John Penny, eldest son of Roger , was b. in 1728 or 29 and bp. Jan. 11, 1730 at St. Nicholas, Deptford. He is first mentioned in the Dockyard records during the Lady quarter of 1746 as shipwright apprentice to Roger Penny . At that time he worked 75-1/2 days, 0 nights and 104 tides, earning £6, 6s, 0d. The total given with his father's earnings was £10, 19s, 6d. In 1747 John was again indicated to be a "servant" to Roger.
    n 1748 John was listed as "servant to the exec. (executor, his mother) of Roger Penny", and Sept. 1 he was "servant to the widow Penny" . His age at this time was given as 19-1/2 yrs, suggesting he was b. in Jan. or Feb. of 1729. Since he had 3 yrs 6 mos service at this time, he must have entered the Dockyard early in the year 1745. This conclusion is supported by an entry of Jan. 1, 1777, stating he entered (the Dockyard) Feb. 19, 1745. In 1748 his behavior was described as "well". In 1749, 50, and 51 he was again listed as "servant to the ex of Roger Penny".
    The parish registers of St. Paul's, Deptford, the "new church", show John Penny, "bachelor", m. Elizabeth Rout, "spinster", Sunday, Sept. 10, 1758, "by license". Both were of that parish. From the Marriage Licence and Bond, we found that Elizabeth was the daughter of Norbury Rout, Baker, of St. Paul's, Deptford. She was bp. at St. Nicholas, Deptford, on Dec. 29, 1739. Her parents were shown as living in Flagon Row.
    John and Elizabeth Penny's first child, Elizabeth, was bp, like all their children, at St. Paul's, Oct. 17, 1759. This was the year in which the British general James Wolfe captured Quebec City from the French. Baby Elizabeth was bur. in Oct., 1760 at the same church, the first year in the reign of King George III. A second daughter, Hannah, was bp. Feb. 13 or 23, 1761. One and one-half years later, a third daughter, Elizabeth Friend, was bp. Sept. 12, 1762; however, she d. as a child and was bur. June 20, 1764.
    John and Elizabeth's first son, John, was bp. Sunday, Nov. 11. 1764. The parish entry recording his bp. used the present spelling of 'Penney', although it is first seen in Dockyard records in 1747 and 48. A second son, William, bp. April 20, 1766, d. four years later and was bur. Sept. 3, 1770. Thomas, a third son, was bp. July 31, 1768 and July 15, 1770 a fourth daughter, Ann, was bp. Thus in twelve years of marriage, 3 of their 7 children had d. young. Apparently John and Elizabeth were especially fond of the
name William, since on April 20, 1772 they bp. a second child by that name. He is the one who carried on our Penney line. James Bravil was bp. March 15, 1774, but he d. 14 months later, May 23, 1775. Like the case with the two Williams, Aug. 15, 1776 a second child was bp. James. The last child to join John and Elizabeth's family was a third Elizabeth! She was b. Nov. 3, 1778 and bp. Dec. 7, 1778.
    John's name is found in the Dockyard records for 1755 and 1759. He took on an apprentice, Thomas Mason, during the first quarter of 1765. His own first son John was then still a baby. July 31st of that year he was promoted to quarterman. It was stated in 1765 that John Penny was age 35, 5' 5" tall, m. and from Deptford parish. In 1770 he was again listed as a quarterman shipwright, and training Thomas Mason. By 1775, his former apprentice having completed the required 7 years, John took on a second apprentice, George Slous. That same year the American Revolution began, including the battles of Lexington, Concord and Bunker Hill.
    Jan. 1, 1777 John still held the rank of quarterman. He was said to be 5' 6-1/2" tall (repeated again in 1779 &1784) and had 7 children. The Jan., 1779 record provides three other important pieces of information about John: He served 1 yr 6 mos at sea (stated again in 1784) although we don't know when, was of "dark" complexion and was of "good character". Deptford was given as his "abode". He now had a third apprentice, his eldest son John (II), age 16, who entered the Dockyard Sept. 28, 1778. In the first quarter of 1780 and in Sept. of 1782 John was still a quarterman and was described on the latter date as a "sober, honest, good man". He was 53 yrs of age in 1783, having put in 30 yrs 6 mos of service in the Yard as a journeyman shipwright. In 1784 he was said to have been of "first class character". As of the first quarter of 1785 his son John was still his apprentice, albeit nearly finished.
    As of 1790, John Penny, quarterman, was 60 yrs of age. His apprentice was now William, age 20, his third son. This is shown very clearly in the pay book for that year. William entered the Dockyard Oct. 3, 1785, being refused Dec. 27, 1784 for "not being of age". By 1794 William was a journeyman shipwright; however, in the third and fourth quarters of that year, his "wages (were) paid to (his) father John by order". The reason for this is unknown: it must have been an interesting story. As soon as William had completed his apprenticeship in 1792, James the fourth and youngest son was taken on for training by John. James entered the Dockyard Sept. 28, 1792. In 1795 and 96, James was continuing to train in the building of ships under his father's direction.
    By June 2, 1803 John Penny was pensioned off, leaving the service at the rank of foreman and 'leading man of shipwrights'. He received £24 per annum, £6 per quarter. Of the pensioners on the list at that time, shipwrights received £20 per annum, and laborers £10 per annum. He, with with two others got the highest rate. As a "superannuated artificer", he continued to collect his pension each quarter and sign his name each time in the accounts book in a very legible hand .
    In the summer of 1802 the First Lord of the Admiralty, St. Vincent, due to temporary peace, discharged rom the Dockyards over one-quarter of the men recruited during the wars with Revolutionary France. Old and infirm men were discharged or superannuated (retired) and he ordered that no men be hired in the future over 28 years of age. When war came once again, the maximum age was raised to 35 in 1803, and 45 in 1804. In 1805 the age limit was eliminated entirely.
    The following is John's Will written in 1807 (Prob. 11/1511). It and the Death Duty record are in the collection at the Public Record Office at Chancery Lane. The contents of both records prove illuminating indeed! As with Roger's Will, the copy below accurately reflects the original.

