On 29 Jan 1620/1, Sir Francis wyatt was elected Governor and Captain General of Virginia Colony at a court of the London Company, When he arrivedin Virginia in Oct 1621, he was accompanied by William Clayborne who had been appointed Surveyor-General. In 1626, when Sir George Yeardley was re-appointed Governor of the Colony, Clayborne was appointed its secretary of state and became a member of the Governor's Royal Council. The following year, the Governor directed Clayborne to explore the Chesapeake Bay, and one year later, in 1627, he was granted a license to trade “in those parts of America for which there is not already a patent granted to others for the sole trade.” Clayborne established his post on the Isle of Kent, and in 1631, he and the Rev. Richard Jones (Church of England) began to settle the island.

On 20 Jun 1632, however, the Isle of Kent was included in the boundaries described in the charter for the new province of Maryland granted by Charles I to Lord Baltimore (Calvert). When Clayborne resisted Lord Baltimore's claim to the island, the proprietor ordered his brother, Leonard Calvert, Governor of Maryland, to seize the settlement, and it was following this dispute that new Virginia Governor John Harvey deposed Clayborne as Secretary of State. The Isle of Kent nevertheless remained a Protestant bastion and a thorn in the side of Maryland for many years to come.

No complete lists of all inhabitants of the Isle of Kent, but the following is a list of freemen in 1638:

Know all men by these presents both present and to Come that we the freemen of the Isle of Kent whose names are hereunder written have elected and chosen our Loving Friend Nicholas Brown Planter to be our Burgess or deputy during the next General Assembly at Saint Marys summoned to Begin on the 25th. of February next in Our names to assent to all and only such things as our Burgess shall think fit thereby Giving as free and full Consent unto all Laws and matters whatsoever within the said Assembly shall be agreed and Concluded of as if we our selves in person had Consented thereunto

In witness whereof we have hereunto sett our hands this 18th. february 1638

Thomas Allen	Thomas Hales
John Smith	Edmond Parry
William Medcalfe	John Thompson
Philip Conner	Robert Cooper
Walter Weebs	Henry Huett
John Parry	Henry Crawley
Dieck Genitz	Thomas Ewell
Roger Bayster	Henry Bellamie
John Abbott	William Risbrooke
Matthew Price	Walter Cottrel
Thomas Woolfe	Richard Browne
John Glantham	John Bennett

(Liber M C, p. pp. 39-40, Assembly Proceedings, February--March 1638 /9. 31, Archives of Maryland, Vol. I)

In 1652, William Clayborne and Richard Bennett (a Puritan from Nansemond County, Virginia) were appointed Parliamentary Commissioners over both Virginia and Maryland by the new Commonwealth of England Following the execution of Charles I in 1649, Maryland, not surprisingly, remained steadfastly Royalist, but for once she and Virginia were on the same side of the fence, as Virginia, too, continued to favor the monarchy (a considerable number of Royalists having removed to that Colony during the Civil War). Clayborne moved swiftly, and on the 5th of April 1652, the following petition was signed:

Isle of Kent 5th April 1652: We, whose names are hereafter subscribed, do promise and engage ourselves to be true and faithful to the Commonwealth of England, without King or House of Lords.

Thomas Ward
Thomas South
Tho. Wetherell
Tho. Pett
Tho. Taylor
Hen. Carlyen
John Hud
Robert Martin
John Smith
Henry Ashley
John Philips
John Gould
Edw. Ebes
John Smyth
John Richeson
Hen. Taylor
Will Leedes
John Sepsen
Anthony Calliway
Robert Vaughan
Philip Commins
Thos. Ringgould,
Thos. Bradnox
Hen. Morgan
William Elliott
Robert Halters
Richard Blunt
Matthew Read
Will Jones
John Ringgold
Francis Bright
Edw. Copedge
Edmt. Weebe
John Russell
Rich. Salter
Marke Benton
Will Band
Francis Barnes
Hen. Clay
Roger Baxter
James Horner
Hen. Weest
Isa. Ilive
George Croutch
Edward Burton
Abraham Hollman
John Winchester
Nicholas Picurd
Nic. Browne
David Geldersen
Will Price
Tho. Hill
John Dean
Edw. Coxe
Robert Dun
Fran Lumbard
John Gibson
John Maconick
Thomas Weest
Joseph Wickes
John Coursey
John Errickson
Andrew Hanson
Andrew Anderson

To ye truth of this I here subscribe