Holbrook line: Edward Winn, Immigrant -

Edward Winn should be fairly well documented.  After all, he's a direct ancestor of President Grover Cleveland, so shouldn't we expect to know more about him than about the average guy who came to America?  Well, we might expect it, and there is perhaps a little more information than we're used to finding, but the amount is still pretty minimal, and in some cases, conflicting. 

For instance, was he born in  in Ipswich, Suffolk, England in , or he was born in Thornton Curtis, Lincolnshire in.  I would be happier if I could find an exact birth or christening date.  I tend to think the Ipswich, Suffolk information could be a guess based on that being the point of his departure to Massachusetts, but at this point anything is possible.

He married Joanna, probably Joanna Sargent although I have seen it suggested that her name was Hatch) in England and they came to America with at least three of their children sometime before 1640.  There seems to be at least a hint that the family spent some time (weeks? months? years?) in Charlestown when they arrived here, and in 1640 Edward was one of several men who were asked to plan the settlement of Woburn, Massachusetts.  The family was there by 1641, and Edward was admitted a freeman there in 1643. 

After that, there is little that is on record.  The birth of his son Increase is recorded in 1641 as the first child born in Woburn.  He is listed in a deponent's index, and I'd love to read that deposition for it might tell his age, where he was from, his current occupation, and his statement about the case he is testifying in.  So far I haven't found the court records, though.  His wife Joanna died in 1649 and Edward married Sarah Beal that same year.  She also died, and he then married Anna or Hannah Page Wood, a widow.  There are three references to land owned by Edward Winn in a book of early land deeds, but the land, whatever its size, is described only as a boundary for someone else's land.  Also he was a town selectman from 1660-1664. 

He died in Woburn on September 5, 1682, having helped to found a town and in one way or another, having seen it through the first 40 plus years of life.  For that, he deserves to be honored. 

The line of descent is:

Edward Winn-Joanna probably Sargent
Ann Winn-Moses Cleveland
Enoch Cleveland-Elizabeth Counts
Sarah Cleveland-Israel Joslin
Sarah Joslin-Edward Fay
David Fay-Mary or Mercy Perrin
Luceba Fay-Libbeus Stanard
Hiram Stanard-Susan Eddy
Louis Stanard-Mary Alice Hetrick
Etta Stanard-Loren Holbrook
Gladys Holbrook-Richard Allen
Their descendants

Holbrook line: Moses Cleveland 1620-1703, Immigrant

There is more information about Moses Cleveland than is sometimes available,because he left more records than some immigrants, and because he is the ancestor of Grover Cleveland and thus has been pretty thoroughly researched.  Still, I haven't seen documentation for his birth and there are varying guesses as to his parents. 

My favorite candidate for his parents would be Isaac Cleveland and Alice, last name unknown.  They were in Ipswich, Suffolk, England, which is generally given as Moses' birthplace, and they were of the right age to be his parents. In addition, there is the Biblical name tradition, as it appears.  Other suggestions I have seen were for a Samuel Cleveland, but I don't think he was from Ipswich.

There is an absolutely fascinating story about Moses's voyage to America, but it may well be just that-a story.  Still, on the off chance that it's correct, the story goes that when Moses came to America, he had thought it would be Virginia rather than New England.  The story goes that when they landed at Jamestown, the group after a short time decided there was too much trouble with the native Americans, and boarded the ship to go to Massachusetts instead.  There is much that is suspicious about this story but it could have happened.

At any rate, young Moses, no more than fifteen, arrived at Plym.  outh or Boston in 1635.  He was a ship's carpenter apprentice when he arrived,  He seems to have stayed in Boston for about three years, then in 1638 he settled in Charlsetown. 

He was still serving a master, probably Edward Winn, when he went to Woburn in 1640 or 1641, but was admitted a freeman in 1643,  He was granted land in 1649, and on February 3,1648/1649 was appointed by a committee to lay out his own land.  He married Ann Winn, daughter of Edward Winn, in 1648 and the couple had at least eleven children.  The first is listed with a birthdate of 1651 so it's possible there were miscarriages or still born children in the early years of their marriage. 

