The Family of Winn


No name is better known in Middlesex County, Massachusetts, or has been longer before the public, than that of Winn.  Its members have filled military and civil offices from the first settlement.  One was the first-born child recorded in Woburn, and to him was given the significant name of Increase.  From a family, which had contributed to Woburn, many of its most prominent and influential citizens came the donors in later years of the magnificent Woburn Public Library-Jonathan Bowers Winn and his son, Charles Bowers Winn, both now deceased.

From a remote period the Wynn, Wynne and Winn families were located in Wales.  The family abroad has been most prominently represented by Sir Watkin Williams Wynn, of Wynnstay, Denbighshire, whose lineage is ancient and noble.  Edward Winn, the progenitor of the Woburn family, it has been conjectured, was born in Wales, but more likely a native of England, related possibly to the Converses, Johnson’s, and other early Woburn families since of late years many of these relationships of early English immigrants been incontrovertibly established.

(1) Edward Winn came evidently, from England to America, bringing his wife Joanna, and children Ann, Elizabeth and Joseph.  He settled first in Charlestown, Massachusetts, and was one of the commissioners for founding the contemplated town of Woburn.  He one of the signers of the "town orders," or by-laws, for Woburn in 1640, one of the original planters of that town in 1641, and was taxed in the first tax rate of Woburn, 1645.  He was also the father of the firstborn child.  He was made freeman 1643, and selectman 1669.  His will was made at Watertown, May 6, 1682, and he died September 5, 1682.  His residence was near a place in Woburn, known as the Vineyard, at which was a watering-place (on present Park street), the house being on some spot near Middlesex, Chestnut and Kilby streets.  His wife Joanna died in Woburn, March 8, 1649.  He married (second), August 10, 1649, Sarah Beal, died in Woburn, March 15, 1680.  He married (third) Ann or Hannah Wood, respectively the wife of William Page, of Watertown; Nicholas Wood, of Medfield; and Edward Winn of Woburn.  She died before November 1, 1686. 

Children: 1. Ann, married, September 26.1648, Moses Cleveland (ancestor of ex-President Grover Cleveland). 2. Elizabeth married, May 21, 1649, George Polly. 3. Joseph, see forward. 4. Increase, born December 5, 1641, died December 14, 1690.

(II) Joseph Winn, son of Edward Winn (1), probably born in England, was a soldier in King Phillip's war, 1676, and an ensign in Phipps' Canada expedition to Quebec, 1690. His company was commanded by Captain Ebenezer Prout, of Concord (in the Middlesex county regiment, commanded by Major Nathaniel Wade, of Medford), the lieutenant of his company being Nathaniel Barsham, of Watertown, and the ensign Joseph Winn, of Woburn.  He died February 22, 1714-15.  He married Rebecca, born at Brookline, died I734, daughter of William and Mabel Reed, of Woburn. 

Children: 1.  Rebecca, born May 25, 1665, died April 6, 1679. 2. Sarah, born November 9, 1666, married, April 13, 1691, Ebenezer Johnson, of Woburn.  3. Timothy died March 22, 1677-78. 4. Abigail, born June 18, 1670, died June 25, 1670. 5. Joseph, born May I5, 1671. 6. Josiah, born March 15. 1673-74. 7. Joanna married, July 13, 1699, Edward Knight, of Woburn.  8. Rebecca (twin), born February 14 1679-80, married March 5, 1699-1700, Timothy Spaulding, of Chelmsford. 9. Hannah (twin), born February 14, 1679-80. 10. Abigail married John Rogers, of Billerica. 11. Anne, born November 1, 1684, died September 13, 1686.  12. Timothy, born February 27, 1686-87, see forward.

(III) Timothy Winn, son of Joseph Winn (2), born at Woburn, February 27, 1686-87, married Elizabeth, died May 14, 1724, daughter of John and Mary (Bruce-Cranston) Brooks, of Woburn.  He married (second), February 18, 1729-30, Jane, born November 4, 1699, died May 1775, of small-pox was the daughter of Thomas and Jane (Cheney) Belknap, of Woburn.  He received a deed of his father's homestead, August 5, 1709.  He died in Woburn, January 5, 1752.  

Children: 1.  Timothy, born July 5, 17I2, died March 3, I800. 2. Elizabeth, born September 1, 1719, married, December 7, 1742, Nehemiah Wyman.  3. Ruth, born August 6, 1732, married Samuel Reed, Jr.  4. Joseph, born July 3, 1734, see forward.  5. Jerusha, born August 4, 1740, married, September, 27, 1774, John Burnham.