"John Penney In the name of God Amen. I John Penney shipwright of the parish of St. Pauls Deptford in the County of Kent being of sound mind and memory but weak in body and sensible that this mortal life must end and all worldly possessions must be given up so on this 28th day of October in the year of our Lord 1807 make this my last will and testament revoking all former wills, deeds and promises made at any time or times heretofore by me that is to say first I commend my soul into the hands of my maker who gards it and my body to the earth bequeath to my well beloved son James Penney shipwright of the aforesaid parish for divers causes hereunto moving me all and every of my goods and chatels and yearly estates that I may possess at my decease and I do hereby give and bequeath to the said James Penney aforesaid all my clothes, books, china, prints, plate, and household furniture, wearing apparel effects, monies  and pension that I may be possessed of or entitled to at or after my decease the profits rents and rents and profits that may arise from my four leasehold houses situated in Dowling Street Deptford in the County of Kent to be solely appropriated for this the aforesaid James Penneys use and for his use only during his natural life and after his decease then shall the said four household (leasehold?) houses be equally divided among the other three brothers and three sisters living but if not living after time of the decease of the said James Penney then to be equally divided among the survivors of the aforesaid brothers and sisters then living and I do hereby appoint for my lawful exec. and admin Mr. John Penney of King Street Deptford, Mr. Thomas Penney of Sheerness and Mr. William Penney of Bark (Back?) Lane Deptford to execute this my last will and testament executed on this 28th day of October the year above named. In witness whereof I have hereunto set my hand and sealed - John Penney - signed sealed, published and declared by the said John Penney as his last will and testament in the presence of us the subscribers - Benjamin Porter(?) - Richard Porter(?). Proved at London 18th April 1811 before the worshipful John Daubany Doctor of Laws and Surrogate by the oaths of John Penney and Thomas Penney the Sons and two of the executors to whom administration was granted having been first sworn duly to admin power reserved to William Penney the Son also another executor."

Some theories as to the origins of John Pinney that have been discussed
 
1. Riverhead History, by Virginia Wines shows John Penny and then gives us records of a ship captain in the 1650's and 1660's. Her presentation implies that they were the same person. It seems to me he could have been more likely a son or other relative of that captain, based on dates of wife, children, etc.