Moses was a joiner, or basically a finish carpenter, and worked both on ships and on homes.  This gave him an income sufficient to support his large family.  He is listed on the militia roll in 1663.  A later listing for Moses Cleveland during King Philip's War is more likely his son Moses.  He became a tithing man for the church in 1680, so he was a Puritan.  He died in Woburn on January 8, 1702, having lived there for 60 or more years, and having survived his wife by about 20 years.  It isn't often that our ancestors stayed in one place for a long time so I would like to thank Moses for doing just that! 

The line of descent is:

Moses Cleveland-Ann Winn
Enoch Cleveland-Elizabeth Counts
Sarah Cleveland-Israel Joslin
Sarah Joslin-Edward Fay
David Fay-Mary or Mercy Perrin
Luceba or Euzebia Fay-Libbeus Stanard
Hiram Stanard-Susan Eddy
Louis Stanard-Mary Alice Hetrick
Etta Stanard-Loren Holbrook
Gladys Holbrook-Richard Allen
Their descendants

Holbrook line: Enoch Cleveland 1671-1729

Enoch Cleveland was of the first generation of New Englanders.  His father Moses Cleveland, had arrived probably at Boston in 1635, as a servant to his future father-in-law, Edward Winn.  Ann was just a young woman at the time, and perhaps Moses had to serve a period of indentureship, for Moses and Mary weren't married until 1648.  Enoch was the youngest son of this couple, one of 12 children, and the family lived in Woburn, Massachusetts. 

Enoch married Elizabeth Counts or Counce on  October 9, 1695 in Charlestown, Massachusetts, which was just outside of Charlestown and in fact may have been included in the Charlestown borders at one time.  Elizabeth was the daughter of Edward Counts/Counce and Sarah Adams, and was one of at least five children.

Enoch learned and practiced the trade of a tailor, so if he farmed it was only to support his family. Likely he had a few farm animals, if nothing else.  He and Elizabeth moved several times, from Charlestown to Sudbury to Framingham, then Acton, Marlborough, and finally Concord, in 1719.  His first wife died in 1719 and he may have married again, to Elizabeth Wright.  There are no known children from the second marriage, and just four children from the first marriage.  Sarah was the oldest, and then came Enoch, James, and Jonathan. It is hard to tell whether Enoch moved so much because of hard times, or because his trade was so much in demand.

Enoch has what looks to be an interesting probate record, case number 4616 in the probate court of Middlesex County, and perhaps more can be learned from that.  The images are available on americanancestors.org but I can't read them, and I haven't been able to find anyone who has posted the will or papers on line.  Apparently FamilySearch will be bringing the images online "soon", as there is a research page about the collection.  Maybe I'll have better luck reading them there.

Update:  I tried again to read the probate, and have been able to glean a little bit. Enoch died without a will, and his son Jonathan Cleveland was the administrator.  There is a document with Israel Joslin's signature on it.  There were several pages with numbers and lists.  At the end is what I think is an inventory.  I will have to wait for better glasses or/and a stronger magnifying glass to read more!

As far as I can tell, Enoch didn't have an involvement with the military, or at least it was only for local drills.  There is an Enoch Cleveland who served for about 7 1/2 months in 1725, as a corporal, but this is likely son Enoch, not our ancestor.

More research needs to be done, of course, not only to study his probate records but to determine whether he was a freeman or not, and to find what churches he would have supported.  I'd also like to know whether he was a hard-luck kind of guy or a respected citizen with a needed trade.  Someday perhaps I will find answers to these questions.

The line of descent is:

Enoch Cleveland-Elizabeth Counts
Sarah Cleveland-Israel Joslin
Sarah Joslin-Edward Fay
David Fay-Mercy Perrin
Euzebia Fay-Libbeus Stanard Jr.
Hiram Stanard-Susan Eddy
Louis Stanard-Mary Alice Hetrick
Etta Stanard-Loren Holbrook
Holbrook children, grand children, great grandchildren, and great great grandchildren