(IV) Lieutenant Joseph Winn, son of Timothy Winn (3), was born at Woburn (Second Parish), July 3, 1734.  He married, October 16, 1760, Betsey, born August 18, 1742, died October 21, 18I7, daughter of Captain Timothy and Elizabeth (Goodwin) Pool, of Lynnfield.  He resided on his father's farm; enlisted in the French war, 1755; served at Lexington, in the battle of April 19, 1775; was ensign, First Company of Woburn militia, April 30, I775; was lieutenant in Captain Cadwallader Ford's company before April 1778, for three months.  Nine Woburn men under his command, who were engaged September 6, I778, to serve at Rhode Island, were ordered afterwards to Boston, for three and one-half months, ending January 1, 1779.  He was called lieutenant from I776 in tax lists.  He was a selectman of Woburn several years, and chairman of the first board of selectmen of the town of Burlington.  He was a member of the First Baptist Church in Woburn.  He died in Burlington, April 30, 18l7. 

Children:  1. Joseph, born September 29, 1761.    2. Timothy, born August 12, 1763, died January 10, 1803.   3. John, born December 20, 1765. 4. Abel, born December 9, 1767, see forward. 5. Betsey, born March 15, 1770, died November 16, 1828. 6. Susanna, born November 2, 1771, married, May 13, 1817, John Stearns, of Billerica at Burlington. 7. Benjamin, born April 9, 1774. 8. Sarah, born June 10, 1776, married, April 28, 1796, Ebenezer Tay, of Salem; married (second) Jesse Converse. 9. Pamela, born January 7, 1778, married, March 8, 1814, Gideon Foster. 10. Jerusha, born January 25, 1780, married, December 22, 1799, Benjamin Tay, of Salem. 11.  Lucy, born January 22, 1782, died October 18, 1833. 12. Olive, born December 6, 1784, married, April 28, 1805, Moses Billings Walker, of Charlestown at Burlington.

(V) Abel Winn, son of Lieutenant Joseph Winn (4), was born at Woburn (Second Parish), December 9, 1767.  He married, July 29, 1795, Ruth, born November 3, 1771, died January 24, 1848, daughter of Bartholomew and Sarah (Converse) Richardson, of Woburn.  He died in Burlington, October 12, 1847.  He was a farmer and resided on the farm he inherited from his father.  He was a magistrate, and a man of thrift. 

Children: 1. Ruth, born February 22, 1796, married, January 4, 1816, Samuel Abbott, of Woburn at Burlington. 2. Betsey, born February 22, 1798, married Augustus Roundy, of Beverly on March 8, 1851.  3. Abel, born September 2, 1800, see forward. 4. Joseph, born August 22, 1806, married Almira Shed, of Burlington. 5. Mary, born June 28, 1809, married May 4, 1828, Timothy Newhall, of Woburn.  6. George, born November 12, 1811, married, December 10, 1844, Maria Parker, of Woburn.

(VI) Abel Winn, son of Abel Winn (5), was born at Burlington, September 2, 1800.  He married, April 19, 1827, Lydia Stearns, born May 9, 1803, died December 9, 1868, daughter of John and Ruth (Cummings) Lovering, of Woburn.  He died May 9, 1868. He resided on his father's place in Burlington, attended the Baptist church of Woburn, was a Democrat in politics and later a Republican.  He was a private in the early militia.  One child, John, born July 3, 1828, see forward.

(VII) John Winn, son of Abel Winn (6), was born at Burlington, July 3, 1828, and died February 17, 1907.  He attended the common schools of Burlington and the Warren Academy of Woburn until eighteen, helping his father on the farm in the meanwhile.  When twenty years old he started a milk route, and continued in that line for three years.  Subsequently for ten years he carried produce into Boston.  In 1858 his father gave up business, and John Winn started farming on his own account.  He hired the farm and raised produce, and by general farming and large herds of cattle has carried on successfully the affairs of the place to the present day.  On the death of his father the entire property became his; it was a notable fact that a warranty deed bad never in the occupation of the Winn family been given on the farm.  The original tract comprised forty acres, which he increased to three or four hundred.  These lands are situated on the town line between Burlington and Woburn.  Mr. Winn was still active in farming and business at his death.  He bought and sold real estate in and around Woburn for himself and others and owned much realty and residential property in Woburn and Cambridge.  He built, a few years since, an elegant residence on the Woburn side of his farm for the occupancy of one of his sons. 

