Listed on a list of original proprietors of Taunton that dates to 1638 or 1639. He is found in 1641 in Windsor, receiving an average size grant of 16 acres.

He may have arrived on one of the ships that left Weymouth, England in Apr 1637, as several of those families ended up in Taunton.

Recorded in the 1640 Town Records at Windsor in the list of “First Settlers of Windsor, five years after their removal from Dorchester.” (NEHGR 5:365) [The list includes people who arrived after 1635, such as those who came with Huit in 1639]

On his death, town records of Windsor gave the following account: " August 17, 1659, John Drake, Senior dyed accidentaly, as he was driving a cart loaded with corn, to carry from his house to his son Jacob's the Cattle being two oxen and his mare, in the high way against John Griffin'ssomething scar'd the Cattle, and they set a running, and he labouring to stop them by taking hold on the mare, was thrown down on his face, and cart wheels went over him: brake one of his legs and bruised his body, so that he was taken up dead, being carried into his daughter's house and life come again, but dyed in a short time and was buried on the 18th day of August 1659." [53]

There are pedigrees floating around linking him to the Drakes in Ashe, Devon (the family of the navigator Francis Drake). However, that family was of considerable prominence and wealth, which is not reflected in the social standing of this John. In addition, the wills of the family don’t mention him, with the exception of that of Francis in 1634 (the source of the speculation in the first place). He is also not likely the John Drake who came with Winthrop’s Fleet to Boston in 1630. That John is listed as one to be made a freeman in Oct 1630, but did not actually take the oath. Most of the other men of whom that was the case died or returned to England. Furthermore, there is no other record of John Drake until 1638. It would have been virtually impossible for a man with a family to avoid any mention for 8 years. (See articles in The American Genealogist for a more in depth explanation - excerpted here: http://www.xroyvision.com.au/drake/history/hist33.html.)

Savage’s: JOHN, Dorchester, or Boston, came in the fleet with Winthrop prob. as we find his req. 19 Oct. 1630 to be made freem. yet his adm. is not found, and he rem. from our col. perhaps as a purch. of Taunton 1639 [Baylies, I. 286], and not long after to Windsor, and there, by a cartwheel running over him, was k. 17 Aug. 1659, leav. s. Jacob and Job, bef. ment. and John, beside one, if not more, d. His wid. d. 7 Oct. 1681, but we may hesitate at the old ch. rec. story of her hundredth yr. yet agree to the main truth of her being call. "old wid. D."

First, I bequeah my soule to God that gave it me, and my body to Earthly burial. As for my worldly goods, I thus dispose of them: First, I desire that there may be a Inventory tooke off my State and within twelve months after my decease: I give to my son John L20; and after my wyve's decease, out of the State I have, I give him tenn pounds more; and to son Job I give my six acres of meaddow that is bounded of the South side with Goodman Phillps, Within twelve moneths after my decease, then, after my wife's decease, I give that six acres forementioned to his sonne Job; and after my wife's decease, I give to all grand children, viz., three of sonne John, and four of my sonne Job, and one of my daughter Elizabeth Gaylord, three pounds apeece; and too my wife I give all my part off Howsing and Lands that Ihave in possession ffor to make use of as shee and her ffriends shall think will be fore her best advantage; and my land that I bought of Goodman Bissell that Lye of the East Side of the great river I give to my sonne Jacob provided that he pay to my sonne John tenne pounds after my wif's decease, ffor to make his porshon L30; the house and my land that I bought that was Mr Sen Nicholases (Mr. John Saint Nicholas) that lys of the west side of the great river I give to my sonne Jacob, and after my wife's decease he shall pay the rest of his brothers & sisters sixteen pounds ffor the Land that I have given to my sonne Jacob; my wife is to have the propriety of it for her use while shee live, and after her decease then my sonne Jacob shall have full possession of it with its appurtenances yt appertain thereunto, provided that he pay the formentioned Sums of money to his Brethren, viz., tenne pounds to my sonne John and sixteene pounds to the rest of his brothers and sisters; too my sonne Jacob I also give him my two tables and a bedsted that he maks use of yt belongs to that end of the House next the Highway in the lower romms; to my daughter Mary Gayler I give one fetherbed and two blankets and a bolster after my wife's decease; and to my daughter Elizabeth I give one coverlid after my decease; and to Timothy I give him forty shillings and two good sutes of clothes when his time is out; and the rest of Stock shall be equally divided amongst my five children after my wife's decease."

Likely connected as a cousin of some sort to the famous William, who was born in Warwick in 1564 and whose mother’s name was Mary Arden. WC connects as daughter of Henry, William’s uncle, but if source is IGI, that record says she died in1595.