See The Bowles of Deal Family Tree

There has been much confusion over this line, partly due to the family historian WH Bowles mixing up Valentine II with a son of Charles Bowles of Chatham (~1610-1659, who gathered a vast fortune during the Commonwealth as Commissary for Kent), and because some of the family later settled in Maryland, where there are many Kent place names, but no Deal. The best evidence is from the Register of St Margaret’s Rochester, where a William Bowles was baptized on 1^st October 1641, the son of Valentine Bowles I and his wife Frances. Rochester and Chatham are neighbouring Kent towns on the Thames Estuary – Rochester sits at the top of the hill with the Cathedral, leaving Chatham with the dockyards down below. Charles Bowles of Chatham was also living in Rochester in 1641, and there is certainly a close family connection between Charles and Valentine I to uncover (brothers or cousins?) – both lines use the name Phineas for example. Several of Valentine II’s children served as officers in the Royal Navy, suggesting the patronage of Charles’s son Phineas, who was high up in the service becoming Secretary after Samuel Pepys in 1689. There was a Valentine Bowles from Somerset, a Vintner living in Bow and Essex, but his 1637 Will mentions no sons, and no connection has been established.

Valentine II was a grocer in Deal, which was a thriving community servicing ships anchored in the lea of the Downs awaiting favourable winds. He was also a Quaker, spending 5 months in prison in 1684 for refusing the Oath of Allegiance, and the births of many of his children are recorded in the Monthly Meeting books. William Penn’s tour of Kent in 1672 (unpublished Journal and spelling erratic) records a visit to Deal where “one Valentine Brooks a notable wise man is there convinced”. His Will of 1710 is a lengthy document, and he was clearly not on trusting terms with all his family on his death! George “has laid too much useless money upon the house which I wish were as when he took it, and also made a shop next my conduit to little purpose”, while Jane had given credit to customers and “ought to bear the loss because she would trust many against my will”, whereas Valentine III “shall not have his part in his possession or disposal, but to have settled on him £16 or £18 pounds a year out of my estate”. His children appear not to have been Quakers.

The eldest son, Tobias, was a wealthy tobacco merchant trading with Virginia, which he visited several times. Tobias was active in politics, securing a Town Charter for Deal in 1699 (which had previously been under the control of Sandwich), serving as Mayor, and petitioning the Government on aspects of trade with the Colonies. In 1709, he was suggested as Governor of Maryland (after the death of Charles Bowles’s son-in-law, John Seymour), but this was not pursued. His son James settled in St Mary’s County, Maryland in 1699, buying 2,000 acres and building a house at Sotterley Plantation in 1703 which still stands (much extended) today. Valentine III was Captain of HMS Sheerness, and dismissed after a court-martial in 1698 for drunkenness and neglect of duty while stationed in the West Indies!

John and George (and possibly Valentine III, IV or V?) settled in Maryland after their father’s death. There are a number of puzzles in the Maryland line. Clearanna Bowles, claimed to be a daughter of Valentine, is born ~1675 in USA and marries William Billingsley ~1690. The Billingsley’s were Quakers, but there is no obvious link to Valentine I, II or III. George Bowles is reported (Mary Louise Donnelly, no sources) to have had children in the USA, but there is no evidence of their birth, and the Wills of George, his wife and John do not name any descendents.