Honorable Capt. John Dorsey of "Hockley-in-the-Hole" ^{1 2 3 4 5 6 7 8}

   Other names for John were Honorable John Dorsey of "Hockley-in-the-Hole" and Captain John Dorsey of "Hockley-in-the-Hole."

  Research Notes:

Youngest son of Edward, the colonist. Patented "Hockley-in-the-Hole" on the south side of the Severn with his brothers Edward and Joshua in 1664. Acquired "Troy" around 1699.
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From Side-Lights on Maryland History, Vol. 2, pp. 87-91:

"Hockley-in-the-Hole, originally taken up by Edward Darcy, was in 1664 patented to his sons Edward, Joshua and John, the original patent bearing date August 20, 1664, being still in the possession of the present owner of Hockley, Miss Anne Elizabeth Dorsey, lineal descendant of all three of the original patentees. In the year 1681 'Edward Dorsey, Gent. of Ann Arundell County, Son and heir of Edward Dorsey late of said County deceased' assigned his right to his brother John. The parchment document granting Hockley to the three Dorsey brothers bears the autograph of Charles, third Lord Baltimore, and was given under the Great Seal of the Province.

"[Major Edward Dorsey's] house on Prince George's Street, Annapolis, was probably built when he disposed of his interest in Hockley to his youngest brother the 'Honorable John Dorsey.'

"... the Honorable John Dorsey, captain of the Baltimore County militia in later years, took possession of Hockley, three miles from Annapolis, over which his wife, Madam Pleasance Ely, presided, of whom it has been noted--perhaps as a warning to her descendants, that her name was in no sense suggestive of her disposition."
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From The Founders of Anne Arundel and Howard Counties, Maryland, p. 56:

"The following record is taken from 'Our Early Settlers.'--A list of our early arrivels [sic] up to 1680.

"'Robert Bullen demands lands for bringing over a number of passengers, amongst whom was Edward Dorsey, in 1661.'

"The same record adds, 'Aug. 25th [20th], 1664, patented to him, John and Joshua Dorsey, a plantation called "Hockley-in-the-Hole," four hundred acres.'

"In 1683, this land was resurveyed for John Dorsey, and found to contain 843 acres. 400 acres first surveyed being old rents remaining new, whole now in the possession of Caleb Dorsey.

"Such is the record of 'Hockley' upon our Rent Rolls, at Annapolis."

Ibid., p. 30:
"In 1664, the three sons of Edward Dorsey, the immigrant of 1650--relatives of the Howards--took up and patented their father's survey of 'Hockley-in-the-Hole.' They were Colonel Edward Dorsey, Joshua and Hon. John Dorsey, prominent leaders in political movements and representatives in legislative measures."

Ibid., pp. 61-62:

"HON. JOHN DORSEY, OF 'HOCKLEY.'

"Coming into possession of 'Hockley,' in 1683, Hon. John Dorsey married Plesance Ely, who later took up a tract of land on Elk Ridge, which she named 'The Isle of Ely.' In 1694, Hon. John Dorsey, was a commissioner for the development of Annapolis. He was upon many important committees during his service in the Lower House of the Assembly. In 1711, he was advanced to the Upper House, and there remained until his death in 1714. During his life-time he was a surveyor of a vast estate of valuable lands. He left an exceedingly intelligent will of entail, which gives a summary of his large estate. It reads: 'My wife, Plesance, is to have one-third of my estate, and also the choice of my estate on South River, or my now dwelling place on Elk Ridge [Troy]. To my grandson, John Dorsey, son of my son, Edward Dorsey, deceased, my Patuxent plantation and lands thereunto adjoining called 'Dorsey's Search,' lying in Baltimore County. If no issue, to go to the three youngest grandchildren of my daughter, Deborah

'I give to my grandson, Edward Dorsey, son of my son, Edward Dorsey, de ceased, "Dorsey's Adventure" and "Whitaker's Purchase" adjoining it. If he leave no issue, then to John, of Edward, and if he leave none, then as above, to Deborah's youngest three children. To my grandsons, Charles and William Ridgely, of Deborah, my tract called "White Wine and Claret," south side of the middle branch of the Patuxent. If they leave no issue, to go to Martha, Elinor and Edward Clagett.

