John Winter of Gloucestershire is sometimes shown as being the same person as John Winter who immigrated to Massachusetts. It is possible that this association is true, but to date no proof has been found to support such an association.
The will of John Winter who died in Massachusetts clearly indicates that John Winter originated in England. A tradition has grown up that he was a member of a family in Gloucestershire. The tradition, however, is not proved.
Born England, about 1572. 
He was born about 1574. Also found Born 1574 
"From a genealogical perspective, London is an unsatisfyingly large place to be from, and I hope to eventually pin down a specific parish, when I have the time and/or money to do so. An on-line genealogy — for which I have been unable to find a source — claims our John was christened 23 Sept. 1565 in Attleborough, Norfolk. This certainly is at least plausible, as Attleborough and nearby Norwich were a primary source of early pilgrim migrants. (Attleboro, Mass., was named in honor of the Norfolk town.) It’s entirely possible our family may have originated in Attleborough but moved to London in the earlier 1500s. (But it equally likely this hometown could be wishful thinking; an earlier researcher may have found a John Winter born in the 1560s in a key Puritan community and leapt to the conclusion that he is ours. Without something more to go on, we may never know for sure.)
"Playing a large part in the decision to leave England was membership in “an intricate web of kinship, confraternity, and familiarity that not only connected those who traveled together in the same surge but also linked one surge to the next in a classic pattern of chain migration,” writes Thompson. This chain migration continued as we made our way west in America. This pattern also suggests that our Winter family was a part of the “puritan axis” that stretched from Norfolk down to London. But so far it hasn’t been possible to determine for certain where we originate within that area. 
"At Richmond Island off Cape Elizabeth, Robert Trelawny established a fishing and trading post in 1632, and for the next 10 years his son-in-law John Winter managed around 60 Devonshire fishermen working on three-year contracts, along with several farmers, swineherds, traders, artisans, and women domestics." []  No record, but probably in the time period 1630-1634, at which time he would have been aged 58-62., Probably accompanied by his son John, b. 1596, who would have been aged 34-38.
He was in Watertown, Mass. by 1636, a tanner and a proprietor of the town. 
Charles Pope's account gives an immigration date of 1638, however, this occurs after several significant events when John Winter, Jr. and his father were already here. 
We know nothing of John Winter’s wife or wives. It is likely that the three children who were in England in 1662 were by a first wife and that John (2) Winter, probably born shortly before John (1) Winter came to America, was by a second wife. John (1) Winter’s will mentions no wife.
We know nothing of John Winter’s wife or wives. John Winter's 1662 will identifies three of his four children who were in England at the time his will was written, had presumably remained there during the 26 years Winter had already been in Massachusetts, were living when John Winter crossed the Atlantic, and had therefore presumably been born there.
If John Winter crossed the Atlantic in 1636, assume then that the three children who remained in England were born in 1635, 1633, and 1631, with a marraige in 1630; or if John Winter Jr was two years old when he accompanied his father in 1636, assume his older siblings were born in 1632, 1630, and 1628, with a marriage in 1627.
John Winter was aged 90 when he died in 1662, thus born in 1572, and he would have been 55 in 1627.
Another theory would be that the 3 English siblings remained behind because they were already adults. Estimating from the other direction, if John Winter married in 1593 when he was 21, and had thse three childen in 1594, 1596, and 1598, they would have been aged 42, 40, and 38 in 1636, and quite firmly settled in London.
Stuart Bloom believes that the first children mentioned in 1662 were by a first wife and that his son John Winter, probably born shortly before John Winter, Sr. came to America, was by a second wife. 
None of this answers the question of what circumstances led John Winter, aged 64 in 1636, to cross the Atlantic with a two-year old son in tow, with or without an unnamed mother for the son.
Since John Winter’s will mentions no wife., it may be assumed that his wife had predeceased him, whether his first wife or second.
Another source -- documentation not found -- notes that on April 14, 1632 John Winter married Hannah Harrington in Cambridge, Massachusetts. Probably, however, John Winter was not in Massachusetts at that time, and references to a Hannah Harrington in that time period have not been found.
Speculation by Jack Day, April 25, 2015.
He was in Watertown, Mass. by 1636, a tanner and a proprietor of the town. 
"Watertown was one of the first six settlements in Massachusetts. The Watertown Covenant of 1630 is considered one of the founding documents of American democracy. We owe much of our genealogical and historical knowledge of the place to the excellent records that were preserved there from the earliest days. The strength of these records attracted the notice of historian Roger Thompson, a professor emeritus from the University of East Anglia, England. His book “Divided We Stand: Watertown, Massachusetts 1630-1680” provides an incredible portrait of life in our family’s first American hometown.
"Thompson identifies three surges of early Watertown settlement: one in 1630, a second from 1634 to 1636 and a third in 1637. The immigrants were predominantly from Essex, Suffolk and Norfolk in eastern England, the area called East Anglia, so named because it was the kingdom of the East Angles in the Anglo-Saxon era that began about the year 450. Essex is now part of the Greater London area, while Suffolk and Norfolk (homes respectively of the Angle South Folk and North Folk) are just north of London along the coast. All were a hotbed of Puritanism, with much marriage and moving to and fro within the area. 
