Career
After assuming management of his uncle's Virginia business interests and taking his seat in the House of Burgesses in 1629, Richard rose to prominence in the business, political, and religious life of the colony. He became leader of the small Puritan community south of the James River, taking them from Warrasquyoake to the drainage of the Nansemond River beginning in 1635. Warrasquyoake was renamed as Isle of Wight County in 1637 and Nansemond County was formally split from Isle of Wight county in 1646.
Governor Francis Wyatt with the consent of the Crown in London appointed Bennett as a member of the Governor's Council in 1639–42, and he would intermittently serve in what was the colony's upper house (and highest court) for the rest of his life, albeit with interruptions during an unstable era. In 1646, near the beginning of the English Civil War, Puritans from Nansemond formed part of the force sent by Virginia Governor William Berkeley to restore order in Maryland after the "Plundering Time".
In 1648, under political and religious pressure during the English Civil War, and upon the invitation of new Maryland governor William Stone of Hungers Creek, Bennett became one of the leaders of the Virginia Puritans who received a grant from Lord Baltimore and established a settlement on the Severn River in Anne Arundel County, Maryland. There, Bennett received at least one land grant of 250 acres on the banks of the Severn River near the Broadneck Peninsula known as the Towne Neck or later Greenberry Point, and returned to Virginia for settlers on what they called "Providence". He subsequently received two large grants of 1150 and 1250 acres called Upper Bennett and Lower Bennett on the Cliffs of Patuxent, upon which he settled associates from Nansemond. From 1651 until 1657-8, Bennett held a parliamentary commission for Virginia and worked with William Claiborne to annex Maryland to Virginia. During this time (especially in 1655 as discussed below) Bennett returned to England to oppose Lord Baltimore's claim to Maryland.
Meanwhile, Virginia Governor William Berkeley, who had been appointed in 1641, was sympathetic to the Crown during the English Civil War. Sir William Berkeley even fought for the deposed King Charles before returning to Virginia to quell raids by Native Americans on the relatively young colony. But on 12 March 1652, in a negotiation partly arranged by Bennett, Berkeley surrendered to representatives of Cromwell's Commonwealth government when they arrived in Virginia, and the colony's secretary Mathew Kemp became Virginia's acting governor.
The Virginia House of Burgesses then unanimously elected Bennett, who had returned to Virginia, as that colony's governor on 30 April 1652. Much of Bennett's time as governor involved negotiations both on behalf of the two colonies with officials in England, and with Native Americans. He negotiated with the Susquehannock tribe (which spoke an Iroquoian language) and signed a treaty with them on 5 July 1652. Under this, they ceded their claims to "all the land lying from the Patuxent River unto Palmer's Island on the western side of the bay of Chesapeake, and from the Choptank River to the northeast branch which lies to the northward of Elk River on the eastern side of the bay." Some of this area continued to be claimed by the Nanticoke tribe, however, which was an Algonquian-speaking tribe, with a different culture.
On 30 March 1655, Bennett voluntarily abandoned his Virginia office (the House of Burgesses electing fellow planter Edward Digges governor in his stead), and sailed for England to see Oliver Cromwell. He was back in London on 30 November 1657 when he signed the treaty with Cecilius Calvert, 2nd Baron Baltimore, which recognized the latter's claim to Maryland. Back in Virginia, Bennett again attended the Governor's Council and was later commissioned as a major-general in that colony's militia.
In 1665, his son, Richard Bennett Jr., who represented Baltimore County in Maryland's Assembly patented 2500 acres on the north bank of Wicomico Creek, on Maryland's Eastern Shore, in what is now Wicomico County. The plantation became known as Bennett's Adventure.
In 1667 Bennett led English colonial forces against a four vessel Dutch fleet marauding through the Hampton Roads area.
In early 1671, George Fox, founder of the Quaker movement, who had been released from Scarborough Castle in Yorkshire in 1666, set sail for the American colonies. He initially landed in Jamaica, then visited Barbados (the wealthiest colony in that era) before setting sail for Maryland. There Fox attended the First General Meeting of Friends at West River in Anne Arundel County in April 1672. After Fox journeyed to The Cliffs in Calvert County, he, missionary John Burnyears, Robert Widders and George Patterson sailed for the Eastern Shore (where they set up what became the Third Haven Meeting at Easton), while sending John Cartwright and James Lancaster to New England, and William Edmundson and others to visit Virginia Puritans in Nansemond County. Fox preached and planted Meetings in many areas, especially around Chesapeake Bay, and met the Speaker of the Maryland Assembly (Samuel Chew, who with his wife Ann Ayres were ardent Quakers) as well as two members of the Maryland Governor's Council and a persecuted justice from the Potomac area of Virginia, before returning to England from the Patuxent Roads area two years after he had left. Accounts differ as to whether Edmundson or Fox himself converted Bennett to his faith.