'I give to my two grandsons, Samuel and Richard, of Caleb, my son, my plantation on South River, called "South River Quarter," it being the remainder of a tract given to my son, Caleb. In case of no issue, the same to go to granddaughters, Achsah and Sophia of Caleb.

'To grandson, Basil, of Caleb, my plantation on Elk Ridge, called "Troy." If no issue, to my grandsons, John and Caleb, of Caleb. My son, Caleb, to be my administrator.--JOHN DORSEY. (Seal.'

"Mrs. Plesance Dorsey became Mrs Robert Wainwright. Her tract, 'The Isle of Ely,' was sold by her grandson, 'Patuxent John Dorsey,' to Basil Dorsey, of Caleb, whose homestead, 'Troy Hill,' was the former residence of Hon. John Dorsey."

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From http://genforum.genealogy.com/norwood/messages/1247.html:

Notes for Captain John Dorsey:
[Ancestors of Abednego Baker by Muriel Schulz.ged]

From Anne Arundel Gentry, p. 10:
Edward Dorsey II before 1683 assigned to his brother, John, his portion of 400 acres for 24,000 lbs. Tobacco. Joshua, the second son, had conveyed his portion of "Hockley" for 8,000 lbs. Tobacco. In 1685 Caleb Dorsey, son of John, had the plantation resurveyed and found that it contained 843 acres instead of the original 400.

[Page 10]: 1681 - Deed from Edward Dorsey II, to John Dorsey:
Edward Dorsey of the County of Anne Arundel Gent son and heir of Edward Dorsey late of the County of Anne Arundel . . . deceased. . . whereas the Rt. Honorable Cecillius Lord Baron of Baltimore by his pattent bearing date the twentieth day of August one thousand six hundred and sixty four for ye Consideration therein mentioned Grant unto the said Edward Dorsey, Joshua Dorsey and John Dorsey my brothers a parcell of land Called Hockley in ye Hole lying in Anne Arundel County aforesaid on ye South side Seaverne River in ye Woods beginning at a marke Oake being a bound tree of the land of Cornelius and Samuell Howard . . . . the said four hundred Acres of land unto the said Edward Dorsey, John Dorsey and Joshua Dorsey . . . . Now know ye that I the said Edward Dorsey for & in consideration of Twenty four Thousand pounds of good sound merchantable leafe tobacco to me in hand paid by my said Brother John Dorsey the receipt whereof I do hereby acknowledge and thereof of every part & parcell thereof do acquitt and discharge the said John Dorsey . . . . . and quit claim unto my said brother John Dorsey now in possession of the said four hundred Acres of land . . . . by virtue of ye aforesaid pattent or grant of ye sa Lord Baltemore to me the said Edward Josua and John Dorsey in Joynt tenancy as aforesaid or by virtue of any with Same or demand that may or might demand or accrue from my said father Edward Dorsey deceased . . . . Sixth day of December in ye Yeare of our Lord One thousand Six hundred Eighty one."

The indenture was witnessed by Richard Hill and Nicholas Greenbury. Ref. A.A. Co. Deeds, Liber IH:, No. 3, folio 62-63, Hall of Records, Annapolis.


The inventory of his personal estate was taken on April 25, 1715 and filed by his son and executor, Caleb Dorsey. At the home-plantation there were 11 slaves and in "ye new Roome" were books and a pair of spectacles. His quarters at Elk Ridge had five slaves, the Patuxent Quarters four slaves, but none was listed at the South River Quarters. The entire estate was appraised at 1440/3/9 with credit due from merchants in London. Richard Clagett and John Dorsey approved as the next of kin.

