Early Colonial Settlers of Southern Maryland and Virginia's Northern Neck Counties

Leonard Dr. Hollyday

Male Abt 1730 - 1793  (~ 63 years)


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  • Name Leonard Dr. Hollyday  [1
    Born Abt 1730  Prince George's County, Maryland Find all individuals with events at this location 
    Gender Male 
    Died 3 Dec 1793  Calvert County, Maryland - Probate Find all individuals with events at this location 
    Buried will recorded in Prince George's County, Maryland Find all individuals with events at this location 
    Person ID I015041  Tree1
    Last Modified 3 May 2021 

    Father Leonard Hollyday,   b. 4 May 1691, Calvert County, Maryland now Prince George's County, Maryland Find all individuals with events at this location,   d. 26 Jun 1741, Prince George's County, Maryland - Probate Find all individuals with events at this location  (Age 50 years) 
    Mother Sarah Smith,   b. Aft 1690, Calvert County, Maryland now Prince George's County, Maryland Find all individuals with events at this location,   d. 1731, Prince George's County, Maryland Find all individuals with events at this location  (Age < 39 years) 
    Married Abt 1711  Prince George's County, Maryland Find all individuals with events at this location 
    Family ID F08130  Group Sheet  |  Family Chart

    Family 1 Grace Contee,   b. 1738, Prince George's County, Maryland Find all individuals with events at this location,   d. Abt 1755, Prince George's County, Maryland Find all individuals with events at this location  (Age 17 years) 
    Married Abt 1751  Prince George's County, Maryland Find all individuals with events at this location 
    Children 
     1. Leonard Hollyday,   b. 1754, Prince George's County, Maryland Find all individuals with events at this location,   d. Between 1779 and 1795, Prince George's County, Maryland Find all individuals with events at this location  (Age 25 years)
    Last Modified 3 May 2021 
    Family ID F09728  Group Sheet  |  Family Chart

    Family 2 Sarah Bradley,   b. Abt 1735, Prince George's County, Maryland Find all individuals with events at this location,   d. Bef Nov 1777, Prince George's County, Maryland Find all individuals with events at this location  (Age ~ 42 years) 
    Married Abt 1755  Prince George's County, Maryland Find all individuals with events at this location 
    Children 
     1. Sarah Hollyday,   b. Abt 1755, Prince George's County, Maryland Find all individuals with events at this location,   d. Bef 13 Aug 1782, Prince George's County, Maryland Find all individuals with events at this location  (Age ~ 27 years)
     2. Anne Bradley Hollyday,   b. Bef 1762, Prince George's County, Maryland Find all individuals with events at this location,   d. 8 Jun 1802, Prince George's County, Maryland - Probate Find all individuals with events at this location  (Age > 40 years)
    Last Modified 3 May 2021 
    Family ID F09729  Group Sheet  |  Family Chart

  • Notes 
    • ===
      Prince George's County MD Will Book Liber T No. #1
      1790-1796;
      Folio 339 LEONARD HOLLYDAY, of Calvert County 08/12/1777 12/03/1793
      -being weak in Body
      Bequeaths to;
      1. Leonard Hollyday --son
      -to have all of testator's lands lying in Calvert County called -"Buzzard Island- and "Addition to Buzzard Island" and part of "Arnold's Purchase- and to have all of testator's lands lying in Prince George's County called Brookefield and '`Hollyday's Wild Goose Meadow"
      -to have all of testator's lands tying in St. Mary's and Charles Counties
      2. Sarah Johns --daughter
      Ann Bradley Hollyday --daughter
      -should testator's son Leonard die w/out issue, then to have the lands left to hint and should they die w/out issue then to descend as per the will of testator's father Leonard Hollyday
      -should Leonard die w/out issue, then to have lands lying in Charles and St. Marie's Counties,
      -testator's three children to have all die personal estate to be divided equally among.. them
      3. Thomas Johns --son-in-law
      -named executor along w/ testator's son Leonard
      Witnesses: Margaret Skinner, Benjamin Mackall 4th, Benjamin Mackall
      Then came: Benjamin Mackall 4th and Benjamin Mackall
      Note the testator signed the will in his own hand
      ===
      EFSM Vol 7 - Minor in 1744
      ===
      Across the Years In Prince George's County