"According to some earlier researchers, John Winter was in the second surge of migration to Watertown, perhaps arriving as early as 1633, while other sources give slightly later dates. (The 1633 date is mentioned in “Descendants of Nicholas Cady of Watertown, Mass. 1645-1910,” by Orrin Peer Allen, 1910. The Cadys are shoestring relations of ours.) (A possibility some researchers have seized upon is that he may have first settled in Scituate on Cape Cod Bay just south of Boston before moving to Watertown, about 36 miles away. This could mean John immigrated from England in 1633 or earlier but didn’t take up residence in Watertown until a few years later. However, this option looks very unlikely to me, as there was another man named John Winter who settled and definitely stayed in Scituate, where he was found murdered in 1651.)
He was proprietor at Watertown MA., 1636. Watertown was one of the first six settlements in Massachusetts. The Watertown Covenant of 1630 is considered one of the founding documents of American democracy.
"It is certain that our John Winter became one of Watertown’s earliest “proprietors,” a legal classification given to permanent citizens who were members of the church, and therefor eligible for shares in land grants from the township’s original 23,456 acres. Thompson makes a persuasive argument that these land grants were often made on the basis of insider connections, with some families getting far more than others. In a footnote, he says John Winter was among those who habitually appear to have received smaller shares, an observation validated by my examination of early land records. He was in on several land grants, but never very much acreage.
1636-7 Watertown, Massachusetts Bay Colony: tanner, proprieter. 
"There were three tanners in Watertown’s founding generation, of which John Winter’s operation was the smallest. Our ancestor, like most settlers, undoubtedly was also a small-time farmer. Tanners were in general regarded as important parts of the colonial economy, producing an essential commodity. Thompson notes that “Tanners in England were often associated with religious and political dissent,” perhaps partly explaining John’s decision to migrate. “It is unusual,” Thompson writes, “to be able to recover individual motives for emigration. We know from English church records that some Watertown settlers had been involved in religious protests prior to embarkation.”
"He is first mentioned in a July 1636 document listing the townsmen of Watertown, called Pigsguesset by the Indians, at which time he was granted 20 acres in what would much later become part of greater Boston. It is interesting to note that many Massachusetts Indian tribes were devastated by disease in the years immediately before our family’s arrival, probably from European germs brought over by cod fishermen or French explorers. In places, settlers found deserted fields ready for crops.
“Watertown,” one observer wrote, “is situated upon one of the branches of the Charles River, a fruitful plot, and of large extent, watered by many springs and rivulets running like veins throughout her body; which hath caused her inhabitants to scatter in such a manner, that their Sunday assemblies prove very thin.”
Lived Cambridge Farms. 
"The great 1855 genealogical history of Watertown by Philadelphia doctor Henry Bond includes this reference:
"John Winter died at Watertown 14 or 21 April 1662, age about 90. His will, dated 4 March 1661-2, proved June 1662, mentions no wife but refers to sons Richard and Thomas, late of London; daughter Alice Lachman of London, and son John, of Watertown, named his executor, and to whom he gave his lands and other goods in Watertown. The inventory of the estate, dated 13 May 1662, totaled pounds £104. 4. 6.
"By the standards of the time, an estate of £104 was a modest amount. Some first-generation migrants managed to amass more than £600. But it appears likely that John’s fortune had perhaps been diminished by early-day “estate planning,” being transferred during his life to his son John, who died in 1690 with a decent-sized fortune of nearly £360.
"It is discouraging that John Winter Sr. made no reference to his wife or wives in his will or elsewhere. It has been said by some genealogists that his presumably second wife was Hannah Harrington, born about 1600 in the county of Somerset, England. There were Harringtons among the first generation in the Boston area, but I personally haven’t come across any firm marriage record or other official link to the Winter family.
"Our immigrant ancestor’s life must have been an amazing adventure. Thompson’s Watertown book and other writings by him and others make it clear that the first generation was a much more complicated and interesting group than we were taught in grade school. Though they could be quite rigid in some of their beliefs, they also had strong traditions of charity and forgiveness. Judging by surviving records, John led a quiet and law-abiding life, setting the stage for our lives today.
John Winter made his will on 4 Mar 1661/62. He mentions his sons Richard and Thomas, late of London; his daughter, Alice Lachman, of London; and his son John of Watertown. 
John Winter died on April 14, 1662, in Watertown, Middlesex, Massachusetts, aged 90.
His inventory, taken on 13 May 1662, totaled £104.4s.6d. 
His will was proved on 16 Jun 1662. 
Will was made 4 Mar 1661-2 and proved June 16, 1662 at Watertown
John Winter made his will on 4 Mar 1661/62. He mentions his sons Richard and Thomas, late of London; his daughter, Alice Lachman, of London; and his son John of Watertown. John Winter died on April 14, 1662 in Watertown, aged 90.
He died April 14 or 21, 1662 at age abt. 90 in Watertown 
His inventory, taken on 13 May 1662, totaled £104.4s.6d.5 
His will was proved on 16 Jun 1662. 
The Will of John Winter, of Camb. Farms, dated Dec. 12, 1690, proved May 1, 1691, mentions no wife, but sons John (the eldest), Thomas, Samuel and drs. Sarah, Hannah, and Mary. 
John Winter was the father of the following children by an unknown wife or wives:
http://www.earlvillepost.com/stubloom/Fam_Winter.pdf. Accessed April 25, 2015
"Ancestry of Mary Blanchard Cutter" Gladden records of Mrs. Christofferson correspondences
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