He apparently had a state funeral and certainly one in which the mourners and friends enjoyed traditional Maryland hospitality. At an account filed on April 11, 1716, 10 gallons of rum and 30 gallons of cider were consumed as well as cakes costing 2 lbs. The Rev. Williams Tebbs who preached the funeral sermon was given 2 lbs. At that time the widow was allotted her third, that is 321/8/3 plus 4/154 lbs. tobacco.

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From http://www.eskimo.com/~bgudgel/gudgarc1 :

Sometime around 1658 Edward Dorsey took up a tract of land containing 400 acres, lying in Anne Arundel County on the south side of the Severn River and or a branch of Broad Creek. This tract was later patented by his three sons. See Patents 7, f.378. In the year 1664 there was granted to Edward, Joshua and John Dorsey, 2,000 acres of land lying on the Severn River, not far from where the city of Annapolis now stands. A part of this, called "Hockley-in-ye-Hole" (hole meaning valley) which remained interminably in the hands of the descendants of John Dorsey to the present time. In 1681, Major Edward Dorsey transferred his interest in Hockley-in-the-Hole to his brother John. The transfer reads: "To all Christian People To Whom This Writing Shall Come, be Heard or Seen: I, Edward Dorsey, of the county of Anne Arundel, son and heir of the late Edward Dorsey, gentleman, deceased, for the consideration of 24,000 pounds of good merchantable tobacco, transfer my right in a tract of land called "Hockley-in-the- Hole" granted to Edward, Joshua and John Dorsey in 1664 to my brother, John Dorsey; and I further covenant to guarantee his right to said land against any demand that may descend from my said Father, Edward Dorsey, for or by reason of any right due to him in his lifetime or by reason of any survey by him made, or warrant returned, or for any other reason or any other matter." "Hockley" in the valley had pleasant environments. To the east, toward Annapolis, was the Carroll estates; to the north was the home of Gen. John Hammond; to the northwest were the lands of Cornelius, Samuel and John Howard; to the southwest was "Todd's Gap" through which the road to Lancelot Todd's led, and to the south the ancient Dorsey "God's Acre" which has since been abandoned for the family burial spot within the charming gardens of "Hockley" itself.

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From http://wc.rootsweb.ancestry.com/cgi-bin/igm.cgi?op=GET&db=mrmarsha&id=I36906:

Dorsey, John, Honorable,Balto. Co.,26th Nov., 1714; 22nd Mch., 1714-15.
To wife Pleasance, 1/3 of estate, real and personal, she to make choice of plantation -- , on South R., or dwelling plantation -- , on Elk Ridge.
To grandson John, son of son Edward, deceased, and his hrs., the Patuxent plantation "Dorsey's Search," in Balto. Co.; he dying without issue, to pass to grandson Edward, son of son Edward, and he dying without issue, to 3 young. child., -- , of dau. Deborah Clegat.
To grandson Edward afsd., and hrs., plantation "Dorsey's Adventure" on Elk Ridge, Balto. County, also "Whiteaker's Purchase," bought of James Barley; He dying without issue, sd. land to pass to grandson John afsd. and hrs., and then to child. of dau. Deborah as afsd.
To grandsons Charles and Wm. Ridgley, sons of dau. Deborah, equally, and their hrs., "White Wine and Claret," on s. side Patuxent R., in Balto Co.; they dying without issue, sd. tract to pass to Martha, Elinor and Edward Clegatt, child. of dau. Deborah, and hrs.
To grandsons Sam'll and Rich'd Dorsey, sons of son Caleb, and hrs., plantation "South River Quarter," being residue of a tract given by deed of gift to son Caleb. Sd. land to be in possession of wife during life as afsd. should she so select; and should grandsons afsd. die without issue, to pass to granddaus. Acksah and Sophia and their hrs.
To grandson Bazill and hrs., son of son Caleb, plantation "Troy," in Balto. Co.; he dying without issue, to pass to grandsons Jno. and Caleb Dorsey, sons of son Caleb afsd.
To grandson John, son of Edward, deceased, personalty, to be held by his mother, -- , until he is 21 yrs. of age; and to grandchild. Charles, Ridgely, 2nd son of dau. Deborah, and other grandchild. afsd., personalty. Boys to receive their estate at 21 yrs.
To dau. Deborah Clegatt, personalty.
Son Caleb, ex. and residuary legatee of estate.
Test: Joseph Howard, Thos. Higgens, Sam'll Dorsey, Thos. Rogers, Jno. Beale, Vachel Denton. 14. 26.

