel Terry the immigrant to New England. It is believed that Samuel is a descendent of John and Mary (White) Terry. Mary was sister to Rev. John White. Samuel was brought over with a few other boys who were indentured. Samuel on the other hand was apprenticed to Ben Cooley to learn the trade of weaving.
Samuel's grandson Isaac will marry Margaret Downing, daughter of Margaret Pynchon and Nathaniel Downing and great, great, granddaughter to William.

William came to New England with the Winthrop Fleet in 1630 with his wife Anna Agnes Andrews and four children. Ann was the daugter of William Andrew of Twiwell, Northamptonshire, and was a member of a old Warwickshire family.

They settled first at Roxbury where he was the principle founder. Anna died there in the first year and he later married Widow Frances Stamford. He was the first member to join the newly formed Congregational church of Roxbury in 1632.

In 1636 he led a party from Roxbury, among whom were Henry Semith, his son-in-law, Jehu Burr, and Miles Morgan, to the Connecticut River, and began the settlement of Agawam, which he named Springfield, after his hometown in England. He was a magistrate there for many years and made a good deal of money in the beaver trade. He did very well at trading with the natives, becoming the second largest trader in new England.

Willam served as a Massachusetts Bay assistant, from 1630-36, and again from 1642-50/51, and as treasurer 1632-33. Oddly he did not become a Freeman until August 11, 1642, yet he had always behaved as one from the day of his arrival. It may be that it was an oversight, that may have been noticed in May of 1642, when William was elected an assistant again. The first time he had served in a colony office since his removal to Springfield in 1636.

He was in England in 1650 to oversee the publication of his book, The Meritorious Price of Our Redemption. This book held views contrary to the prevalent Calvinistic view of atonement. The publication caused quite a stir in the magistry. The General Court condemned his book as false, heretical, and erroneous, and ordered Rev. John Norton to answer it. The Court ordered the burning of his book in the marketplace of Boston. They also threatened to prosecute William unless he retract his statements publicly and in writing both here and in England. Upon his return to New England, he was hauled before court.

In May, 1651, Pynchon appeared and explained or modified the obnoxious opinions. The judgment of the Court was deferred till the next session in May, 1652. Hoping to give him time to change his mind and attitude in these matters. William, fed up with the persecuting and intolerant spirit of the authorities in the Bay, returned to England, with his wife and son-in-law, Henry Semith, before his court date. Henry returned and he and Ann moved to England late in 1654. He left his son John to care for the business in Springfield. There in 1655, he published a new edition of his book, with additions and other books concerning religion. He died in England in October 29, 1661, at the age of seventy-two. He is buried in the church yard at Wraysbury. He outlived both his wife and daugter Ann who died within a few days of one another in Oct. 1657.

William was the primary force responsible in the establishment of the first court in western Massachusetts and the administration of justice in the region until 1651.

Children of William and Anna are:
1. Ann Pynchon, b. abt. 1618, m. Henry Semith of Springfield, "a godly, wise young man." He was the son of Frances Stamford by a previous marriage.

(1) Their dau. Mary Semith m. April 15, 1665, Richard Lord of Hartford, Ct. (son of Capt. Richard Lord),. He d. Nov. 3, 1685; abt. 49. She m. for a 2d husband Dr. Thomas Hooker of Hartford, Ct., son of Rev. Samuel Hooker of Farmington, Ct., they had no children. By her first marriage she had one child, Richard Lord, 3d, of Hartford, who m. Abigail Wakerman of Boston.
(2.) Hannah Semith, who m. Hon. John Allyn of Windsor, Ct., a son of Hon. Matthew and Margaret Allyn.

2. Maj. John Pynchon, b. abt. 1620 m. Hartford November 6, 1645, Amy Wyllys daug. of George Wyllys and Bridget Young.

3. Mary Pynchon b. abt. 1622, m. Sept. 20, 1640, in Springfield, Elizur Holyoke of Springfield, Mass. He was the son of Mr. Hollioke of Linn, Mr. Pynchon's ancient friend.

4. Margaret Pynchon, b. abt. 1624, m. October 31, 1644, in Springfield, William Davis. He was a wealthy and enterprising Boston apothecary, he was chosen deputy from Springfield several times.

I descend from John and Amy Wyllys Pynchon.

Major John Pynchon (son of William, the settler), was born in England in 1624 or 1625, and came to this country with his father when he was about 5 years old. He married on October 30, 1645, to Amy Wyllys. She was born in England in 1621, the daughter of Governor George Wyllys of Hartford and Bridget Young, Connecticut.

The extent of his education is unknown, but it's likely that he was taught by John Eliot at Roxbury and the Reverend Moxon at Springfield. It is said he was a man of very superior talents, character and social position.

Not much is known about him until November of 1650, when he first held public office where he was selectman and town treasurer. He was chosen selectman again in 1651 and 1652. On Nov. 27, 1652, he was discharged from this office when he, Elizur Holyoke, and Samuel Chapin, took their oaths before the selectmen as commissioners to hear and determine causes.

He represented the town of Springfield in the General Court in 1659, 1662, and 1663, and was for 21 years (1665-86) an "Assistant" in it. He was spoken of and addressed by the title of " The Worshipful" from 1652 to 1660 (when Hampshire County was incorporated).