2. He could be a son of an earlier immigrant elsewhere in the colonies who moved to Long Island.

3. He could be the prisoner, "John Pinny", exported to Barbados from the Monmouth Rebellion, arrived in Barbadoes apparently sometime Oct-Jan 1685 (remember Jan 1685 follows Oct 1685 in the old calendar.) At first blush, this seems to blend well with the first signs of John Pinney in Southampton about 1685. Worthy of note is that there was another prisoner whose last name is given as Jasper Dyamond. A Thomas Diament / Diamont married a daughter of John Pinney.

Children of Joseph Penny and Deborah Squires were as follows:

         2. i. Deborah, born 21 Dec 1790; married John Edwards.
         3. ii. Capt. Joseph Jr, born 26 Aug 1791; married Harmony Squires.
         4. iii. Mary, married Jonathan Norton Robinson; born 25 Jun 1793.
         5. iv. Phebe, born 6 May 1795; married John Sawyer Foster.
         6. v. Harvey, born Jun 1797; married Abigail Raynor.
         7. vi. Hannah, born 24 Feb 1799; married Sylvester F. Terry.
         8. vii. Millie M., born 28 Apr 1801; married Benjamin Davis.
         9. viii. Nathan, born 22 Jan 1804; married Hannah Fournier.
         10. ix. Manassah, married Rosetta Goodale; married Phebe Robinson; born 1805.
         11. x. Austin, born 27 May 1807; married Sarah Ann Benjamin.
         xi. Esther A.; born May 1809;3 died 11 May 1885 at Flanders, Suffolk, NY; buried at  Fournier Cemetery, Red Creek., Suffolk, NY;   She never married. See Suffolk Probate File no. 10130(A).
         xii. Lodewick; born 13 Jul 1811; died 20 Oct 1819 at age 8; buried at Fournier Cemetery,  Red Creek, Suffolk, NY; AE 8 years, 3 months, 7 days.
         12. xiii. Frances, born 18 May 1814; married Oliver K. Buckley.

    2. Deborah Penny; born 21 Dec 1790; married John Edwards 21 Jan 1814; died 8 Jan 1877 at  age 86; buried at Oakland Cemetery, Sag Harbor, NY.

    Children of Deborah Penny and John Edwards were as follows:

         i. Deborah C.; married R. Topping.
         ii. Joseph A.; married Caroline Snooks.
         iii. Mary J.; married Henry Tuthill.
         iv. Lodowick H.; married Lucy Avory; buried at Oakland Cemetery, Sag Harbor, NY;  born 10 Mar 1821; died 3 Sep 1849 at age 28.
         v. Frances S.; married Atwater Hale.
         vi. Hannah; married William White.
         vii. Charlotte M.; married Samuel Polley.
         viii. John P.; married Sarah Hayes.
         ix. Austin; buried at Oakland Cemetery, Sag Harbor, NY born 1 Mar 1832; died 16   Mar 1832.
         x. Henrietta; buried at Oakland Cemetery, Sag Harbor, NY; married Charles C. Douglas.
    3. Capt. Joseph Penny Jr; born 26 Aug 1791; married Harmony Squires 1813; died 1 Nov 1859 at Greenport, Suffolk, NY, at age 68; buried at Webb St. Cem., Greenport, NY. He was a sea captain from Greenport, NY. See Suffolk probate file no. 5168.

    Children of Capt. Joseph Penny Jr and Harmony Squires were as follows:

         i. Hiram S.; born 1813; died 9 Jul 1840;8 buried at Webb St. Cemetery, Greenport, NY; He was lost at sea in 1840.
         ii. Miranda; born 3 Jun 1815;10 married Madison W. Young, son of Warren Youngs,  Sep 1839;11 died 31 Oct 1886 at age 71.
         iii. Capt. George Gilbert; born 21 Oct 1816 married Esther S. Havens 23 Jun 1840 at  Shelter Island, Suffolk, NY;13 died 28 Dec 1888 at Mattituck, Suffolk, NY, at age 72;  buried 1889 at Shelter Island, Suffolk, NY; He appeared on the census of 1850 at Southold, Suffolk, NY. He lived at Greenport,   Suffolk, NY.
         iv. Harmy H.; born 1822; died 13 Aug 1841; buried at Webb St. Cemetery, Greenport, Suffolk, NY;
         v. Maria L.; buried at Sterling Cem., Greenport, Suffolk, NY; born circa 1825; died 8  Feb 1834.
         vi. Manetta J.; married Leroy R. Westfall; buried at Webb St. Cem., Greenport, NY; born   1826;18 died 1896.
         vii. Capt Wickham H.; married Clara M. Woodhull; born circa 1828. He died in a foreign port.
         viii. Schuyler J.; born circa 1830; married Maria Virginia Ryder before 25 Mar 1857. He lived at Main Street near Amity, Greenport, Suffolk, NY.22 He Capt. Schuyler Penny's vessel foundered at sea. All on board were lost.
         ix. Elizabeth W.; born circa 1832; married Rev. William Wood Apr 1865.
         x. Deborah A.; born circa 1833; married Elisha Hallock 14 Jan 1857 at Greenport,  Suffolk, NY; died 1865.
         xi. Frances M.; buried at Webb St. Cem., Greenport, NY; born 1835; died 1896.
         xii. Capt. Horace W.; married Amelia Waterhouse; born 1836;24 died 19 Aug 1886; buried at Webb St. Cem., Greenport, NY;   He was knocked overboard by a jib boom and drowned.

    4. Mary Penny; married Jonathan Norton Robinson; born 25 Jun 1793; died 13 May 1888 at  Sabetha, Kansas, at age 94.

    Children of Mary Penny and Jonathan Norton Robinson were as follows:

         i. William; married Ruth Standard.
         ii. Norton F.; born 26 Dec 1830 at Southampton, Suffolk, NY; married Phebe R.  Penny, daughter of Harvey Penny and Abigail Raynor, 1857 at Southampton, Suffolk,  NY; died 1916 at Sabetha, Kansas.
         iii. Mary E.; married Costello C. Buck.
         iv. Theron; married Maria Standard
         v. Eugene.
         vi. Dwight.

    5. Phebe Penny; born 6 May 1795; married John Sawyer Foster, son of Wakeman Foster and  Martha Sawyer, 12 Dec 1812 at Pon Quogue, Southampton, NY;27 died 25 Oct 1881 at age  86.

    Children of Phebe Penny and John Sawyer Foster were as follows:

         i. Edward H.; born 20 Jan 1815; married Mary Bellows Dec 1840; died 1903.
         ii. Phebe Ann; born 1817; married Joshua Corwin 1835; died 1881
         iii. Mary Jane; born 1818 married Theodore Conklin 184 died 1889.
         iv. John Harvy; married Mary Jane Smith; born 1820; died 1905.
         v. Joseph L.; married Deborah A. Davis, daughter of Benjamin Davis and Millie M.  Penny, 1849 at Sag Harbor, Suffolk, NY.
         vi. William S.; born 14 Oct 1824; married Mary Ann Penny, daughter of Austin Penny  and Sarah Ann Benjamin, 19 Mar 1849 at Flanders, Suffolk, NY.
         vii. Deborah A.; married Sylvanus R. Jackson; married William Stratton; born 1825;  died 1904.
         viii. Nancy M.; born 1827; died 1887.
         ix. Nathan P.; born 1829; married Electra A. Wells 1851; died 1897.
         x. James R.; born 1832; married Sarah L. Phillips 1857 at Southampton, Suffolk, NY.
         xi. Emeline P.; born 1834; married Henry Frank Carter 1852 at East Quogue, Suffolk, NY; died 1886
         xii. Rosetta Matilda; born 2 Feb 1836 at Good Ground, Southampton, Suffolk, NY;  married Allen Parker Squires, son of Alvin Squires and Charry Lane, 10 May 1854 at  Riverhead, Suffolk, NY;17 died 10 Aug 1900 at Good Ground, Southampton, Suffolk, NY,  at age 64.
         xiii. Frances A.; born 1840 married Capt. William N. Raynor 1858 married Silas Topping 1874; died 1888.
         xiv. Alonzo Allen; born 15 Oct 1841; married Georgianna Anna Squires 15 Oct 1865

    6. Harvey Penny; born Jun 1797; married Abigail Raynor 19 Aug 1824; died 22 Feb 1865 at  age 67.

    Children of Harvey Penny and Abigail Raynor were as follows:

         i. Catherine R.; married Thomas P. Ripley; born 2 Jun 1826.
         ii. Phebe R.; born 1833;31 married Norton F. Robinson, son of Jonathan Norton Robinson and Mary Penny, 1857 at Southampton, Suffolk, NY;25 died 27 Aug 1908 at  Sabetha, Kansas.
         iii. Ann M.; married Joseph A. Williams; baptized 3 Sep 1830.
         iv. Frances M..
         v. George S.; born circa 1834
         vi. Mary J.; born Oct 1836;32 married William Bishop circa 12 Dec 1855.
         vii. Harriet A.; married A. Frank Trask; born circa 1841.
         viii. William R.; born circa 1850.

