All records cited here have been copied or abstracted  by me from Original Documents at the Maryland State Archives in Annapolis, MD, unless otherwise stated.    In my writing I use the generic form -- Pennington.  In the abstracts  have used  standard abbreviations,  plus  CC for Cecil County, Sip signed in presence [of]; SS  St. Stephens record. 
          The first Henry Pennington took up  his first  recorded Cecil County Patent  in 1671 when he purchased  Happy Harbour from Richard Leake    This is recorded in the Baltimore County records.  (Cecil was formed from both Baltimore and Kent Counties in        16 74.)  Other records suggest that he came to Cecil County after first living in St. Mary's County.      Little more is heard from him and the properties until they are devised in    1699 by the will of John Pennington, who left them to his brothers Henry, Robert,    Thomas and his "cozzen," (nephew during this time frame)  son of brother Henry. 
          Further on down the Chesapeake another mystery, Thomas I of Surry  County, VA raises  questions in my mind about whether he might have a connection to Cecil County          Penningtons.  I have often thought that this Thomas Pennington who died with a will  in 1702, (Peddington, Piddington) may have been attached to the Cecil family, possibly as a brother of Henry I.    There was also a William Pennington in Anne Arudel County who left two orphans, William and Thomas.  William may be another sibling of Henry I.
          There is nothing in the records to suggest that Henry I was the parent of Abraham, The Indian Trader, who lived along the Susquehenna and his brother John of Northeast.  John of Northeast  was a shoemaker and left 5 pounds to his brother, "Abram" in his will in 1736.

    John Pennington to brother Henry, all right, etc. to tract called Happy Harbour, cont. 400 acres of land.  To brother Robert fifty acres of land, a parcel formerly laid out for Jarvis Morgan.  To brother Thomas, parcel called Silvains Follly and all imp.  To brother Robert, a parcel called Buntington and all imp.  To Thomas 50 acress, part of Silvains Folly and Buntington, to Cozen John Penington, son of Henry Pennington, Pennyworth. 
          Temporal estate to Robert and Henry to be equally divided.  Witness:  John Hall, John Keys, Edward Laramore (h.m.)  (His Mark) William Garrish (h.m.) Proved 28 Feb 1699 
        There is great significance to this will.  First, since there is no will devising the properties from Henry to John,  an assumption can be made that Henry A died intestate and John was his oldest son and there fore  the properties simply passed to him.    It is interesting that John ostensibly is childless and wifeless.  I think he is childless and wifeless because he was a Roman Catholic Priest, also mentioned in the St. Mary's County records as purchasing property along with another R. C. Priest, Francis Pennington.  In one statement Francis deposes that he was born in 1734, and if he was  Henry A's son, the other brothers births can be  dated about the same time.

  Also in 1702, Thomas Pennington and his wife Alice/Allie/Ellie/Aelie sold their Cecil County holdings and disappear from the records there.  Thomas received Silvanias Folly from his brother John in 1699.  Thomas and Allie had three children baptized at St. Stephens Church:  Isaac, Thomas and Matthias. 
        The deeds:  p. 221 n. s. Sassafras River on Hacks Creek from S.E. of Peningtons land to land belonging to George Hack, cont. 100 ac.  Also 50 ac. of Buntinton devised by last will and test. of brother John.  Sip of Henry Ward; John Keys.  s/Robert Penington.  Ack. 5 Jun bef. Matt. Vanderhoyden, John Stoops.  Rec 5 June 
        P. 248   Allie consented to  this deed, p. 248  on  28 Nov 1702  "I, Ailse Peninton, now  wf to Thomas Penington planter consent to    deed of sale to John Atkey. Silvanes Follow, 50 ac. "  She empowers Robert Penington to make over property to John Atkey.  Mathias Vanderheyden;  John Hynsone. Ealie (h.m.) Penington (circle with spokes)  12 Jan 1702 Ack. by Robert Penington.  Rec. 21 Feb 1702    Allie's mark was used by the Wheelers, and was also used by Anne Pennington, wife of Robert. )

        On  p. 409 Thomas Pennington and Allie his wife to John Atkey   100 acres north side of the Sassafras  part of Buntington  50 acres part Silvanes Folley bequeathed by brother John .  Iin presence of Henry Ward and John Keys 10 Dec 1702  by Robert Pennington  before Matt Vanderhoydon John Stoops Jno Dowdall. It would seem they were gone by this time because Robert went ahead and transferred the property.

Mentions his loving wife.  Son Robert Peninton bequeathed 50 acres  that was  left by brother John Peninton  in his will. Beginning and  bounded by a banded chesnut tree standing in the woods being  a bounded on the north-east side of a parcel of land belonging  to OLIVER MATHIASON, running south-west by his line three  hundred and twenty paces to the Sasafras River, then by the  river south east one hundred and fifty paces. Cross a creek  called Duck Creek is a bounded tree of a parcel of land  formerly belonging to GARVIS MORGAN, by his line to the  chesnut more or less out of the land called Happy Harbour, for  his use forever. To son Henry Penninton  he bequeaths  plantation.      To brother-in-law Robert  Porter, when he comes of  age one mare, three years old.  Beloved friends: Jn(o) Coppin,  Thomas Cox(?). Witnesses: John Stoop, Jn(o) Coppin, Jn(o)  Cruikshank, Catherine Curth(onor? ) Cruickshank?) Mary Stoop.

Anne Pennington, James Morgan; John Crockshanke Presence of us:  Will Freman, John Copping
There is an additional account administration for Robert  Pennington, 1709/10, Box 2,              Folder 20    OR 26  which I have not examined.

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