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clined); 1st Council of Safety, Eastern Shore, 1775;
chancellor, appointed 1777 (declined). LOCAL OF-
FICES: sheriff, Queen Anne's County, 1745-1748.
WEALTH DURING LIFETIME. PERSONAL PROP-
ERTY: assessed value £2,690.0.0, including 56
slaves and 365 oz. plate, 1783. LAND AT FIRST
ELECTION: 114 acres in Queen Anne's County (96
acres as a gift from his father; 18 acres by pur-
chase). SIGNIFICANT CHANGES IN LAND BE-
TWEEN FIRST ELECTION AND DEATH: purchased
134 acres in Queen Anne's County, 1753; accord-
ing to the terms of his father's will, James's
mother held a life estate in 1,440 acres in Queen
Anne's County. When she died in 1755, James and
his brother Henry Hollyday (ca. 1725-1789) inher-
ited the land, with James's portion being 840
acres. WEALTH AT DEATH. DIED: will probated on
November 16, 1786, in Queen Anne's County.
Hollyday died from malaria, a disease he had suf-
fered from for years; buried at his home "Read-
bourne Rectified." PERSONAL PROPERTY: re-
quested no appraisal of his estate; left legacies of
over £2,000 current money. LAND. 1,088 acres in
Queen Anne's County, plus 1 lot in Chestertown,
Kent County, and 1 lot in Havre de Grace, Har-
ford County. ADDITIONAL COMMENTS: his princi-
pal heir was his brother Henry Hollyday (ca. 1725-
1789).
HOLLYDAY (HOLLADAY, HOLLIDAY),
JAMES (1758-1807). BORN: on November 1,
1758, probably in Talbot County; eldest surviving
son. NATIVE: fourth generation. RESIDED: spent
much of his early life with his uncle James Holly-
day( 1722-1786); at "Readbourne," Queen Anne's
County, 1779 until death. FAMILY BACKGROUND.
FATHER: Henry Hollyday (ca. 1725-1789), son of
James Hollyday (1696-1747). MOTHER: Anna Ma-
ria (ca. 1732-1804), daughter of George Robins
(1697-1742). UNCLE: James Hollyday( 1722-1786).
HALF UNCLES: Richard Lloyd (1717-1786); Ed-
ward Lloyd (1711-1770). AUNTS: Margaret Robins
(1734-1808), who married William Hayward (1-
1791); Henrietta Maria Robins (1736-1791), who
married James Lloyd Chamberlaine (1732-1783).
BROTHERS: Henry, who died at age two; Thomas
(1760-1823); and Henry (1771-1850). SISTERS:
Henrietta Maria (1750-1832), who married Sam-
uel Chamberlaine (1742-1811); Sarah (1753-
1829); Anna Maria (1756-1817), who married
George Gale (1756-1815); Rebecca (1762-1801),
who married Nicholas Hammond (1758-1830);
Elizabeth (1768-1810); and Margaret (1774-?).
FIRST COUSIN: Henrietta Maria Chamberlaine (?-
1804), who married William Hayward, Jr. (ca.
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1758-1834). MARRIED in 1790 Susanna (Susan)
(1774-1849), daughter of James Tilghman (1743-
1809); granddaughter of George Steuart (1700-ca.
1784); niece of Peregrine Tilghman (ca. 1741-
1807). Her brothers were George (1771-1792);
Frisby (1773-1847). CHILDREN. SONS: James
(1792-1832), who went to Louisiana and lost his
entire fortune; Henry (1798-1865), who married in
1826 his first cousin Anna Maria Hollyday;
George Steuart (1799-1870), who served in the
Maryland legislature ca. 1842, and who married in
1825 Caroline Matilda Carvill; Frisby (1801-
1821), who went to sea and died of yellow fever;
William (1804-1868), who married first, in 1830
Ann Cheston Tilghman (?-1834), and second, in
1837 Louisa Lamar Tilghman, his first wife's half
sister; and Richard Tilghman (1806-?), who mar-
ried Susan Regan. DAUGHTER: Anna Maria Chew
(1796-1823), who married Arthur Tilghman
Jones. PRIVATE CAREER. EDUCATION: received his
early education at the Talbot County Free School.
He later entered the Kent County Free School and
completed his academic courses when that school
became Washington College in 1782; studied law
first with his uncle James Hollyday (1722-1786),
and later under Thomas Bedingfield Hands (?-
1811). SOCIAL STATUS AND ACTIVITIES: Esq.,
1798; fourth generation legislator. OCCUPATIONAL
PROFILE: lawyer. PUBLIC CAREER. LEGISLATIVE
SERVICE: Lower House, Queen Anne's County,
1788; Senate, Eastern Shore, Term of 1791-1796:
1791-1792, 1792, 1793, 1794 (did not serve), 1795
(did not serve), Term of 1796-1801: 1796, 1797
(did not serve), 1798, 1799 (did not serve), 1800.
OTHER STATE OFFICE: Constitution Ratification
Convention, Queen Anne's County, 1788. LOCAL
OFFICE: associate justice, Second District, Queen
Anne's County, appointed January 1791, resigned
by October 1791. MILITARY SERVICE: assigned to
a company of horse, 1777; lieutenant, Queen An-
ne's County Militia, by 1794; captain, by 1799.
WEALTH DURING LIFETIME. PERSONAL PROP-
ERTY, inherited 18 slaves from his father and all of
the law books of his uncle James Hollyday (1722-
1786), 1789; from ca. 1791 until his death, James
controlled the estate of his brother Thomas, who
suffered from mental illness and lived with him; 42
slaves, 1798; held stock in the Havre de Grace
Company, 1804. LAND AT FIRST ELECTION: 1,088
acres in Queen Anne's County, 1789. This land
belonged to his uncle James Hollyday (1722-1786),
with whom he lived from 1779, but he did not re-
ceive actual title to the property until his own fa-
ther's death in 1789. Managed the 598 acres in
Queen Anne's County that belonged to his brother
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