Sorry not to have responded sooner.
In reading Hilton genealogies most people start with William the immigrant as William I...so this is generally the layout:
William Hilton and Ellen Mainwaring 2 kids (of England)
William I (the immigrant)& wife Francis Hayward (I have 5 children)
William I & unknown wife (2nd wife, I think)
William II & Ann Beal (or Beales) (I have 8 children)
William III & Margaret Gould Stilson (10 or 11 children)
Broadbay is the area at the Bremen/Waldoboro town line where the Medomak River opens up into what's known as Broadbay. However, it seems that West Waldoboro and the upper part of Bremen were often (and loosely) called Broadbay. That type of thing happened a lot before towns became incorporated.
So, when you see that location used keep an open mind that its in that general vicinity, but could be somewhat far reaching. You may also see the area called Broad Cove.
I live in North Nobleboro, so I'm not too far from you.
My Hilton line goes:
Tom Moody (Ona Hilton Moody, Henry M. Hilton, Clyde W. Hilton, George W. Hilton, William Bainbridge Hilton, Charles V. Hilton, Joshua Lee Hilton, Capt. James Hilton, William IV, William III, William II, William I). Phew!! (I also am descended from William IV's daughter Anna Hilton McCurda through my paternal grandmother.)
The James Hilton you asked about who was the guardian of Mary Matchloffe was the Capt. James in my above line. She would have been James' niece. Mary Hilton, the daughter (and oldest child) of Wm. IV and Mary (Lee) Hilton married Mathias Matchloffe. Both of these individuals appear to have died young (she may have remarried). Mathias died about 1757 leaving, I believe, only the one child Mary Matchloffe.
I have a website that has some Hilton info on it at: http://www.gencircles.com/users/thomasmoody/1
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