This post goes from 1687 to 1832 (Joseph’s descendants), but for him the last record is 1725. This post also includes military records.
Here are the Calloway generations, like links in a chain:
JOSEPH → Francis → Samuel → Nancy m. Joel Leakey → Ann S. Leakey m. Thomas Gray → Nancy Margaret m. Amonet Washington Wilbourn → William Harvey → Ella Washington (Rae) (our grandmother)
We have the Callaway Family Association, to help us with the earliest available records:
20 Apr 1687
JOHN MEDOR, 640 acs., Rappa. Co. s side of Rappa. Riv on Beaver Dam SW at head of Hoskins’ Cr. 20 Apr. 1687, p. 558; Beginning on S. side of the old Beaverdam SW, neer [sic] an Indian Path; to a small island &c. 450 acres granted to John Cook 4 May 1659; assigned Thomas Medors 7 Aug. 1659; and granted to him 9 Apr 1664; 190 acs. for trans. of 4 pers: Jno. Chambers, Joseph Calloway, Robert Duell, Jno. Warrener (Nugent 306)
29 April 1693 and 10 Apr 1700
Edmond Andros, working for his majesty, gives and grants unto Jno. Maguffey a patent for 77 acres in Essex County, for importing two persons; property at a corner of a hickory at a branch of Gilson’s Cr., corner of Mr. Edmund (____), west by north by said Paggitt’s line, 440 poles to stake in Old Field, thence north by east of said Tandey’s land, to a corner white oak on Gilson’s main Pocoson, thence by his line to the beginning place; then for 700 pounds of tobacco, John Maguffey assigns over to Joseph Callaway the said patent, 10 April 1700; wit: William Diar, Tho. Hucklescott, John Maguffe (Deeds and Wills 1694-1695, page 30)
10 Apr 1700
This patent was recorded in Essex County Order Book:
John Maguffey acknowledged a deed of assignment of a patent of land to Joseph Callaway, and upon motion of Joseph Callaway the patent assigned to him by John Maguffey is ordered to be recorded (OB 1699-1702, page 30)
10 December 1694
Joseph Collaway witnesses an elaborate deed of gift from John Meador Sr. to his children, in Essex County, South Phernam Parish; Meador’s wife: Elizabeth; sons Richard, John, Thomas, Hope (sic); daughters Rachel Meador, Elizabeth Meador, and Esther Meador; father-in-law Richard White; main property on west side of Great Branch (Deeds and Wills 1694-1695, pages 332-33)
11-12 July 1711
Francis Browning of St. Marie’s Parish, Essex County, to Joseph Calloway of Southfarnham Parish, same county, lease and release, for 2,500 pounds of tobacco, 100 acres, part of a patent granted to Enoch Doughty, decd. on the south side of Portobago Swamp; signed Francis (F) Browning; wit: Henry Byrum, James Graves, and Jno. Ellits; 12 July 1711, acknowledged by Francis Browning; Rachel, wife of Francis, relinquishes her dower rights (Deed and Will Book 13, pages 424-25)
11 July 1711
Bond of Francis Browning of St. Marie’s Parish, Essex County, to Joseph Callaway of Southfarnham Parish, same county, for 5,000 pounds of tobacco, to fulfill covenants in indentures; signed Francis (F) Browning; wit: Henry Byrum, James Graves, and Jno. Ellits; acknowledged 12 July 1711 (Deed and Will Book 13, pp. 424-25)
9 and 10 Apr 1712
Joseph Callaway’s land is mentioned in a lease and release between William Berry and his Mary, of Richmond Co., planter, and Samuel Short, 310 acres in Essex Co., being part of a patent granted to Enoch Doughty, 4763 acres, and bounded by land of Joseph Calloway and Francis Browning, a line running an oak and a pine standing nigh the head of the branch of Matapony; signed William Berry and Margaret Berry; wit: Edward Coleman, Ephraim Paget, and John Boughan (Essex County Deeds and Wills no. 14, page 33)
10 July 1715
Joseph Calloway’s land is mentioned in a deed of gift between Francis Browning of St. Mary’s Parish, Essex County, and his daughter Anne Browning, for natural affection, 100 acres, whereon he now lives, a tract purchased out of tract originally patented to Enoch Doughty; this land adjacent to 100 acres sold to Joseph Calloway and land recently taken up by Jno. Sanders; (unnamed) wife retains her dower rights; signed Francis Browning; wit: Jno. Ellits (sic) and John Morgan (Essex County Deeds and Wills no. 14, page 366)
18-19 Nov 1716
Joseph Callay’s land is mentioned in a lease and release between Sam’l short, planter, St. Mary’s Parish, Essex County and Caleb Lindsey, planter, same parish and county; 310 acres being part of patent granted to Ephraim Douchty for 4763 acres; 3120 acres adj. land of Joseph Callay (sic) and Francis Browning (Fleet vol. II, page 79)
18 Nov 1719
James Calloway of Essex County gets 200 pounds of tobacco for two wolf heads (OB 1716-1719, part II, page 391)
15 Oct 1723
Joseph Callaway get 30 pounds of tobacco for passing one hhd (sic) of tobacco (OB 1723-1725, Part I, page 37)
17 Feb 1724
Joseph Callaway is security for Robert Dudley for being arrested and failing to appear to answer suit of George Tilly in debt; Order is granted against said defendant and Joseph Callaway his security for what shall appear due at next Court unless the defendant appears and answers said action (OB 1723-1725, Part II, page 250)
19 Oct 1725
Joseph Callaway gets 200 hundred pounds of tobacco for two wolf heads by the certificate of Col. John Lomax (OB 1723-1725 Part II, page 339)
These records include many Calloways.