Mr. Winn was a Unitarian in religious belief, and a Republican in politics.  He had been a delegate to state, county and councilor conventions; was a member of the legislature in 1878, and there served on the committee of agriculture, being elected again in 1895 to represent in the house the towns of Burlington, Lexington, Bedford and Billerica, and he served on the committee on drainage.  The only town office he ever held was that of '”field driver." He was vice-president and director of the Woburn Five Cents Saving Bank, and served on the investment committee of that bank for fifteen years.  He was elected a member of the board of trustees, October 4, 1880 and vice-president, July 3, 1896.  He was also one of the board of directors of the Winning Home Farm, a charitable institution for children of Boston.

Mr. Winn married, 1851, Martha L. Baldwin, born May, 6, 1830, died October 11, 1852, daughter of Jonathan and Betsey (Parker) Baldwin, of Woburn.  He married (second), November 30, 1854, Martha Williams Garrison, born August 26, 1832, daughter of John Stanley and Sarah Ann (Cosman) Garrison, of Perry, New York. 

Child of John and Martha L. (Baldwin) Winn: Marah Baldwin, born June 12, 1852, married, October 4, 1886, Frank Murray, Pushee, of Thetford, Vermont.  Resides in Woburn.  The have Harold Baldwin. born January 16, 1890. 

Children of John and Martha Williams (Garrison) Winn: 1. George Edward, born April 13, 1856, see forward. 2. Joseph Franklin, born December 22, 1857, see forward.  3. Helen Louise, born October 27, 1860, married, August 30, 1890, Charles Willard.  One child, Winn, born May 14, 1891.  4. Marcia, born September 21, 1864.   5. John Garrison, born November 11, 1866, see forward. 6. Abbie Maria, born October 6. 1871.  Mr. and Mrs. Winn celebrated their golden wedding November 30, 1904.

Colonial Mansion - In the Winn Family for two hundred and sixty years - 

By the death of John Winn, a lineal descendant of one of the early settlers of the town of Woburn, forcibly, brings to mind the old Colonial mansion in which he was born, lived and died; and in which many of his ancestors lived and prospered, and where all of his children first saw the light of day.  It is a house rich in historical lore, and if its walls could but speak, what thrilling tales it could unfold.




In the Public Library is the fragment of a deed acknowledged 1709, whereby Joseph Winn, Senior, "for the love he bore his son Timothy Winn," granted to that son his homestead, consisting of one dwelling house, barn, corn house and other outhouses, with the land in the field before the dwelling house, the Billerica road parting this part of his homestead from the other part, whereon the house standeth, in other words, going between the two parts.  Other lands were also transferred, allowing, however, that his now "married wife" have the use of the house and barn on the homestead during her life, but after her death the son Timothy was to have full possession.

The son Timothy Winn died intestate in 1752 and the court assigned to the two sons; Timothy and Joseph, two-thirds of the real estate.  Through this son Joseph the homestead then passed to his son Abel, then to his son Abel, who was the father of John Winn.

It will thus be seen that the old homestead has been in continuous possession of the family for a period of two hundred and sixty years at least and perhaps much longer than that.

The house now standing is the original building on the original spot where it was first erected, although it has at various times been enlarged and improved.

Such a house, under whose roof tree so many men and women in long succession have been born, lived and died, is exceedingly fruitful in romance, reminiscence and suggestive thought of what has gone before.

The old hand-hewn timbers are many of them in plain sight; the open fire-place-and oaken projecting beams in the chambers are mute yet eloquent witnesses to the age of the venerable structure now among the few early ones yet remaining.  It is a typical home of the early colonists, with the stately ash trees guarding the front entrance, and in conjuring up the past, it is quite easy to picture in the mind the four-in-hand stage coach driving tip to the door to obtain refreshments for man and beast, for in those days this house being located on the direct road to Billerica, Groton and thence to Canada, was a tavern, pure and simple, and a design for the sign hung out at this hostelry is still in possession in the Library and from it a portion of the Winn so-called coat-of-arms was probably taken.

This house was known the country round as the "three broiled chickens," from a portion of the design on the sign.

In this old mansion are many relics of the past, old pewter ware, ancient china, solid mahogany four-posted bedsteads, surmounted by the richly carved pineapples from the solid wood.  Hanging above the mantle in the dining room is the old Queen's arm flintlock musket carried in the Revolutionary war by Lieutenant Joseph Winn, great-grandfather of the deceased John Winn.

The old brick oven of our grandfathers' days is another prominent feature of this time-honored home.

It is extremely, doubtful if another house as old as this can be found in the country, in as good a state of preservation and containing all the modern improvements.

