On October 31, 1765 the Hillsborough Township land was granted to Robert Cummings and four others.92 Robert's portion was 23,750 acres and he was land agent for the settlement.
He was a nephew of Adam Hoops whose group had received the nearby Germantown (Shepody/Hopewell) land grant on Sept. 24, 1765.92,91
The spelling Cummins appears more often on original documents, including his letters and his mother’s will. His name is spelt Cummings on his uncle Adam Hoops’ will but that document mispells many names including two of Hoops’ son-in-laws. In Nova Scotia, his daughter’s name seems to be accepted as Cummings.
Either he was a bigamist or he had an extramarital relationship with Rosanna. There is no indication they ever lived together as a family. In 1770 he left his Hillsborough grant under the management of Charles Baker in order to go manage his uncle’s Germantown settlement on the Shepody River, replacing Thomas Calhoun.92
In 1771, William Calhoun visited Germantown and wrote in his diary of an encounter with Cummings: “Friday the 26th [of July] I went with my brother to Germantown, where I was kindly received to the country by Mr. Cummins. I returned home that evening. ... I concluded to stay some time in the country ... Sunday the 27th of July being a clear, pleasant day, ... I set out with Mr. Cummins, Mr. Eagleson and my brother to see the land and settlements in the Petitcodiac River, at the estuary of which I sat filled with amazement at the beauty of the river and the surrounding country. We landed at Moses [De]Lesdernier’s Esq., Proprietary agent for the Township of Hillsboro’. From him I learned the terms of settling the aforesaid township, and as I liked the terms of the settlement very well ... I took a walk with my brother through the woodland and lots adjacent to it, and both being well pleased with the appearances of the land, we agreed to make application for five lots each. Each of these lots contained, facing the river, fifty acres of upland and ten acres of marsh. Continuing our walk we crossed over some land which was of excellent quality, and went to some neighboring farms, where they told us that everything put into the ground seemed to flourish.”92
In 1772, Cummings left Rosanna and his child and returned to Maryland where he had an estate 12 miles from Baltimore named “Monckton Mills”.
From “The First Hundred” by E.W. Larracey:
“There are indications that in far-off Baltimore, Robert Cummings already had a wife and that he concealed his dual-marital status both from a person he referred to as ‘Madame’ and also from Rosanna...
on the night of July 19, 1773, Cummings...was penning a letter to Charles Baker, who had taken over the supervision of the Hoops grant in Hillsborough. In a finely executed hand, he wrote:
‘I am sending you £40 worth of things ‘your money’ so that Rosanna may be able, with the assistance of her friends to barter these goods for furs with which she may be able to purchase a handsome stock of cattle. In the meantime I shall be glad to hear from you respecting her conduct and the care she has taken of the child, but in a mistical (sic) manner that it may not be understood by everyone lest it might fall into the hands of some other person, particularly Madame, whom I expect in a few months: This is a secret to be kept to yourself.’”91
From the same letter: “...I expected to have had the pleasure of seeing you at Hillsborough before this time but my friends were much bent against my return to Nova Scotia to settle since which I have purchased a Small Estate in Maryland within Twenty Miles from Baltimore...I have still a liking to Nova Scotia and hope to see you at Hillsborough next spring when I shall come and make out and give those people who are setled [sic] on my Land their Deeds...” In fact he never returned to the settlement, and in 1775 the American War of Independence precluded further contact.92

The Archives of Maryland online have record of Robert Cummins of Monckton Mills being a “supplier of victuals” to troops during the American Revolution in 1776 for which he was paid 1500 pounds on Apr 24, 1777 by the Western Shore Treasurer by order of the Maryland Council of Safety.109

Robert Cummings served as Captain in the Baltimore County Militia during the American Revolution.110
Transcribed by Craig O'Donnell from ARCHIVES OF MARYLAND series vol 16:
“Sat 30 Aug 1777...
Commissions issued to...
Robert Cummins Capt, Abraham Hicks first Lieut, John Miller second Lieut., Samuel Tipton Ensign, Stophel Shroad first Lieutenant, Matthias Backley second Lieut & Henry Peckly Ensign of Capt John Showers's Compy and Charles Allen Ensign of Capt Robt Lemmon's Compy belonging to the Upper Batt. of Militia in Baltimore County.”110

From Rainer Hempel:
“He left a Will in the hands of Rev. Eagleson in 1772, to be opened only in the event of an accident...Petition by Rev. John Eagleson and Charles Baker on behalf of Elizabeth Cummings for land from Robert Cummings’ former grant in Hillsborough; PANB, New Brunswick Land Grants, Microfilm F 6648”
“In his will, Cummings states that his ‘natural son, Benjamin’ should receive one-quarter of his Hillsborough share, and that an equal portion go to Elizabeth, his ‘natural daughter, by Rosanna Treits [sic].’ It is clear from the context of the Will that Benjamin was the issue of his relationship with ‘Madam’ of Baltimore as he makes special mention that only the existence of Elizabeth be kept secret; petition on behalf of Rosanna Treitz and Elizabeth Cummings, PANB, Land Petitions, Surveyor General, George Sproule, 1787, Microfilm F 6648.”92