Childen:

Hugh Humphrey (8 Dec 1749 - 25 Oct 1840) m. 1776, Mary Desire Pixley
Robert Humphrey (1751 - 30 Nov 1840)
    c1. George C. Humphrey (abt 1787 - )
David Humphrey (~1763-1846)

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Robert Humphrey

In his Rev War Pension Application he stated he was born in 1751

Census (US Federal) Minisink, Orange, New York 1790
Census (US Federal) New Windsor, Orange, New York 1800
Census (US Federal) New Windsor, Orange, New York 1810
Census (US Federal) New Windsor, Orange, New York 1820
Census (US Federal) New Windsor, Orange, New York 1830
Deposition New Windsor, Orange, New York Sep 10, 1832 (80y)
Census (US Federal) New Windsor, Orange, New York 1840 84y
    he died in this same year and probably remembered his age wrong
    living with his son George C. Humphrey

George C. Humphrey
Deposition Orange, New York Nov 30, 1840 57y

According to History of Great Barrington, (Berkshire County,) Massachusetts, p 255, there was a Robert Humphrey (age 28, 5 feet 10 inches, complextion light) mustered into the regiment of Col. Benjamin Simonds on June 28, 1779. The entry says he is from Muddy Brook which is where David and Hugh Humphrey relocated to in 1772 (pg 220).

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David Humphrey

He stated that he was 13 years old in 1776 when his brother, Robert, enlisted
He was not named as a Revolutionary War Soldier in the 1840 census
He gave a deposition for his brother, Robert's, Rev War pension application in 1833 when he was 71 years old

Census (US Federal) Claverack, Columbia, New York 1800
Census (US Federal) Claverack, Columbia, New York 1810
Census (US Federal) Claverack, Columbia, New York 1820 includes 2 males over 45 years
Census (US Federal) Claverack, Columbia, New York 1830
Deposition Claverack, Columbia, New York Apr 9, 1833 71y
Census (US Federal) Hudson, Columbia, New York 1840

Yesterday I started to analyze a letter that Great Barrington militia colonel and politician Mark Hopkins wrote to the Massachusetts Council in March 1776. The town had formed two militia companies and elected militia officers, but a lot of the rank and file were coming to him with complaints about those officers.

Hopkins, little brother of the town's Congregationalist minister, explained what he saw as the root of the problem:

It must be observed that the town consists of members of the Church of England and Dissenters [i.e., Congregationalists]; the former of which (a few excepted) have been very backward in all our late publick matters, and amongst us are denominated Tories. It is said that by their interest principally, the aforementioned officers were elected. They have never turned any men out for the publick service, which the other party have; and thus, being all present, are able to outvote the Whigs.

I was surprised to read about an Anglican church this far into the New England countryside. Most were in seaside communities where significant numbers of merchants and mariners had arrived after the early-1600s Puritan migration. In contrast, Great Barrington is in Massachusetts's westernmost county.

It looks like geography was a big factor behind this Anglican outpost in the Berkshires as well: it was so far west that it was close to northern New York, and there was an overlap between Massachusetts's claims and a patent issued by New York in 1705. The Great Barrington settlement therefore included a community of Dutch descent who had come east from Albany.

Those Dutch families preferred to worship more in the style of the Lutheran churches they had grown up with. The town's adherents to the Church of England thus included men named Burghardt, Schermerhorn, and Van Deusen. The new church also gained support from some of the local gentry, such as David Ingersoll, Jr., a young lawyer from Yale like Hopkins.

Great Barrington's Anglicans organized themselves into a parish in 1762 under the guidance of a minister from Connecticut. They started to build a church two years later. Gideon Bostwick, yet another Yale graduate, read the prayers before going to England to receive holy orders and coming back as the church's Anglican minister in 1770. Five years later, Bostwick and his wardens could list fifty men who usually attended their services, and that was evidently a significant voting bloc in the town militia.

Having described the militia split, Hopkins discussed a possible solution based on what later generations called gerrymandering, but also said most locals weren't ready to take that step:

A petition has been presented to me, signed by fifty-four persons, requesting an alteration in the division of said companies into East and West Companies [instead of north and south]. By the proposed new division, the main of those called Tories will be in the West Company. The petitioners imagine that, upon a choice according to this division, such officers would be chosen as would give general satisfaction. The other party say that this proposed division will give as great uneasiness as the present, and they, to the number of eighty-seven, have petitioned against the proposed new division.

The Field-Officers, upon the present appearance, are of opinion that, if the now proposed division had been made at first, it might have been for the best; but after we had proceeded to make a division, and a choice of officers has been made accordingly, thought ourselves hardly warranted to make a new division without the direction of the honourable Council; and the rest of the Field-Officers directed me to write to your Honours upon the matter. William Whiting, Esq., the Representative from the town, can fully inform your Honours of the difficulties and circumstances attending the whole matter, to whom we refer for that purpose.

I beg leave further to mention, that a part of this town, called the Hoplands, containing about thirty-eight men, is separated from the rest of this town by mountains, in such a manner that the people there cannot get to the place of parade here without travelling eight or ten miles. They lie contiguous to a part of Tyringham; we therefore determined that they should join that part of Tyringham, and so make a company; but upon notice, the said Hoplanders refused to join with Tyringham. They are so few that, by the act, they cannot be formed into a company by themselves; so that, as matters now stand, they must be obliged to join the North Company in this town; and yet they have had no voice in the choice of the officers, it not being known but that they would be willing to join with Tyringham till after the choice here.

We look to your Honours for direction in these matters, not doubting but the people will acquiesce in what your Honours shall direct in the premises.

I suspect this was the sort of problem that the legislature liked locals to work out for themselves, especially when they were on the far side of the province. But Hopkins wanted the authority of the General Court to act.

https://archive.org/details/historyofgreatba00tayl
History of Great Barrington, (Berkshire County,) Massachusetts
by Taylor, Charles J. (Charles James), 1824-1904
Published 1882

Page 220:
As early as 1772, James and William Ray from Rhode Island, Henry McGonegal from Volutown, Conn., David and Hugh Humphrey, and Martin Remele had located in Muddy Brook.

Page 240:
The first recorded election of the committee of Correspondence Inspection and saftey was on the 18 th of March 1776 ... The office was an important one, and the powers delegated to or assumed by this committee were as extended as the exigencies of the times demanded. It cometimes - in the absence of the courts which had been supressed and not yet organized - usurped the powers of the judicial tribunal, in which it was sustained by the people. The committee in other years was composed as follows:
1777, David Humphrey ...