On October 25, 1792, Lee County was formed from Russell County. The County was named for "Light Horse" Harry Lee, a noted Revolutionary War officer and governor of Virginia from 1791-1794.

On November 17, 1792, the Virginia Legislature passed an Act requesting Charles Cox and others to help find a wagon road through Russell County.  On December 10, 1792, Charles Cox was named one of the Justices for Lee County, along with Joshua Ewing, William Ewing, William Neal, Charles Carter, Isaac Chrisman, John Hunter and George Gibson.

In 1794, Charles sold 76 acres on Indian Creek to Alexander Stewart. In 1795, Charles Cox is listed in the Lee County Personal Property Tax List. In 1797, Charles sold 300 acres on Trading Creek to James Burgan. In 1798, Charles and Elenor Cocke deeded 200 acres on Indian Creek to John Cocke for 150 pounds. John is likely their son, who was mentioned in the Will of John Ewing.

From 1795 to 1800, Colonel Charles Cocke served in the Virginia Legislature, as representative of Lee County. Gabriel Chrisman, who is a likely son in law of Charles Cocke, also served in the Virginia legislature from Lee County in 1797. In 1800, Charles Cocke shows up in the Tax List for Lee County. In 1802 and 1803, Charles Cocke appears on the Tax List for Lee County and is shown as owning 740 acres. In his diary, Governor John Sevier of Tennessee mentions spending the night at Colo. Charles Cocks house on the night of 6 Dec 1802.

Charles apparently moved to Wayne County, KY in the last part of 1803. On 29 Feb 1804, an indenture is recorded showing that Charles and Ellender sold 510 acres on both sides of Indian Creek to Robert Beatty. Interestingly, the deed is recorded in Wayne County, KY. In 1806, an indenture is recorded showing that Charles sold an additional 170 acres in Lee County to Samuel and Jane Priest. This indenture is recorded in Lee County.

An act to facilitate the intercourse of the inhabitants of this Commonwealth with the State of Kentucky:
(Passed November 17, 1792)
Preamble Sect. 1. Whereas it is represented to the present General Assembly, that opening a waggon road from the blockhouse in the western extremity of Washington County, to the top of Cumberland Mountain, in the county of Russell being where the road from the state of Kentucky terminates, will be of great public utility in facilitating the intercourse from the extreme southwest parts of this state with our eastern brethren at the seaport towns, and as the same, on account to the length of the way and the many difficulties attending the opening thereof, cannot be cleared by the ordinary method prescribed for opening roads; and as this Assembly are at all times willing to contribute every encouragement to such designs as are represented to be of general utility, as far as is consistent with prudence and good economy. Commisioners to view and mark a way for a road from the blockhouse in Washington to the top of Cumberland mountain. Their report to be made to the next Assembly.
Sect. 2, Be it enacted, That William Tate, John Anderson, Charles Cox, Walter Preston, James Fulkerson, Thomas Berry, and Thomas Wallen, gentlemen be, and they are hereby appointed commisioners, to explore, view, and mark out the best and most eligible way for a waggon road, from the said block-house, in the county of Washington, to the top of Cumberland mountain, in the said county of Russell, and to report to the next General Assembly, their opinion, with respect to the practicability of said road, the distance between the said places, and also an estimate of the expence which would necessarily be incurred in opening a waggon road as aforesaid.

On December 10, 1792, Charles Cox was named one of the Justices for Lee County, along with Joshua Ewing, William Ewing, William Neal, Charles Carter, Isaac Chrisman, John Hunter and George Gibson.

The following lawsuits are mentioned in the Court records:
p. 55 Charles Cocke vs. Hatfield, continued Jan 1793
p. 58 Charles Cocke vs. George Hatfield, continued Feb 1793
p. 64 Charles Cocke vs. John Hatfield, continued 24 Apr 1793
p. 87 Charles Cocke vs. George Hatfield, continued Jul 1793
p.116 Charles Cocke vs. George Hatfield, continued Oct 1793
p.124 Chas. Cocke vs. George Hatfield, continued Nov 1793

Indenture 11 June 1793, Charles & Elenor Cocke Lee Co. Va. sell to Gabriel Chrisman and his heirs for 20 shillings 400 acres S.W. at foot of Wallings Ridge.
Charles Cocke
Elender Cocke
11 June 1793 to Gabriel Chrisman
Teste: Charles Clark, Esq.
[Obtained 17 Feb 1783?]

11 June 1793 between Charles Cocke & Ellender, his wife, of Lee Co. Va. & Samuel Adams. For sum of 21 pounds & six shellings sell to Samuel Adams & his heirs 213 acres in Lee Co.
Charles Cocke
Ellender Cocke
10 September 1793 Teste: C. Carter Esq.
[Deed Book 1-4]
[Obtained 6 Jan 1786?]