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From http://freepages.genealogy.rootsweb.ancestry.com/~paxson/southern/dorsey.html:

John Dorsey², was born ca. 1645 in Lower Norfolk County, Virginia, the son of Edward and his wife Ann, and died in 1715 in Maryland. He emigrated with his family in 1649 to Anne Arundel County, Maryland. John married in 1684 Pleasance ELY . One source identifies her as the step-daughter of Thomas WAINWRIGHT (d. 1729), while another states Thomas was her second husband. John is usually referred to in the records as "Hon." or Captain, a rank he held from 1695 until his death in 1714/5. Although raised as a Friend, he was later identified as Protestant, meaning neither Quaker or Anglican.[19]

"In 1663 John was living with his brothers at "Hockley in the Hole", Anne Arundel County, because it was surveyed for them on 27 January that year. This 400 acre plot had been taken up by their father sometime before 1658, on the south side of the Severn "and or a branch of Broad Creek". In 1681 John bought out his brothers' rights to it. He paid Edward 24,000 pounds of tobacco for it and additional land Edward had bought, and paid 8,000 pounds to Joshua. When it was resurveyed in 1683 (or 1685) it was found to contain 842 (or 843) acres (or resurveyed in 1685 and contained 1,842 acres).[20] The secondary accounts of the original records are a little hard to interpret in large part because they don't always differentiate among the multiplicity of bureaucratic steps necessary to secure title to a tract of land. The original patent was in the possession of a descendent, Anne Elizabeth Dorsey, who was still living in the old homestead in 1913. A photo of that date shows a relatively small house with two dormers on the roof, one chimney at the left end of the photo, and a narrow porch with a roof two storeys high suported on thin columns. The house was nearly obscured with shrubbery.[21] When we went to find it in April 2004, there was a white historical marker on the road, but the two houses that might conceivably have been a remnant of the old homestead both looked twentieth century, to me.

"John purchased significant amounts of land during his life. A list of them, by their names, includes:[22]

"Howard's Heirship" (150 acres) purchased from Cornelius and Elizabeth HOWARD on 4 August 1679; they were the brother and sister-in-law of our John Howard ;
"Hockley in the Hole", purchased Edward's and Joshua's rights in 1681; resurveyed in 1683 and found to contain 842 acres (see above);
"Orphan's Addition", near "Hockley in the Hole", on 10 March 1697, which he gave to his son Caleb on 6 August 1702;
"Dorsey's Adventure" (400 acres on Elk Ridge between the Patuxent and Patapsco) on 30 Feb [sic: perhaps April?] 1688; this tract with the next one were called "Patuxent Plantation", and were bequeathed to John's grandson, John Dorsey;
"Dorsey's Search" (479 acres) purchased on 6 December 1694 from James BAYLEY;
"Troy" (763 acres) on 12 October 1694;
"White Wine and Claret" (1,400 acres) on 6 January 1702;
"Whitaker's Purchase" (79 acres) in 1704;
"Roper's Increase" (100 acres) obtained on 14 February 1705 from Cornelius and Mary HOWARD;
"Mt. Gilboa" (245 acres) in 1706, which he conveyed the next year to Richard COLEGATE.