      Hollyday, Leonard. gent., Prince George's County, 7th Nov., 1739; 26th June, 1741,
      To son Thomas and male hrs., 1100 A, dwelling plantation and tracts adjoining "Holydays Wild Goose Meadow" and "Crews Meadow" also "Burnt House" and "True Man's Acquiantance" and House and lot in Nottingham, Shd. he die without male hrs, afsd. tracts to pass to son Leonard and male hrs, and son Clement and male hrs, and in default of any such hrs. to dau. Elizabeth and Mary.
      to son Leonard and male hrs., "Buzzard Island" in Calvert Co. and "Newells. Adventure."
      to son Clement and hrs., 1600 A. "Indian Creew" St. Marys County, "Nottingham" Charles Go.
      to wife - and child. Thomas, Leonard, Clement, Elizabeth and Mary, personal estate.
      to nephew Leonard Covington, bro. James and sis. Marjory Gantt, personalty,
      Son Leonard to be kept at school with Rev, John Eversfield until he is capable of studing Divinity, Physic or Law and then be placed with some gentleman who is capable of teaching him the profession he choses.
      At no time shall any child. be under guardianship or education of a Roman Catholic.
      Exs.: Wife and son Thomas.
      Overseers: Bro. James Hollyday, bros.-In-law Thomas Gantt and John Smith, nephew Leonard Covington and friend Alexander Contee.
      Test: Dr. James Boswell, Anne Waring, Sarah Greenfield,
      Thomas Gantt. 22.359.
      ===
      BRADLEY, ROBERT, Prince George's Co. 7 June 1769; 1 Dec 1772
      To dau, Millicent Beall, 50 and as her grandfather Clement Hill left: her part of tract of land 500 acres that is why I did not give her as much as her two sisters.
      To 2 granddaus. Sarah and Anne Bradley Hollydays daus, of my dau. Sarah and Dr. Leonard Holyday of Calvert Co,,, tract "Addition to Mooresfield" In Prince George's County adjoining "Four Hills" and "Berry's Fortune."
      To 2 daus, Elianor Tyler and Mary Bradley, extx., all of personal estate and tracts "Four Hills," part of "Bacon Hill."
      part of Samuel Bealls "Beginning Moor Craft" and "Moores LittleWorth," 450 acres, so that each get 225 acres.
      Son-In-law, Robert Tyler, ex.
      Wit: Jane Threlkeld; Thom's. Clagett; Joseph Threlkeld. 39. 22
      ===
      Dr. Patrick Sim 20.189 A PG 1692.6.7 1434.1.0 May 10 1744
      Received from: John Skinner, Robert Bradley, Leonard Hollyday, James Hall, Thomas Gaunt, Sr., William Digges, Jane Contee, John Martin, Edward Claggett, Anne Brooke, John Bowie, Jr., widow of Clement Brooke, William Smith, Charles Digges, James Bowie, John Smith, Thomas Crompton, Leonard Covington, John Lawson, Henry Hill, Francis Crandall, Osburn Sprigg, Clement Hill, Sr., John Hepburn, Mr. William Black, Mr. William Torver, Richard Moleanux, John Darnal, Thomas Hodgkin, John Bowie, Sr., Capt. Shakespear, Thomas Brooke, Madam Sprigg, Thomas Denwood, widow Offutt, William Mordock, William Brogden, Thomas Cleland, Ceesar Grice, widow Tasker, William Young, Richard White, John Bourne, Jr., Nathaniel Selby, Basil Waring, Leonard Hollyday, Hooper Green, John Blanford, Henry Watson, Mary Townley, Anne Russell, Gabriel Swain, the County, Charles Hodge, Capt. Belt, Randolph Johnson, Mackell Skinner, Solomon Docura, Thomas Warring, Richard Keene, Richard Beans, James Kelly, David Craford, John Levitt, Capt. James, Leonard Decan, Mr, Dick, William Tinch, Jr., John Becket, Charles Beall, Robert Perrie, Edward Sprigg, James Pummer, William Beall, widow Williams, Mark Webb, John Boone, Sr., Mr. Hardin, Mr. Jameston, Alexander Beall, Henry Wharton, Maurice Morris, Richard Beanes, John Sprigg, John Bowrey, Lingan Wilson, John Perrie, Leonard Dea, John Orm, Thomas Sprigg, Madam Sprigg, William Reed, John Griffwell, Thomas Ragan, John Brightwell, Pau Rawlings, Henry Lee, Thomas Charter, widow Maconchie, James Harvie, Thomas Comes, Samuel Harvey, Mrs. Boswell, Mr. Robert Mitchell, Benjamin