Indenture 10 Sept. 1793 between Charles Cocke & Ellinder, his wife & James Trotter, all of Lee Co., Va. for $100 216 acres in Lee Co. waters of Trading Creeks to John Trotter and his heirs.
Charles Cocke
Ellender Cocke
10 Sept. 1793 Teste: Charles Carlen, Esq.
[Obtained 6 Jan 1786?]

10 Sept. 1793 between Charles Cocke & Ellender, his wife, of Lee Co. Va. & James Trotter for $100 paid by James Trotter for 400 acres in Lee Co. for Samuel Trotter & his heirs.
10 Sept. 1793
Charles Cocke
Ellender Cocke
10 September 1793 Teste: C. Carter, Esq.

Indenture 14 Jan. 1794 Charles and Elleonor & Alexander Steward for 16 pds for 76 acres in Powells Valley
Charl. Cocke
Ellinder Cocke
14 January 1794 Teste: C. Carter CLC.
[Obtained 26 Mar 1791?]

Indenture 15 January 1794 Charles & Ellender Cocke to Samuel Priest, all of Lee Co. Va. for 25 pds. 120 acres in Powells Valley to top of Poor Valley Ridge to corner of Elizabeth Prust and Aleseander Stewart.
Signed: Samuel Priest his heirs.
Charles Cocke
Elender Cocke
Teste: C. Carter, Esq.

An Act for opening a wagon road from the Block House (Moccasin Gap) in Washington County to the Cumberland mountain in the County of Lee (Passed December 18, 1794). Commissioners appointed.
1. Be it enacted by the General Assembly That Charles Cocke, Benjamin Sharp, William Ewing, William Neil and Frederick Jones, gentlemen, or any three of them, be, and they are hereby empowered and required to contract and agree with such person or persons as they may judge most proper for opening and clearing a wagon road from Big Mocason Gap to Benedict Eries [Yeary's] in the County of Lee, as the same hath been marked out by the commissioners appointed by an act of assembley, passed in the year one thousand seven hundred and ninety-two, instituted, "An Act to facilitate the intercourse of the inhabitants of this commonwealth with the State of Kentucky."

Benjamin Sharp and Hannah his wife to Charles Cocke, William Neall. Authority to take acknowledgement of Hannah Sharp.

Representatives from Lee County:

[Charles Cocke] was "a rough back woodsman, a good hunter and Indian fighter [who, although he] had a great deal of common sense [was] destitute of the knowledge of letters." He nevertheless won election to the Virginia Assembly. And when time came for the delegates to "sign their names to the role," his acquaintance and fellow legislator General Joseph Martin went with him, signed his own name and told Cock, "as I have the pen in my hand, I will sign your name."

Gabriel Chrisman, 400 acres
Isaac Chrisman, 400 acres
Charles Cocke, 740 acres
Joshua Ewing, 300 acres
William Ewing, 1655 acres

Joseph Morton of Oglethorpe Co., Ga. appoint William Thornton Morton of Rockingham N.C. power of atty to convey tract of land to John Lewis of Lee Co. Va. and to receive of Charles Cox of same county and state sum of due money and revoke Marbel Stone.
1 July 1796
Joseph Morton [seal]
13 Sept 1796
Test C Carter CLC

Representatives from Lee County:

Gabriel Chrisman, 400 acres
Isaac Chrisman, 400 acres
Charles Cocke, 740 acres
Joshua Ewing, 300 acres
William Ewing, 835 acres

Indenture 6 Oct 1797 between Charles & Eleanor Cocke and James Burgan, all of Lee Co Va., for sum of 60 pds for 300 acres, by grant 14 Oct 1795. Affix seals.
Charles Cocke [seal]
Eleanor Cocke [seal]
[Note: "James Burgin , who married Mary McCarty came to Lee Co. in 1796 or early 1797. On Oct. 6, 1797, he purchased 300 acres from Charles and Eleanor Cocke. Recorded in Deed Book 1, page 77." [Early Settlers of Lee County, Virginia, p. 187]]

Indenture 11 Oct 1797 between Charles & Eleanor Cocke and James Trotter, both of Lee Co Va., for 7 pds for 66 acres beginning at corner of James Burgens. Affix seals.
Charles Cocke [seal]
Eleanor Cocke [seal]
10 Oct 1797
Test. Saml. Ewing D.C.