"On 12 June 1688 John and his brother Edward acquired land in what was then Baltimore County (now Howard County). Edward settled on his "Major's Choice", but John did not build on his "Dorsey's Adventure". Instead John commissioned surveyors to "go beyond Richard Warfield" in upper Anne Arundel County. There on 10 November 1695 he patented "Troy", 736 acres, between the present towns of Elkridge and Guilford, where he built his home. He also patented "Isle of Ely", named for his wife's family, and "Dorsey's Search". Another source says that Pleasance herself took up the tract after John's death, which she named "The Isle of Ely". The tax return of 1695 recorded, "John Dawsey's Quarter, on Elke Ridge, etc.", so John had a house there by that year. This makes "Troy" the oldest remaining house in Howard County, although it has been greatly altered. Originally "Troy" was a one-storey house with a front porch devoid of any ornamentation other than a simple ballustrade. Other floors were added later. The interior and exterior walls were about two feet thick. The old family burial ground was on one side of the house. The front porch now overlooks Meadowridge Cemetery (once part of the Dorsey estate) and route I-95. The entrance is from route 1 north of Dorsey Road.[23]

"John, like his brothers, probably opposed the Revolution of 1689. He gained his first appointed office from Governor Francis NICHOLSON who was sympathetic to the proprietor. From then on John had an active public career. He was appointed Justice of the Peace in Anne Arundel County in 1694 and 1696. In 1694 he was appointed to a commission charged with laying out the town and port of Anne Arundel in the County of the same name. On 17 May 1695 he petitioned the Assembly for a boat to carry the Burgesses of Anne Arundel County to St. Mary's. He was Captain in the Baltimore County militia in 1696. John served on a commission to oversee and direct construction of a Provincial prison in Annapolis. He was named to another commission to report on repairs to a house (purchased from his cousin Major Edward Dorsey) for the storage of public arms.[24]

"In 1692, after the consolidation of the reign of William and Mary in England, a new government was elected in Maryland that was very unsympathetic to Friends. They required an oath of allegiance in order to sit in the Assembly, and four Friends were immediately dismissed. The lower house tried to substitute an affirmation, but Governor Lionel COPLEY insisted on conforming to English practice. That year the Church of England was established, with a compulsary poll tax of forty pounds of tobacco. There were renewed efforts to force Friends to serve in the militia. The following year Friends were not permitted to give evidence in court unless they gave an oath. John Dorsey served as a member of the lower House of Assembly in 1692-93, and again in 1701-04 when a modified bill, rewritten by the Privy Council to meet some of the objections of Friends, was passed. It retained the 40 lb. tax to support the established church, and Friends continued up until the Revolution to suffer distraint of goods for refusing to pay it. In 1704 a bill was passed stipulating again that all office-holders must swear an oath.[25] I do not know how John felt about these attacks on his family's faith.

"John sat in the Lower House for Anne Arundel County in 1692-93 and 1701-04. He was appointed to the Provincial Council where he served from 1710/1 to 1714/5. On 18 January 1714 he described himself as "being lame and indisposed" and asked to be excused from the Council meeting. The following year the Council was said to consist of twelve "of the most able and discreet gentlemen" of the Province, including "John Dorsey, Esq., lately deceased."[26]

"John was a planter and merchant, somewhat more prosperous and less controversial than his older brother Edward. At the time of his first election, in 1692, John owned 1,242 acres. By 1696 he owned 2,484. In 1699 he was listed among the taxables on the South side of Patapsco, owning five slaves. Shortly thereafter he moved his family to "Troy", 763 acres at Elk Ridge, Baltimore County, which had been surveyed 12 October 1694. He took up 1,400 acres called "White Wine and Claret" between the present towns of Simpsonville and Clarksville in Howard County on 6 January 1702. The story goes that he sent out the surveyors with an ample supply of those liquid refreshments; when they returned with crooked lines, John figured that was the cause, and kept the name. The tax lists for Baltimore County sometimes indicate the number of slaves he owned at various plantations. In 1699 he had five on South Side Patapsco; in 1702 four, and in 1703 ten at Elk Ridge.[27]