Walorsporo, William Mills Magruder, Mrs. Duval, Thomas Blanford, Samuel Harris, Mark Webb, Nat. Smith, widow Parker, William Hardie, Samuel Warring, Philip Lee, Esq., Robert Mills, Thomas Selby, John Johnston, John Peirce, widow Clagget, Witham Buston, Henry Buttler, James Thomas, Daniel Carroll, Samuell Busey, Thomas Austin, James Yong, Mr. Bolton, Mark Marshall, Allan Bowie, Philip Briscoe, Richard Jarvin, Peter Smith, Benjamin Walmsford, Arnold Livers, Francis King, Addison Sheaperd, Al. Bussel, Aaron Roberts, Marry Ragget, John Lange, Benjamin Craycroft, Madam Addison, Edward Digges, Peter Courcill, Francis Herbert, Jame Swann, George Gordon, John Smith Prather, Ingnatius & Nicholas Digges, William Jones, Thomas Hamilton, John Craycroft, Clem Craycroft, John Hawkins, William Nicholus, William Groome, John Hepburne, Samuel Warring, John Johnson, Jame Dair, Samuel Taylor.
      Payments to: Clement Smith who married a daughter (unnamed, her portion), Thomas Lee who married a daughter (unnamed, her portion).
      Administratrix: Mary Sim.
      ===
      KING, THOMAS, 18 Nov, 1754; 20 Mar, 1755
      To sister Margaret Hillary, 5 s. sterl.
      To sister Cave Williams, 5 s.
      To son-in-law John Brooks, my wife Martha King, 2/3 personal estates
      RemainIng pt. of personal estate to bro. Francis King; all real estate to said bro. Francis King.
      Wife Martha King, and bro. Francis King, exs.
      Wit: L. Hollyday,. Clement Hollyday, Benj. Mackall.. Jr. 29.. 417
      ===
      PRINCE GEORGE'S COUNTY, MARYLAND WILLS; Liber T No. #1; 1784-1789;
      Folio 194 HENRY BROOKE, mariner 03/30/1772 06/14/1784
      "being at this present time of sound mind memory and understanding
      Bequeaths to:
      1 Mary. Brooke --wife
      -to have one third part of the personal estate
      -to have for her natural life or widowhood the one third part of testator's real estate
      -named executrix and to have the entire estate both real and personal until testator's son Henry comes of age.
      2 Henry Brooke --son
      -at widow's decease to have the thirds of the real estate left to her.
      -to have the rest and residue of the estate both real and personal wi exception
      3. Margaret Brooke --mother
      -to have the part of the meadow ground now in her possession during the term of her natural life and instructs her that the land give!' to testator's son Henry and that where she Jives is to be cut down for logs and wood during her natural life for her support on the condition that should Henry come of age 21, then to have his share of the land
      -should testator's son Henry die before coming of age, then to have Negro boy "Tom' and "Ben" provided she make no claim against the estate for the sum of 40 pounds sterling which testator owes her
      4. Nicholas Brooke --brother
      -should widow die or remarry before testator's son comes of age, then to have all of testator's estate both real and personal
      5. Elizabeth Brooke --daughter
      -to have 5 shillings sterling
      Witnesses: John Harrison
      L. Hollyday
      Catherine Harrison
      Then came: John Harrison and Leonard Hollyday
      Note: the testator signed the will in his own hand
      ===
      PRINCE GEORGE'S COUNTY, MARYLAND WILLS; Liber T No. #1; 1784-1789;
      Folio 283 ANN SKINNER 12/2 1/1782 09/25/ 1789
      "being of sound mind and memory ..."
      Bequeaths to:
      I. Alexander Skinner --son
      -to have Negro women "Lucy" "Nan" "Myrtee" and "Sylvia"
      -to have all of testatrix's lands.
      -to have the residue of the goods and chattels
      2. Benjamin Contee
      -named executor of the will
      Witnesses: Leonard Hollyday, Leonard Hollyday, Jr. Walter B. Cox
      Then came: Leonard Hollyday, Sr.
      ===
      ===
      Provincial Court Land Records, 1765-1770
      Volume 725, Page 218