(VIII) George Edward Winn, son of John (7), was born at Burlington, Massachusetts, April 13, 1856.  He was educated in the common schools of Burlington until twelve years of age, supplemented by a course in the Woburn public schools until eighteen, when lie pursued a course at Sawyer's Commercial College at Boston.  From early life he assisted in the work of the farm, and for a year or two after completing his education he continued this, shortly afterward engaging in the milk business for his father, which line of work he followed for twelve years.  He then decided to engage in business on his own account, and subsequently ventured for himself, beginning with two customers, and at the present time (1908) his customers number between seven and eight hundred of the best citizens of Woburn.  He has an extensive creamery on his place, and he purchases his milk stock from his brother, John G. Winn.  He resides in his beautiful residence at 236 Winn Street, just over the Woburn line in Burlington.  His time is devoted exclusively, to his business and his home.  He is an attendant of the First Congregational Church (Orthodox) of Woburn.  He casts his vote for the candidates of the Republican Party.  George E. Winn married, June 17, 1896, Alice Laura Bond, born February 5, 1864, at Thetford, Vermont, daughter of Chester Freeman and Persis Wilson (Dewey) Bond, of Thetford, Vermont.  No issue.

(VIII) Joseph Franklin Winn, son of John Winn (7), was born at Burlington, Massachusetts, December 22, 1857.  He received his education in the common schools of Burlington and Woburn, and graduated from the grammar school when seventeen.  He early began to help on the farm, and after schooling entered the milk business, for his father first, later for himself.  This he continued until 1902, his product having been sold mostly in Woburn.  In 1898 he entered into the sale of coal at Winchester, just beyond the Woburn line.  He conducts an extensive trade in Woburn and Winchester, with offices in both places, his yards being in Winchester.  He resides on his fifty-acre farm on Wyman Street, just in the edge of Burlington, formerly known as the old Kendall farm.  Mr. Winn is also engaged during the season in market gardening.  He is a Unitarian in religion, and a Republican in politics, having served his party as delegate to various conventions, and at present is on the Republican town committee for Burlington.  He is a member of Towanda Club, a social organization of Woburn.  Joseph F. Winn married (first), August 3, 1887, Mary Ella, born 0ctober 19, 1857, daughter of Augustus W. and Ellen (Montgomery) Jeffers, of Woburn, Massachusetts, the former of whom was a currier. 

Children: Martha, died young.  Madeline Jeffers, born November 30, 1890.  He married (second), March 29, 1900, Mary Ellen Briggs, born May 1, 1852, daughter of John and Mary Ann (Jeffers) Briggs, of Woburn. John Briggs was a shoemaker and civil war veteran.

(VIII) John Garrison Winn, son of John Winn (7), was born at Burlington, Massachusetts, November11, 1866.  He was educated in the Burlington district schools until seventeen, and then pursued a one-year course in the high school, and subsequently, after assisting his father on the farm, completed a three-term course in Bryant & Stratton's Commercial College at Boston.  He continued at market gardening and milk raising with his father until April 1898, when he purchased his present farm in the southeastern part of Burlington, consisting of forty-five acres, known as the old Walker place.  Mr. Winn is a successful market gardener and milk producer, supplying the Boston market and local trade, also supplying his brother, George E. Winn.  He has a fine herd of twenty head, mostly Holstein.  The homestead is one of the oldest in the town, having been built in 1744, this being the original building.  He is a Unitarian in religion, and a Republican in politics.  John G. Winn married, April 21, I898, Margaret Jessie, born in Garden of Eden, Pictou county, Nova Scotia, May 10, 1875, daughter of Roderick and Mary Ann (Cummings) Campbell.  One child, Martha Campbell, born January 14, 1904.

(For first generation see preceding sketch)

(II) Sergeant Increase Winn, son of Edward Winn (1), was born in Woburn, December 5, 1641, the first white child born in that town.  He was a sergeant in the company of Captain Thomas Brattle, of Boston, in King Philip's war, August 21, 1676, et seq. He was a prominent citizen of Woburn and selectman 1687-8. He married, at Woburn, July 13, 1665, Hannah Sawtelle, who was born in Watertown, Massachusetts, December 10, 1642, and died at Woburn, February 18, 1722-3, daughter of Richard and Elizabeth Sawtelle.  He died December 14, 1690.  