"A few Friends were exercised about the institution of slavery, citing Jesus' injunction to do unto others as you would have them do unto you. But nothing was done at this time to rid the Society of Friends of this blemish. A few Friends were also exercised about the excessive use of tobacco. Hardshaw Monthly Meeting in Lancashire, Old England, minuted this advice 14 Fourth Month [June] 1691:

'It being considered that the too frequent use of smoking Tobacco is inconsistent with friends holy profession, it is desired that such as have occasion to make use thereof take it privately, neither too publicly in their own houses, nor by the highways, streets, or in alehouses or elsewhere, tending to the abetting the common excess.[27a]'

"Most Maryland Friends were oblivious of these movements that would impact so heavily on their economic and social well being.

"John signed his will in Baltimore County on 26 November 1714; it was witnessed by six men, one of whom signed with a mark. It was probated 22 March 1714/5. He left one third of his real and personal estate, after the payment of his debts, to his wife Pleasance as full payment of her dower. She was to be given her choice of either the plantation on South River or "my own dwelling plantation" on Elk Ridge. Her share of the estate included four human beings: Jacob and his wife Jenny, and two other Negro men, Lyman and Sambo. John's extensive real estate holdings and the remaining slaves were carefully apportioned to his grandchildren, with instructions for their further disposal if a given grandchild died with no heirs. His daughter Deborah was to be given £50, doled out at the rate of £8 per year "for her support", but no real estate. Her children were the third back-up to inherit if other grandchildren died without heirs. The residue went to his son Caleb, who was named executor. Nathaniell and Thomasin STINCHCOMB owed money to him.[28]

"An inventory of John's property was taken on 25 April 1715 by Thomas HAMMOND and John ISRAEL. The only values given in the Dorsey Family's copy were for the seventeen enslaved people. An odd assortment of items were listed "At the Home Plantation", "In the New Room", and "in the Kitchen". They included one silver tankard and one silver spoon; a dozen old leather chairs, six new leather chairs, and 4 "Turkey workt" chairs; an old sealskin trunk; a gun and 1/4 lb. of gunpowder; a small looking glass; one feather bed with canvas tick[ing], rug blanket, sheets, bedstead, and pillows; another feather bed and furniture, curtains and "vallens" [valence]; one pair Taylors Shears; a pair of money scales and weights; one parcel of new books; a pair of spectacles and case; 8 small brushes, 3 old combs, 3 pair sissors; 1 parcel of spice. There were lots of shoes, indicating the kind of merchandize with which John dealt: 2 dozen and 10 pair men's shoes, 3 pair women's shoes, 21 pair men's shoes. To go with them, 13 pair "large wove" stockings, 1 pair motheaten stockings, 20 pair of 4-thread hose, 5 pair women's thread stockings, 8 pair men's worsted hose, 1 pair large wove stockings. Then there was thread: 6.5 lbs. colored, 3 lbs. "Whited brown, coarse", 2 lbs. finer, 1 lb. brown, 1.5 lb. White and Brown, .5 lb. fine white, and about 1 lb. silk. John also had 6 gross Coat buttons and 6.5 gross Vest buttons, and about 5 gross fine thread [buttons?]. The only food mentioned was 1,692 lbs. of bacon. Negroes were listed "in the Kitchen": 2-year-old girl Beck; 6-year-old boy Sambo; 4-year-old boy Roger; 10-year-old girl Sarah, "much hurt by fire"; a "dropsical man" Jack; men named Jack and Tom, and one without a name; a woman, Beck, and young (unnamed) girl with child. The total value of these ten people was a mere £163 and 10d. At the Elk Ridge House there was ten lbs. of old pewter, a punch bowl, and more enslaved people: men named Simon, Sambo, Jack, and Toby; a woman named Jenny, a one-year old girl named Hagar and another girl (age not listed) named Juno. They were valued at £157. Other, unspecified items were at "Pattuxant Quarter", at South River, and at the "New Design". He probably owned about 5,000 acres; his estate was valued at £2,752.11.1.[29]