      This Indenture made this twenty second day of May in the Year seventeen
      hundred and sixty seven Between John Rogers of the one part and Leonard Hollyday
      of the other part Whereas for the docking barring and extinguishing all Estates
      Tail and Reversions or Remainders thereupon expectant or depending of and in
      the Lands and Appurtenances herein after mentioned the said John Rogers as
      Demandant did heretofore (at the request cost and charges of the aforesaid Leonard
      Hollyday) prosecute and sue forth out of his Lordships high Court of Chancery his
      said Lordships Writ of Entry sur Disseisin en le post against him the said Leonard
      Hollyday returnable and returnable to the Provincial Court at Annapolis the third
      Tuesday of May whereby the said John Rogers did demand against him the said
      Leonard Hollyday All those following several tracts or parcells of plantable Land
      lying and being in Prince Georges County viz.t All that tract or parcel of plantable
      land called Brookefield originally granted to a certain Thomas Brooke and
      Baker Brooke for two thousand five hundred and thirty acres All that tract or
      parcell of plantable Land called Hollydays Wild Goose Meadow containing two
      hundred and twenty seven acres and all that tract or parcell of plantable Land
      called Chews Meadow containing One hundred acres being the Same several tracts
      or parcells of land heretofore devised by Leonard Hollyday deceased to his son
      Thomas Hollyday deceased in tail Male remainder to his son the first aforesaid
      Leonard Hollyday in Tail male To which said writ the said Leonard Hollyday
      the son party hereto did appear in his proper person and vouch to warrant thereof the
      common vouchee of the same court and such further and other proceedings were
      thereupon had that the said John Rogers did by Judgment of the same court recover
      his Seisin against the said Leonard Hollyday party hereto of and in the Demanded
      premisses and the said Leonard Hollyday party hereto did recover over in value
      against the common vouchee whereby a common Recovery of the aforesaid premisses hath
      been had and Suffered Now this Indenture Witnesseth that for the
      setling and declaring the intent and use of the said Recovery and for and in
      consideration of five Shillings Current Money by him the said Leonard Hollyday party
      hereto to the aforesaid John Rogers in hand paid the receipt whereof is hereby
      acknowledged it is hereby covenanted granted agreed and declared by and between the said parties
      to these presents at the said Common Recovery so as aforesaid or in any other manner had and
      Suffered and the Execution thereof from and immediately after the Suffering the Same or any other
      Recovery or Recoveries of the said mentioned premisses or any part thereof was meant and
      intended to be and enure and it is hereby declared to be and enure and that the Recoveror therein
      named and his heirs should and shall Stand and be Seised of and in the Recovered premisses
      and every part and parcell thereof to and for the only proper Use and Behoofe of the said
      Leonard Hollyday party hereto his heirs and assigns forever and to or for no other use
      Intent or purpose whatsoever In Witness whereof the parties to these presents have
      hereunto interchangeably set their hands and affixed their Seals the day and year first above
      Written J Rogers (Seal)
      Signed Sealed and Delivered
      in the presence of us
      Baruch Williams L Hollyday (Seal)
      Rich.d Butler