Charles City County
15 July 1661
Thomas Callaway transferred out of Lt. Col. Drewe’s company and added to Maj. William Harris’s company
22 Sep 1756
William Callaway, major; Richard Callaway, Capt.; Francis Callaway, Lt.
3 June 1757
Capt. Richard Calloway, captain of a militia company in Bedford County submits his account, for pay to his company, including £13.9.8 to Capt. William Need, amounting to £159.10.0; it is just
However, some of his account could not be settled, due to a lack of vouchers
James Callaway is mentioned three times or there are three James Callaways, who get their payment: 0.12.0; 2.14.0; 2.14.0
23 Aug 1763
William Callaway, Lt. Col.
29 Feb 1764
James Callaway, Jr. Capt.
17 Oct 1752
Thomas Callaway, Capt.
Thomas Callaway, ensign, get his payment of 0.16.0
Thomas Callaway, Capt. gets his payment of 6.18.0
14 Aug 1756
Sgt. Calliway was not present at Fort Cumberland
Dudley Callaway was part of Capt. Henry Paulling’s Company
Lt. Richard Callaway received payment of £1.4.0
Sgt. Richard Callaway, £0.5.4, for service and provisions
6 Nov 1762
James Callaway petitions government, claiming Indians came into his house and forcibly took a rifle gun valued at £4.0.0 with shot bag, powder horn, and snaffle bag valued at 7.6.0
11 Nov 1762
Petition of James Callaway rejected
Zachariah Callaway, for pay as Armourer and Assistant on Cherokee Expedition: 20.10
For Gun Locks account and certificate £1.8
5 Jan 1778
Richard Callaway for service in the Kentucky Militia, 28.7.10
14 Aug 1832
I Dudley Callaway of the Town of Lynchburg in the C. of Campbell and State of Va. do hereby certify & do solemnly swear – that I enlisted a Soldier in the Army of the Revolution in the year 1776 and served in the 5th Regiment of the Va. line for 16 months, when he [William Dewes] was detached from said 5th Regt. & put under the Command of Col. Daniel Morgan who commanded a rifle choir and served with said Morgan that he the said Wm Dewes was also detached from 9th Regt. & and was put under Col. Morgan and served with me under said Morgan several months, when he was put back with said Col. Matthews of the said 9th Regt. – and I was informed that said Dewes was in Battle of Germantown & taken prisoner by the British & kept several months – that I believe the said Wm Dewes enlisted for two years and served faithfully as soldier in the Army of the Revolution, Given under my hand and seal this 14th Day of Aug 1832
Lloyd DeWitt Bockstruck, Virginia’s Colonial Soldiers, Baltimore: Genealogical Publishing, 1988.
John Frederick Dorman, Essex County, Virginia, Deeds and Wills, 1707-1711, no. 13, Washington, D.C.: privately published, 1963.
Beverly Fleet, Virginia Colonial Abstracts, vol. II, Baltimore: Genealogical Publishing, 1988.
—, Virginia Colonial Abstracts, vol. III, 1711-1714, Greenville, SC: Southern Historical P, rpr. of 1940.
—, Virginia Colonial Abstracts, vol. IX, 1714-1717, Essex County Wills and Deeds (n. p. n. d.)
Nell Marion Nugent, Cavaliers and Pioneers: Abstracts of Virginia Patents and Grants, vol. 2, 1666-1695, Richmond: Virginia State Library, 1977.
Ruth and Sam Sparacio, Virginia County Court Records: Order Book Abstracts of Essex County, Virginia 1723-1725 (Part I), Mclean, Virginia, Antient P, 1989.
—, Virginia County Court Records: Order Book Abstracts of Essex County, Virginia 1723-1725 (Part II), Mclean, Virginia, Antient P, 1989
—-, Virginia County Court Records: Order Book Abstracts of Essex County, Virginia 1716-1723 (Part II), Mclean, Virginia: Antient P, 1990.
—, Virginia County Court Records: Record Abstracts of Essex County, Virginia, 1694-1695, McLean, Virginia: Antient P, 1991.
—, Virginia County Court Records: Deed and Will Abstracts of Essex County, Virginia, 1699-1700, McLean, Virginia: Antient P, 1991.
—, Virginia County Court Records: Order Book Abstracts of Essex County, Virginia, 1699-1702, Mclean, Virginia: Antient P, 1991.
Virginia Military Records from the Virginia Magazine of History and Biography, the William and Mary College Quarterly, and Tyler’s Quarterly, Baltimore: Genealogical Publishing, 1983.