Children, born at Woburn: 1. Hannah, born April 11, 1666, married Samuel Baker. 2. Edward, born June 15, 1668. 3. Mary, born May 1 1670, died 1756; married Nathaniel Wyman, and second John Locke. 4. Sarah, born December 23, 1672; married Peter Fowle. 5. Abigail, January 8, 1678. 6. Rebecca, November 5, 1679. 7. Jacob, October 4, 1681; mentioned below. 8. Joanna, June 24, 1683. 9. Increase, February 9, 1685.

(III) Jacob Winn, son of Increase Winn (2), was born in Woburn, October 4, 1681; married first, June 28, 1704, Prudence Wyman, born at Woburn, December 26, 1683, daughter of William, and granddaughter of Francis Wyman, of Woburn.  William Wyman married Prudence Putnam, daughter of Thomas, and granddaughter of John Putnam, of Salem.  Thomas Putnam's wife was Ann Holyoke.  Winn married second, July 14, 1737, Phebe Palfrey. 

Children of first wife: 1. Prudence, born July 28, 1705. 2. Elizabeth, born September 29, 1707, married December 25, 1733, Andrew Richardson.  3. Hannah, born March 1, 1711. 4. Increase, born January 24, 1716-7; married Elizabeth Knight. 5. Joshua, born April 4, 1719; mentioned below. 6. Abigail, born January 25, 1722-3, married Mary Haseltine, of Bradford.

(IV) Joshua Winn, son of Jacob Winn (3) was born April 4, 1719; married about October, I745.

Children, born at Woburn: 1. Joshua, born May 17, 1747.  2. Jeremiah, April 29, 1749: mentioned below.  3. Molly, April 5, 1751. 4. James, April 7, 1753. 5. Jonathan, October 18, 1755.

(V) Jeremiah Winn, son of Joshua Winn (4), was born in Woburn, April 29, 1749.  He was a soldier in the Revolution, in Captain Pettingill's company, in August 1775, Colonel Loammi Baldwin's regiment.  He settled in Burlington, Massachusetts.  He married first, Mehitable Buck, of Wilmington, Massachusetts, and second, Rebecca Johnson, of Burlington. 

Children: 1. Jeremiah, born April 2, 1776; married Elizabeth Richardson, October 30, 1797.  2. James, born April 12, 1778; mentioned below. 3. Moses, born March 17, 1780; married first, Sally Johnson, born September 2, 1784, daughter of John and Achsah (Simonds) Johnson; married second, Fanny (Damon) Nichols, born January 11, 1780. 4: Francis, born June 8, 1782; married Eliza Jackson. 5. Sally, born July 22, 1788. 6. Sewell, born July 19, 1789; married Lydia Whittemore. 7. Mary, born October 17, 1790, married Ebenezer Hartshorn 8. Mehitable, born March 3, 1793; married first, John Dean; second, April 17, 1816, Benjamin Stevens. 9. Abigail, born December 28, 1797; married Jeremiah Bryant.

(VI) James Winn, son of Jeremiah Winn (5), was born in Burlington, April 12, 1778, and died September 11, 1832, at West Cambridge.  He was educated in the district schools and reared on his father's farm.  When he left home he bought a small farm in the southern part of Burlington, near Cummingsville, West Woburn.  In later years he became a chronic invalid and was a great sufferer.  He was baptized in the Congregational church October 27, 1805, and later was a member of the Baptist church.  He and his wife owned the covenant in the precinct church (Congregational) October 27, 1805. In politics he was a Democrat.  He served in the militia in his younger days.  He married, September 11, 1804, Sally Frost, born September 11, 1782. died September 17, 1855, daughter of Seth and Sarah (Hill) Frost, granddaughter of Samuel Frost, son of Ephraim, (see Frost). 

Children: 1. James, born January 31, 180_, baptized February 28, 1808; died January 10, 1860; married May 19, 1836, Hannah Converse, of West Cambridge, who died March 30, 1888 - 

Children: i. Jane, born March 24, 1837; ii.  Louise, born July 1, 1839; iii.  James, born July 25, 1841, married April 9, 1891, Mary Turnbull, iv.  Harriet A., born October 31, 1843, married October 5, 1870, Stratton Penstone; v. Rebecca, born October 11, 1845, died March 14, 1846; vi.  Charles G., born December 11, 1847, married July 27, 1896, Lora.

Source:  Historic Homes and Places and Genealogical and Personal Memoirs relating to the Families of Middlesex County, Massachusetts - W.R. Cutter -  Volume III, pp. 1139-1143.

My Thanks to Bonnye Hackett for providing this information!  

If you have any pictures of the early Winn family from Woburn,
email them to me and I will put them online here!

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