[1] Two decades later, Bennett immigrated to the Maryland colony with his family, and settled on the Severn River in Anne Arundel County.
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".
[citation needed] 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.
[10][11] 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".
From 1651 until 1657-8, Bennett held a parliamentary commission for Virginia, during which time (in 1655 as discussed below) he returned to England to oppose Lord Baltimore's claim to Maryland.
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.
[13] 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.
In 1667 Bennett led English colonial forces against a four vessel Dutch fleet marauding through the Hampton Roads area.
The Wicomico County, Maryland house built by the next owner of Bennett's Adventure in the eighteenth century still stands, and in 1975 was listed on the National Register of Historic Places.