"Pleasance, "of austere memory" was described in family records: "between her name and her disposition there was no similarity." She married a second time, on 30 November 1722, Thomas WAINWRIGHT. With this marriage, "Troy" passed to her grandson Basil Dorsey, son of Caleb. Thomas died in 1729, leaving Pleasance the greater part of his estate. Pleasance apparently used her wealth to invest in land. A warrant was made out for her 17 December 1717 for 200 acres called "Isle of Ely" adjacent to "Troy". That year she also bought 100 acre "Oldman's Folly". In 1720 she bought 200 acre "Roper's Increase" (perhaps part of the original of which her husband had bought 79 acres in 1705), 50 acre "Howard's Addition", and 120 acre "Poplar Spring Garden" in Baltimore County at the head of the Patapsco River, adjacent to "Howard's Ridge".[30]

"Pleasance died in 1734. Her estate was appraised 14 August 1734, by Benjamin HOWARD and John HAMMOND, son of Charles. Her possessions included some items that had been in her first husband's inventory. Pleasance had wearing apparel, a silver tankard and cups, a silver spoon, thimble, and buckles, 3 silk handkerchiefs, taylor's shears, 2 small punch bowls, 4 ivory handled knives and forks, a pepper box, 1 caster, 1 tin baster, 1 flesh fork, 1 cutting knife and 1 pen knife, 2 chests, a pair of spectacles, 2 "Turkey-workt" chairs, 6 old books (unspecified), furniture and kitchen utensils, stock and feed, one old Negro man named Tom, one old Negro woman named Beck, and one Negro lad named George.[31]

  Death Notes:

1714/15.

  Noted events in his life were:

• Religion: raised a Quaker.

• Surveyed: "Hockley-in-the-Hole," on the south side of the Severn, owned by his father, Edward Darcy, 27 Jan 1664, Anne Arundel, Maryland, (United States). The entire "Hockley" grant may have ultimately consisted of 2,000 acres. It was near the site of Annapolis, on Cabin Neck Brook, a tributary of the Severn River, between Hockley Creek and Underwoods Creek.

• Patented: 400 acres 3 miles from Annapolis called "Hockley-in-the-Hole" with his brothers Edward and Joshua, 20 Aug 1664, Anne Arundel, Maryland, (United States). "Hockley-in-the-Hole" was located on Cabin Neck Brook, which fed Underwoods Creek, a tributary of the Severn.

• Purchased: "Howard's Heirship," 150 acres, from Cornelius and Elizabeth Howard, 4 Aug 1679.

• Purchased: his brother Joshua's right in "Hockley-in-the-Hole," Bef Dec 1681, Anne Arundel, Maryland, (United States). for 8,000 lbs. of tobacco.

• Purchased: his brother Edward's right in "Hockley-in-the-Hole," 6 Dec 1681, Anne Arundel, Maryland, (United States). for 24,000 lbs. of tobacco

• Resurveyed: Hockley plantation, 1683, Anne Arundel, Maryland, (United States). and found it to contain 843 acres instead of the 400 acres first surveyed.

• Purchased: "Dorsey's Adventure," 400 acres on Elk Ridge between the Patuxent and Patapsco rivers, 29 Feb 1688, Baltimore (Howard), Maryland, (United States). This tract, with the one next to it, were called "Patuxent Plantation" and bequeathed to John's grandson, John Dorsey ("Patuxent John" Dorsey).

• Purchased: "Troy," 763 acres on Elk Ridge, 12 Oct 1694, Baltimore (Howard), Maryland, (United States). "Troy" was located between the present towns of Elkridge and Guilford. [It may have been only 736 acres.]