    7. Hannah Penny; born 24 Feb 1799;3 married Sylvester F. Terry 20 Jun 1823;3 died 18 Oct 1881 at age 82.

    Children of Hannah Penny and Sylvester F. Terry were as follows:

         i. Austin P.; married Emeline Ferry.
         ii. William N.; married Hannah Boulder.
         iii. Sylvester J.; married Pollie Sealy.
         iv. Joseph E.; married Mary E. Baylis.
         v. Hannah Ann; married Gilbert Horton.
         vi. Sylvester F..

    8. Millie M. Penny; born 28 Apr 1801;3 married Benjamin Davis 10 Apr 1827;3 died 13 Apr 1889 at age 88

    Children of Millie M. Penny and Benjamin Davis were as follows:

         i. Deborah A.; married Joseph L. Foster, son of John Sawyer Foster and Phebe Penny, 1849 at Sag Harbor, Suffolk, NY.
         ii. Benjamin F.; married Ruth L. Smith.
         iii. Mary R.; married Jacob Barren.
         iv. Betsy M.; married Oscar Goodale.
         v. Emily C.; married John A. Purdy.
         vi. Joseph L.; married Ellen A. Graham.
    9. Nathan Penny; born 22 Jan 1804; married Hannah Fournier, daughter of John Fournier died 6 Nov 1880 at age 76.  He claims (mistakenly?) that he "traces his ancestry back to one Joshua Penny, who located  here on his emigration from England, and during the war of 1812 participated in that conflict." This conflicts with: Wines, Pioneers of Riverhead Town. Also, see Suffolk probate file no.  9066.33

    Children of Nathan Penny and Hannah Fournier were as follows:

         i. Nathan N.; born circa 1829;34 married Hannah Jane Terry, daughter of Mitchell Terry and Fanny Sweezy, 20 Jul 1853.
         ii. Augustus S.; buried at Flanders Cemetery, Suffolk, NY;5 born 4 Oct 1831;36 died 8 Jul 1864 at age 32.
         iii. Cecelia A.; buried at Flanders Cemetery, Suffolk, NY;5 born 2 Mar 1833;17 died 25 Jan 1911 at age 77.
         iv. Oliver F.; born 16 Feb 1835;36 died 29 Jan 1862 at Chattanogua, Tenn, at age 26;  buried or memorial at Flanders Cemetery, Suffolk, NY. He served in Illinois Regiment in the Cival War and died in service at Chattanogua.
         v. Eleanor D.; married George Mitchell Terry, son of Mitchell Terry and Fanny Sweezy, Apr 1857.38
         vi. John F.; married Rose Benjamin; born 7 Apr 1839;17 died 30 Dec 1910 at age 71.
         vii. Emily T.; buried AE 34. at Flanders Cemetery, Suffolk, NY;5 born 6 Aug 1842;36 died 10 Nov 1876 at Flanders, Suffolk, NY, at age 34.
         viii. Robert W.; born 1 Dec 1844 at Flanders, Suffolk, NY;39 married Carrie L. Wells 22 Oct 1874;39 died 1921.
         ix. Hannah I.; married Jonas E. Smith; born circa 1848.

    10. Manassah Penny; married Phebe Robinson; married Rosetta Goodale; born 1805;3 died 1892 He removed to Illinois accompanied by his mother in 1858. He appeared on the census of 1860 at Andover, Henry, Illinois.

    Children of Manassah Penny and Rosetta Goodale were as follows:

         i. Elwyn; married Nancy J. Corwin.
         ii. (--?--); died 19 Apr 1835;5 buried at Red Creek Cem., Southport, NY. She has a Burial stone inscription in Red Creek Cemetery that gives identity only as 'Infant daughter' with only a date of death.
         iii. Gertrude; buried at Red Creek Cem., Southport, NY; AE 10 DAYS;5 born 16 Oct
         1845;5 died 16 Oct 1845.

