Thank you! I finally found the connections on Family Search with enough reliable sources listed that I think I have connected Sir Winston Churchill to the Gifford family of Westport, MA, correctly.
I was tipped off by this connection by chance. One of my Facebook Groups is the Historical Society of Westport which I joined when I discovered that most of the original founders of what was then part of Dartmouth, MA, settled there in order to establish a Friends Meeting in an area that was safe for them to worship as they chose.
The Historical Society is thoughtful enough to post videos of some of their winter programs which is helpful to me because I live in Upstate New York (the Adirondacks) and can't attend their meetings. Richard Gifford, a descendant of many of the early settlers recently presented a program about the Gifford family and mentioned that Churchill's 3x great grandmother was Meribah Gifford. Naturally, curiousity got the better of me and now I can say that the connection is complete!
If there are any Gifford descendants on WikiTree, I can provide the url for the program.