I find Roger Preston in VA in the 1620's, then in New England where he died 1638. Then I find Richard Preston coming to VA then moving to MD where he died 1669.My guess is Roger had land in VA and Richard came to VA for that land. (Richard being a son of Roger). After Richard died there were other Prestons that came to MD. John,Thomas, and Ralph came in 1776. Edward went to Barbados in 1679, then a Edward goes to VA in 1726. In 1774 Edward Preston, age 38, a baker, came to MD from London. I also found several Prestons in Bedford Co, VA starting before 1800. George Bowles Sr was from Bedford Co before Franklin Co, VA. Leathel, 16 Sep 1669 - 08 Jan 1669 (Calvert Co MD Wills 1:357) The Last Will and Testament of Richard PRESTON, dated 16 Sep 1669, proved 8 Jan 1669/70, Calvert County, MD, includes: to Thomas PRESTON," Upon the Clifts." to Isaac HUNT and grandchild. William and James BERRY, personalty. To son James PRESTON, if living, use of home plantation until grandson Samuel PRESTON attains age of 21 yrs.; daughter in law Margaret PRESTON to have charge of her son, sd. Samuel, during minority. To son James, "Barren Island," on Eastern Shore. To daus. Rebecca and Sarah PRESTON, equally, 600 Acres by patent. In event of death of both daughters without issue, sd. patent to pass to son James, if living. In event of his death to pass to kinsmen James and John DORSEY, or DARSEY. To Kinsman Ralph DORSEY, certain land on little Choptank River. To 3 child. of Testator, James, Rebecca, and Sarah PRESTON, residue of estate equally. Ex. not named. Test Enoch COOMES, Geo. DUELIN, Thomas PEAKE, William JONES. 1.357 (Maryland Calendar of Wills, Cotton, Vol. 1, p. 50) A more detailed and slightly different abstract of this will has been extracted by Combs Researcher Birdie McNutt from "American Wills Proved in Londaon 1611-1775", compiled by Peter Wilson Coldham, Genealogical Publishing Co., Inc., Baltimore, MD, Copyright ©1992 by Peter Wilson Coldham Surrey, England, Page 23: Will of Richard PRESTON of Patuxent, MD., dated 2 Dec. 1699 [nb: 1669]. To my son James PRESTON, if he is alive and returns from England to Md., the use of my plantation in Patuxent during his lifetime until such time as my grandchild Samuel PRESTON comes of age. In the meantime my daughter-in-law Margaret PRESTON is to be provided for if she decides to give him maintenance. My said son James, on the same conditions, is to have my patent for 200 acres called the Neglect and the island upon the Eastern Shore called Barren Island. My land in Great Choptank called Herne lately purchased of Walter SMITH as per patent for 600 acres to my two daughters Rebeckah and Sarah PRESTON during [t]heir lifetimes, then to my son James, but if all should die, then to my kinsmen and John DASSAY. I have a convenant with William TICK, a Dutchman living in Little Choptank, relating to the delivery of cattle by us in partnership and, when this convenant expires, the said Raphe DASSAY is to have all my cattle remaining. My friend and o'seer Edward NORMAN is to be paid his full wages and at the end of his service 585 lbs of tobasso. Thomas BROCKSON is to be paid his full wages and given 1,200 lbs of tobacco and a cow. William PURNELL is to be given a cow, etc. and to be made free on 20 Oct. next. The said John DASSAY is to have goods to the value of £20 from my house or from the goods being sent from England this year. I leave £20 to George HARRIS to be paid in goods if he comes from England this year and half of the debts due to me in tobacco according to the promise I made him when he went with my son James to England. To my grandchildren William and James BERRY 5,000 lbs of tobacco and to my grandchild Rebeckah BERRY some plate which is to come from England. To my kinsman James DASSAY 4,000 lbs of tobacco. To my said son James half the money I have sent for by James CONEWAY. To Thomas PRESTON upon the Clifts I give the tobacco he owes me. To Isaac HUNT I give goods to the value of £5. To William HARPER I give what is due to him by my Bill. The residue of my estate to my said three children. Execs: My friends William BERRY, Peter SHARPE, John TAYLOR of Kent and John MEERES upon the Clifts. Wits: Enoch COOMBES, George DENLINE, Thomas PEALE and William JONES. AWW 20 Aug. 1670 to the son James PRESTON during the absence of the named execs. (Prob 11/333/101). Richard PRESTON was a leading Quaker