    Children of Manassah Penny and Phebe Robinson were as follows:

         i. Frances; married Ithicar C. Converse.
         ii. Theodore; married Marcia A. Valentine; died between 1861 and 1865; the Civil War, fighting with the Union Army.
         iii. Norton; married Nellie Atwater.
         iv. Sarepta; married James Converse.
         v. Rosamond; married George S. Jackes.
         vi. Isabel; married Joseph Woods.
         vii. Warren; died between 1861 and 1865; fighting in the Civil War, fighting for the Union  Army.
         viii. Charles K.; married Rebecca Gardiner.

    11. Austin Penny; born 27 May 1807;3 married Sarah Ann Benjamin 19 Mar 1828;3 buried at  Good Ground Cemetery, Hampton Bays, NY;40 died 25 Feb 1890 at Good Ground, Southampton, Suffolk, NY, at age 82.3    He has probate records: Suffolk probate file no. 11464.

    Children of Austin Penny and Sarah Ann Benjamin were as follows:

         i. Mary Ann; born circa 1829;41 married William S. Foster, son of John Sawyer Foster and Phebe Penny, 19 Mar 1849 at Flanders, Suffolk, NY.
         ii. Gilbert Allen; born 30 Jul 1830;17 died 17 Oct 1924 at age 94.
         iii. Capt. Austin Everett; married Henrietta Townsend; married Mary Denison; born 2 Jun 1831 at Flanders, Suffolk, NY; married Maria Morton Tuthill 25 Dec 1852 at New Suffolk,  Suffolk, NY. He was a sea captain.
         iv. Charlotte M.; born 2 Jun 1831;17 died 2 Sep 1900 at age 69.
         v. Joseph N.; buried at Good Ground Cem, Hampton Bays, NY;40 born 16 May 1836 at  Flanders, Suffolk, NY;40 married Rachel Amelia Davison, daughter of John Kimball Davison and Mary Gaylord Burr, 4 Apr 1859 at Clinton Center, Wayne Co., PA;5 died 20 Feb 1911 at age 74.
         vi. Sarah E.; born circa 1850; married Leander Squires 9 Jan 1868 at Good Ground,
         Southampton, Suffolk, NY.   She Marriage at Good Ground Jan 9 1868 by Rev. C. Pike. Leander Squires to Miss  Libbie Penny, y. daughter of Austin Penny of PomQuogue. -Deaths taken from the  'Republican Watchman,' NYGBS Library, v.1 p.17.
         vii. Alanson C.; married Fannie H. Jackson; born circa 1853;20 died 13 Jan 1928.  He Suffolk probate file no. 29864.
         viii. Alexander H.; married Emeline A. Foster, daughter of Edward H. Foster and Mary Bellows, 28 Feb 1867 at Good Ground, Southampton, Suffolk, NY;14 died circa 1905.   He Alexander H. Penny, from Good Ground, served in the 6th Cavalry in the Civil War. He returned from service. -Munsell, Pub., History of Suffolk Co., NY., 1882. Possibly   Suffolk probate file no. 16844, d. cir 1905.

   12. Frances Penny; born 18 May 1814; married Oliver K. Buckley 6 Jan 1835;43 died 11 Jan 1892 at age 77.
    Children of Frances Penny and Oliver K. Buckley were as follows:

         i. Oliver K.; married Martha Webb; married Emma Welch.
         ii. Capt. George B.; married Harriet Sophia Young, daughter of Madison W. Young and
         Miranda Penny, 14 Feb 1859;11 died 21 Aug 1892.
 He was captain of the bark " William Hall."He and Harriet Sophia Young were murdered in their berths by a lascar (East Indian sailor) on a voyage to Cape Town. Both  were buried at sea.
         iii. Alonzo C.; married Mary Preston Griffin.
         iv. Sarah E.; married John Terry.
         v. William J.; married Susan Wells; married Minnie Skidmore.
         vi. Infant.
         vii. Gertrude J.; married Jesse Horton.
         viii. Ruth C..
         ix. Kate F.; married William Stockweather.

Click here to read The Life and Adventures of Joshua Penny a native of Southold who was impressed into the British Service, his escapes and true adventures.