Representatives from Lee County:

Gabriel Chrisman, 400 acres
Isaac Chrisman, 400 acres
Charles Cocke, 740 acres
Joshua Ewing, 500 acres
William Ewing, 1655 acres

Know all men by these presents that I [Col?] Charles Cocke of the State of Virginia and County of Lee, Inn Holder for the natural love and affection that I have unto to John Stephenson senr of the County aforesaid do grant ___ and Let unto the said Stephenson a certain tract containing fifty acres be the same more or less, lying on the South side of Indian Creek adjoining and lying on the east side of the mill branch will all and singular the woods waters water courses profits commodities, heridataments and appurtenances whatsovere to the said tract of Land belonging or appurtaining and I the said Cocke do warrant the said Tract of Land against all and every person or persons Claiming the said Land premesis for the use and behoof of the said John Stephenson for and during his natural life for the consideration of one bushel of corn to be paid by the said Stephenson unto the said Cock and a the expiration of said time which shall be at the decease of said Stephenson, his legal representative shall deliver up the said premises to the said Charles Cocke or his representatives.
Given under my hand and Seal dated the 25th day of March 1798.
Charles Cocke [seal]
At a Court held for Lee the 10th day of April 1798 This lease was proven in Court and ordered to be recorded.
Test
Saml. Erving [Ewing] D.C.

Indenture 9 April 1798 between Charles Cocke and Isaac Mullen, both of Lee Co Va., for sum of 100 pds for 154 acres. Affix seals.
Charles Cocke [seal]
Elenor Cocke [seal]
10 April 1798
Test. Saml. Erving [Ewing] D.C.

Indenture 10 March 1798 between Charles Cocke and Michael Gibbs, both of Lee Co Va., for land containing 222 acres to corner of Isaac Mullens. Affix seals.
Charles Cocke [seal]
Elinor Cocke [seal]
10 April 1798
Test. Saml. Erving [Ewing] D.C.

Indenture 7 March 1798 between Charles Cocke and Robert Butcher, both of Lee Co Va., for sum $250 for land containing 182 acres to lines of Alexander Stuart & Isaac Mullens land. Affix seals.
Charles Cocke [seal]
Elenor Cocke [seal]
10 April 1798
Test. Saml. Erving [Ewing] D.C.

Indenture 2 April 1798 between Charles Cocke and John Cocke, both of Lee Co., Va., for sum of 150 pds for land containing 200 acres on Indian Creek. Affix seals.
Charles Cocke [seal]
Ellenor Cocke [seal]
10 April 1798
Test. Saml. Erving [Ewing] D.C.

Representatives from Lee County:

Isaac Chrisman, 400 acres [p. 1]
Charles Cocke, 740 acres [p. 1]
Gabriel Chrisman, 400 acres [p. 1]
William Ewing, 100 acres [p. 2]
Joshua Ewing, 300 acres [p. 2]
Jester Cocke, 100 acres [p. 3]
Samuel Ewing, 150 acres [p. 4]

Charles Cocks, 740 acres
Gabriel Chrisman, 800 acres
William Ewing, 1555 acres
Joshua Ewing, 300 acres
Jester Cocks, 100 acres
Isaac Chrisman, 400 acres

Indenture 15 Sept 1802 between Isaac & Mary Mullen and Jacob Crabtree of Lee Co. VA. for $1000 for 154 acres, more or less, and 22 poles, part of tract of land claimed by Charles Cocke. Affix seals.
Isaac Mullen {seal}
Mary Mullen {seal}
14 June 1803
Teste Charles Carter C.L.C.

Isaac Chrisman, 400 acres
Charles Cocks, 740 acres
Gabriel Chrisman, 400 acres
William Ewing, 1555 acres
Joshua Ewing, 300 acres
Jester Cocks, 100 acres

Indenture Charles Cocke and his wife Ellender of Wayne County to Robert Beatty of Lee County, VA $3000 for 510 acres in Lee County on both sides of Indian Creek, a N branch of Powells River. Beginning by a dry branch to land of (?) .... John Cocke's land, signed Charles Cocke and Ellender Cocke, witness Micah Taul.

Indenture 10 Oct 1806 between Samuel & Jane Priest, Wayne Co. Ky. and Charles Cocke of same co. for sum of 70 pds for 170 acres in Lee Co. Va. and Powels Valley. Land to corners of land of Elizabeth Priest and Elixander Stuart. Affix seals.
Samuel (his mark) Priest [seal]
Jean (her mark) Priest [seal]
Wayne Co. Ky. I, Michah True, clerk of co. Court do certify proof of deeds 10 Oct. 1806 and wife Jane Priest examined privately and relinquished right of dower. Set my private seal (no public seal being provided)
Micah True
Wayne Co. Ky., I, Edward N. Cullom, J.P. state above in due form. Seal 31 Oct 1806.
Edward N. Cullom, J.P.
[Obtained 5 May 1791?]

John Cocke, 200 acres
William Ewing
Joshua Ewing
Samuel Ewing