The book "Churchill Family in America" (Gardner Aseph & Nathaniel Wiley Churchill, 1904) did not indicate from where John Churchill emigrated to Plymouth Colony in the 1640's. It's supplement in 1968 also posed the unanswered question about the relationship of John's line to that of Winston Churchill.
The Ancestry File of the LDS may be able to answer the former question and offer some insight into the latter. According to the LDS, John Churchill and his ancestors back to his great grandfather William Churchill came from Dorset county on the south coast of England. Muston, a now non-existant town in Dorset, seems to have been the ancestral home of Churchills, according to Burke's Family Index. Based on historical maps, Muston may have been located near the present day town of Winterbourne Kingston.
Regarding any relationship of John's line and that of Winston Churchill, the LDS offers intriguing clues. Winston's ancestor and namesake Sir Winston, father of the famous Duke of Marlborough (also John), was born at Muston in Dorset in 1620. He and the 20th century Winston had an ancestor named William in the 1530's in Muston. As you'll see below, our John of Plymouth also had an ancestor named William in 1530's Dorset. The former William was married to a Mary Cruwys while the latter William was married to a Mary Cruese or Crense. Could Cruwys and Cruese be the same name spelled differently?
Interestingly, there is evidence that the Churchills of Northern Maine are related to Sir Winston via his mother, the American Jennie Jerome. See the link to Northern Maine for more on this intriguing irony.
 | Northern Maine |
Here is the Dorset line to John Churchill of 1643 Plymouth Colony:
| William Churchill (b 1531 Dorset, England) = Mary Crense or Cruese (b 1535) |
| John Churchill (b 1561 d 31 May 1621 Muston, Dorset, Eng.) = Eleanor Meller (b 1565 Muston, Dorset, Eng) |
| John Churchill (b 1603 d 23 May 1682 Steeple, Dorset, Eng) = Sarah ?? (b 1602 d 23 Oct 1678 Steeple, Dorset, Eng) |
| John Churchill (b abt 1620 d 1 Jan 1662/3 Plymouth, Plymouth, Ma.) = Hannah Pontus (b 1623 d 22 Dec 1690 Plymouth, Plymouth, Ma.)....This is the John Churchill who first appeared in the records of Plymouth Colony in 1643. |
Why did John emigrate to Plymouth Colony. We may never know, but here are some interesting facts. Between the Mayflower's landing at Plymouth in 1620 and the early 1640's, approximately 25,000 English subjects immigrated to New England. The English Civil War was heating up in the early 1640's, maybe John wanted to get away from that. Interestingly, Sir Winston (mentioned above) was on the royalist side, the losers to Cromwell's roundheads, and lost most of his property. If John was related to his contemporary Winston, maybe he too was on the wrong side and chose New England over remaining in the Lord Protector's England. So, John may have emigrated for any of a number of reasons, political, religious or economic.