From 1692 to 1702, he was Chief Justice of the Court of Common Pleas for Hampshire County

He was extremely active in the building of new plantations in the Connecticut Valley. The May 1653 General Court appointed Pynchon, Holyoke and Chapin to divide the Nonotuck (Northhampton) land which the Springfield inhabitants successfully petitioned for, which would be divided into two plantations. In May ,1659, again the three along with two others were selected to layout the boundaries of a town at Norwattocke which became Hadley. Then in May, 1667, came Quabaug, which became Brookfield and later in 1670, Suffield. Other plantations followed as the towns grew. In 1683, the General Court granted the new township of Freshwater Brook below Springfield to be called Enfield.

In a number of cases John assisted the settlement of these new plantations by using his own funds when purchasing the land from the natives. He would be paid by the settlers at a later date. The towns of Northampton, Hadley, Westfield, Deerfield, Enfield and Suffield were purchased in this way.

In 1653, under the First Charter, he was confirmed lieutenant. In 1657, he was made captain and later, in 1671, sergeant major. He was not a military leader with the exception of activity in King Philip's War and later in defence against the native and French marauders. He was unhappy as Commander and Chief and felt he was unfit for the post. The Connecticut authorities rarely took his advice, which he felt led to the eventual destruction at Springfield and to some of the other outlying towns. In King Philip's war, in 1675, his brick house, built in 1660, was used as a fort for defense.

John had his hands in many businesses. He was a large farmer and landholder, fur trader and cattleman. He owned several saw-mills and grist-mills, and was much engaged in public business. Even as far off as New London, where he and New Londoner, James Rogers bought 2,400 acres there in what was probably a land speculation deal.

Sometime around 1682-87, he held interests with his brother-in-law Samuel Wyllys and Richard Lord (who was also a relative though his neice's marriage) in a sugar plantation called Cabbage treen in Antigua in the Leeward Islands. Between 1652 - 1689, he owned or had interests in at least five vessels, largely used for costal trade. In 1692, he had an interest in a plant for the distilling of turpentine. He also held interests in mining ventures.

There are a number of letters to John Winthrop Jr. in which he asks for medication for his wife and daughter. It also appears that Amy spent time at the home of the Winthrops recovering from some illness he was treating her for. Even so, she lived to be a good old age for that time.

He was very active in goverment affairs until his death. He outlived his wife and all of their children with the exception of John Jr. He died about sunrise on Janury 17, 1702-3, at about 77 years. Amy died Jan. 9, 1698-9, at abt. 74 years. The final statement for John's estate was not made until 1737 when it was valued at 8,446 pounds, 16 shillings, 6 pence, of which only 165 pounds, 18 schilling, 2 pence was reckoned as personal property.

Children of John and Amy Pynchon:
4. i. Joseph Pynchon, M.D., b. July 26, 1646, grad. at Harvard in 1664, a physician at Springfield, representative to the General Court in 1681-2, d. unmarried at Boston, Dec. 30, 1682, aet. 36.

5. ii. Col. John Pynchon, b. Oct. 15, 1647, d. April 25, 1721. He married Margaret Hubbard.

6. iii- Mary Pynchon, b. Oct. 28, 1650, m. Oct. 6, 1671, Joseph Whiting of Westfield, and had 2 children:

1. Mary Whiting. b. Aug. 19, 1672.
2. Joseph Whiting, b. Dec. 5, 1674.

7. iv. William Pynchon, b. Oct. 11, 1653, d. June 15, 1674.
8. v. Mehitable Pynchon, b. Nov. 22, 1661, d. July 24, 1663.

I descend from their son John and Margaret Hubbard Pynchon.

5. ii. Col. John Pynchon, was born Oct. 15, 1647, he married about 1672 to Margaret Hubbard, dau. of the N. E. Historian, Rev. William Hubbard of Ipswich, Mass., and Margaret Rogers, dau. of Rev. Nathaniel Rogers of Ipswich and Margaret Crane.

He was Lt. Colonel, and clerk of the courts and register of deeds. He lived at Boston and afterwards at Ipswich and Springfield. He was made judge in 1708, and died on April 26, 1721. She died at Springfield on November 11, 1716. Their children were all born at Ipswich.

Children John and Margaret are:

9. i. Col. John Pynchon, Jr., b. in 1674, d. July 12, 1742.

10. ii. Margaret Pynchon, b. about 1680, m. Aug. 10 1704 in Ipswich to Capt. Nathaniel Downing.

11. iii. Col. William Pynchon, b. in 1689, d. Jan. 1, 1741, set. 52.

I descend from daug. Margaret and Nathaniel Downing

See direct line to my NY Terrys

Other Interesting Pynchon information

Indian Deed to Northhampton:
From: NEHGR vol. 5 - excerpt from the Memorial of the Stibbins Family

Moving the Old Burial Ground in Springfield:
From: NEHGR vol. 5 - excerpt from the Memorial of the Stibbins Family

Graduates of Harvard originating from Salem.
From NEGHR Vol. 5 - misc. Pynchon information.