      On the Back of the Aforegoing Deed was thus Written viz.t

      Received on the day and year first within Written of and from the within named Leonard
      Hollyday party hereto the sum of five Shillings Current Money being the Consideration Money
      within mentioned to be by him paid to me
      Witness Received by me
      Rich.d Butler J Rogers
      Baruch Williams

      On the twenty second day of May 1767 Came before me the Subscriber one of his Lordships
      Justices of the Provincial Court the within named John Rogers and Leonard Hollyday and
      Severally acknowledged the within Deed to be their respective Act and Deed to and for the
      uses intents and purposes within Mentioned and the Land and Premisses therein mentioned
      to be the Right and Estate of the within named Leonard Hollyday party thereto his
      heirs and Assigns for ever according to the true intent and meaning of the same Deed and
      the Act of Assembly in such case made and provided
      6 sides
      Recorded the 22.d May 1767 Dan of S.t Tho.s Jenifer
      ===
      Prince George's County, Maryland Land Records 1767-1769; Liber BB 2 {Abstract by Mike Marshall}; Page 163. At the request of Leonard Hollyday the following Land Commission was recorded December 8, 1767
      Memorandum that on the special petition of Leonard Hollyday preferred to the justices of Prince George's County, Maryland on the 4th Tuesday in June in the 13th year of his Lordship commission the Right Hon. the Lord Proprietary Dominion etc., his Lordship commission issued by order of the justices aforesaid out of the county aforesaid on April 10, 1764 in these words following, Frederick Absolute Lord and Proprietary of the Province of Maryland and Avalon Lord Baron of Baltimore vizt; to Messrs George Gordon, Joseph Sim, William Lock Weems and Benjamin Brookes of PGCo Gentleman, whereas Leonard Holliday, is seized of several tract tracks called "Moore's Fields", "Battenwick", "Four Hills" and "Berry's Fortune" and preferred his petition in writing to our county court held at Upper Marlbro Town to examine evidence to prove and perpetuate the memory of the bounds of the said tracts of land. Therefore, we command you any three or two of you to examine all witnesses or persons concerned touching their knowledge of the bounds of the said tract. Witness Francis Waring, Gentleman, March 31, 1764 issued April 10, 1764, Joseph Sim, Clk
      By virtue of a commission to examine evidences to prove the bounds of several tract tracks called "Moore's Fields", "Battenwick", "Four Hills" and "Berry's Fortune" we intend to meet on July 21 next, June 1, 1764, Joseph Sim, Benjamin Brookes
      John Clagett aged about 80 years being at a bounded black or red oak standing at the side of a hill of an old field declares he has often heard and always understood the said tree to be the beginning tree of "Greenland" and then he further understood that the lands which was held by Benjamin Berry and now in possession of Dr. Leonard Hollyday came to this tree and further saith not
      John Clagett aged 80 being at a small dogwood tree standing on a gravelly nnoll where formerly stood a bounded oak declared he has often told it was the second bound tree of "Greenland" and further saith not
      Robert Bradly aged 64 years being at an old black oak now lying down and decayed near the mouth of Deep Branch and about 20 yards from St. Charles Branch declares he was told about 20 years ago but can't recollect by whom that it was a bound tree of Berry's land now in possession of Dr. Leonard Holliday and further saith not
      ===
      Prince George's County, Maryland Land Records 1767-1769; Liber BB 2 {Abstract by Mike Marshall}; Page 163. At the request of Leonard Hollyday the following Land Commission was recorded December 8, 1767
      Memorandum that on the special petition of Leonard Hollyday preferred to the justices of Prince George's County, Maryland on the 4th Tuesday in June in the 13th year of his Lordship commission the Right Hon. the Lord Proprietary Dominion etc., his Lordship commission issued by order of the justices aforesaid out of the county aforesaid on April 10, 1764 in these words following, Frederick Absolute Lord and Proprietary of the Province of Maryland and Avalon Lord Baron of Baltimore vizt; to Messrs George Gordon, Joseph Sim, William Lock Weems and Benjamin Brookes of PGCo Gentleman, whereas Leonard Holliday, is seized of several tract tracks called "Moore's Fields", "Battenwick", "Four Hills" and "Berry's Fortune" and preferred his petition in writing to our county court held at Upper Marlbro Town to examine evidence to prove and perpetuate the memory of the bounds of the said tracts of land. Therefore, we command you any three or two of you to examine all witnesses or persons concerned touching their knowledge of the bounds of the said tract. Witness Francis Waring, Gentleman, March 31, 1764 issued April 10, 1764, Joseph Sim, Clk
      By virtue of a commission to examine evidences to prove the bounds of several tract tracks called "Moore's Fields", "Battenwick", "Four Hills" and "Berry's Fortune" we intend to meet on July 21 next, June 1, 1764, Joseph Sim, Benjamin Brookes
      John Clagett aged about 80 years being at a bounded black or red oak standing at the side of a hill of an old field declares he has often heard and always understood the said tree to be the beginning tree of "Greenland" and then he further understood that the lands which was held by Benjamin Berry and now in possession of Dr. Leonard Hollyday came to this tree and further saith not
      John Clagett aged 80 being at a small dogwood tree standing on a gravelly nnoll where formerly stood a bounded oak declared he has often told it was the second bound tree of "Greenland" and further saith not
      Robert Bradly aged 64 years being at an old black oak now lying down and decayed near the mouth of Deep Branch and about 20 yards from St. Charles Branch declares he was told about 20 years ago but can't recollect by whom that it was a bound tree of Berry's land now in possession of Dr. Leonard Holliday and further saith not
      ===
      1773-1778 Frederick County Land Records; {Patricia Abelard Andersen}
      W:442-444. Thomas Contee and Doct. Leonard Hollyday of Prince George's County, recorded deed 23 Dec. 1775, from Thomas Warring for 150 sterling, tract Warington, on bank of Potomac River, across from Swan Pond Bottom in Virginia, containing 270 acres more or less.

  • Sources 
    1. [S044774] Early Families of Southern Maryland, Volume: 7.

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