• Purchased: "Dorsey's Search," 479 acres, from James Bayley, 6 Dec 1694, Baltimore (Howard), Maryland, (United States). This estate was on both sides of the north branch of the Patuxent. He bequeathed it to his grandson "Patuxent John" Dorsey.

• Served: as a commissioner for the development of the town and port of Annapolis, 1694, Anne Arundel, Maryland, (United States).

• Served: in the Lower House of the Assembly for Anne Arundel County, from abt 1694 to 1711, Maryland, (United States).

• Served: as Justice of the Peace, 1694, Anne Arundel, Maryland, (United States).

• Residence: on "Troy Hill," by 1695, Anne Arundel (Howard), Maryland, (United States). From http://freepages.genealogy.rootsweb.ancestry.com/~paxson/southern/dorsey.html:
"John commissioned surveyors to 'go beyond Richard Warfield' in upper Anne Arundel County. There on 10 November 1695 he patented 'Troy', 736 acres, between the present towns of Elkridge and Guilford, where he built his home... The tax return of 1695 recorded, 'John Dawsey's Quarter, on Elke Ridge, etc.', so John had a house there by that year. This makes 'Troy' the oldest remaining house in Howard County, although it has been greatly altered. Originally 'Troy' was a one-storey house with a front porch devoid of any ornamentation other than a simple ballustrade. Other floors were added later. The interior and exterior walls were about two feet thick. The old family burial ground was on one side of the house. The front porch now overlooks Meadowridge Cemetery (once part of the Dorsey estate) and route I-95."

• Served: as Justice of the Peace, 1696, Anne Arundel, Maryland, (United States).

• Served: as Captain in the Baltimore County Militia, 1696, Baltimore Co., Maryland, (United States).

• Purchased: "Orphan's Addition" near "Hockley in the Hole," 10 Mar 1697, Anne Arundel, Maryland, (United States).

• Built: his residence "Troy Hill" in his homestead "Troy" on Elk Ridge, by 1699, Baltimore (Howard), Maryland, (United States).

• Moved: to his plantation called "Troy" on Elk Ridge, 1699, Baltimore (Howard), Maryland, (United States).

• Acquired: "South River Quarter," a plantation on the South River: Anne Arundel, Maryland, (United States).

• Purchased: "White Wine and Claret," 1400 acres on the south side of the middle branch of the Patuxent, 6 Jan 1702, Anne Arundel (Howard), Maryland, (United States). The estate was located between the present towns of Simpsonville and Clarksville in Howard County.

• Gave: "Hockley-in-the-Hole" and "Orphan's Addition" to his son Caleb, 6 Aug 1702, Anne Arundel, Maryland, (United States).

• Acquired: "Whitaker's Purchase," 79 acres adjoining "Dorsey's Adventure" on Elk Ridge, 1704, Baltimore (Howard), Maryland, (United States).

• Purchased: "Roper's Increase," 100 acres, from Cornelius and Mary Howard, 14 Feb 1705.

• Purchased: "Mt. Gilboa," 246 acres, 1706.

• Conveyed: "Mt. Gilboa" to Richard Colegate, 1707.

• Served: in the Provincial Council, 1711-1715.

• Served: in the Upper House of the Assembly, From 1711 to 1714, Maryland, (United States).

• Will, 26 Nov 1714, Baltimore Co., Maryland, (United States).

• Probate, 22 Mar 1715.

• Inventory: of his estate was taken by Thomas Hammond and John Israel, 25 Apr 1715, Baltimore Co., Maryland, (United States). Among the holdings were 17 slaves, at least 7 of whom were young children.

• Funeral, 11 Apr 1716.

John married Pleasance Ely, daughter of Edward Ely and Unknown, in 1683 in <Anne Arundel>, Maryland, (United States). (Pleasance Ely was born about 1660 in Maryland, (United States) and died before 14 Aug 1734 in Baltimore Co., Maryland, (United States).)