THE FOLLOWING INFORMATION IS THANKS TO Kaye Powell. [contact link]
WITHOUT HER RESEARCH I COULD NOT HAVE MADE THIS CONNECTION. THE QUOTES AND RESEARCH ARE ENTIRELY HERS, NOT MINE.

1. John (of Dorchester) HILL
Birth: abt 1602 in Chard, Somersetshire, England
Death: 31 Ma 1664 in Dorchester, Suffolk Co, MA
SOURCE: See [external link]
Marriage: Frances (TILESTON)TILDEN b: abt 1608 in Chard, Somerset, England

2. Samuel HILL
Birth: 1638 in Dorchester, Suffolk Co, MA Bay Colony
Death: 12 Jan 1708 in Dorchester Vlg, Suffolk Co, MA Bay Colony
Marriage: Martha HANSFORD b: abt 1646 in Dorchester, Suffolk, MA Colony
Married: 1667 in Dorchester Vlg, MA Bay Colony

3. John 1 HILL
Birth: 20 Dec 1669 in Dorchester, Suffolk Co, MA
Marriage 1 Mary UNKNOWN b: abt 1673 in Westerly, Washington Co, RI

4. John 2 HILL
Birth: 3 Oct 1699 in Westerly, Washington Co, RI
Death: aft 1768 in probably Dutchess or Orange Co, NY
Emigrated from Westerly RI via Stonington CT to Beekman Patent, Dutchess Co, NY

Children's names, birthdates and places from:
Settlers of the Beekman Patent
Dutchess County, New York
Volume VI
by Frank J. Doherty

1800 U.S. Federal Census > New York > Dutchess > Phillips
Roll: M32_21 Image: 78 Page: 77
Samuel DENNY
Jonathan HILL 11.2.|..1..|..
William HANNING
Benjamin HILL 11.2.|3.11.|..
Charles HILL 4111.|1..1.|..
Minfur? GILLET
(down, same page)
Patrick FANNING?
David HILL 3..1.|2.1..|..
John ODELL
Marriage 1 Mercy UNKNOWN

5. John 3 HILL
Birth: 21 Nov 1734 in Westerly, Washington Co, RI
Death: 1796 or aft 1800 in Ulster Co, NY - probably Wallkill
Emigrated with father from Westerly RI via Stonington CT to Beekman Patent, Dutchess Co, NY. Siblings' names: Jonathan, David, Caleb, Mercy, Ebenezer, Tacy, Henry, George, Steven.

Appears at Dutchess County NY abt 1752. Eldest child born at Dutchess Co 1754.

A John Hill signed Articles of Association 1775 Beekman, Pawling, Dutchess Co. Business records continue there through 1777, prior move to Wallkill, Ulster County.

1790 U.S. Census New York Ulster Wallkill
John HILL 113.. Abial still at home & 2 daughters?
Tilton HILL 121.. p 218 also
Caleb HILL 142..
Tilton EASTMAN @ Wallkill, Ulster *enumerated between Caleb & John p218
Abial FRY @ Minisink, Orange
Matthew SMITH p 216, R, Wallkill

1800 United States Federal Census > New York > Orange > Wallkill
Roll: M32_21 Image: 342 Page: 339
HILL Caleb 212-1|21-1--- 45 or older, same page as jr
HILL John Jr 2--1-|211---- age 41=und 45
(and)
Roll: M32_21 Image: 344 Page: 341
HILL John --1-1|-11-1-- 45+, adult m not Abiel, 2 dtrs? *died 1796?
HILL Tilton 42-1-|2--1--- (2nd listing down)
* I suspect John enumerated in error as living, as it was his home & family? Or is this John b 1759?

1800 U.S. Census New York Tioga Owego
up to 10, 16, 26, 45, 45+
Jonathan THOMAS 1.1 ..|..1.. anc p 1/10
John HILL 1.. 1.|2.1.. age 27-45
Thomas HILL ..2 .1|....1 ??
John HILL 34. ?1|12..1 age 45+
Joseph THOMAS 12. .1|2111.
*Caleb, Tilton, Abiel HILL @ Orange Co.
Abiel Fry @ Tioga Co
Tilton EASTMAN not indexed, may have died

1810 U.S. Census New York Orange Wallkill p 461
John HILL 2--1-|1--1- couple 26-45, 2 sons, 1 dtr
Tilton 1810 U.S. Census New York Orange Wallkill p 486
Caleb 1810 U.S. Census New York Orange Deer Park p 453
Abial F HILL 1810 U.S. Census New York Orange Deer Park p 453
John Hill 1810 Minisink, Orange, NY --1-- single man und 26

John Hill 1810 Montgomery, Orange, NY ---1-|112-- 26-45, no sons. Likely descendant of Caleb of Dover, brought William (black) Hill.
Marriage 1 Polly EASTMAN b: 1735 in New Fairfield, CT
Father: Peter EASTMAN b: 16 Jun 1712 in Suffield, Hartford Co, MA (later CT)
Mother: UNKNOWN LAIRD LORD b: abt 1712 in probably CT
Married: abt 1752 in Dutchess Co, NY
NOTE: 1st John & Polly's other children were Caleb, Marcy, Mary, Tilton Eastman, Johanna, Sarah, and Abial Frye HILL.

6. John 4 HILL
Birth: 18 Mar 1759 in Kingston, Ulster Co, NY
Death: 25 Aug 1849 in Cayuta TWP., Chemung (now Schuyler) Co, NY
John's elder brother Caleb served in the Revolution. Born 1759, there is good enough reason to think John may have also. I do not know what document it is but one found at HeritageQuest with # S43683, 1 of 5 -- no data, just name John Hill, service: New York.

Family moved first from Dutchess Co to Ulster, apparently later from Kingston to Wallkill, Ulster Co, NY ~1765-9 (later Wallkill Town(ship) Orange Co. Not the same as Ulster Co's village of Wallkill; County line changes. Kingston may have been Church town thus church records, rather than residence.

1790 > New York > ULSTER > WALKILL TWP
Series: M637 Roll: 6 Page: 218
John HILL 113|..
Tilton HILL 121|..
Caleb HILL 142|..
(all same page, right side) John Sr has self? 16+, 1 male under 16, 3 total females. No idea where John Jr is that census, not with brothers. Doesn't seem like he'd be the one at New Paltz unless moved in with inlaws? possibly:

1790 > New York > DUTCHESS > CLINTON
Series: M637 Roll: 6 Page: 101
John HILL 1-2--

1790 United States Federal Census > New York > Ulster > New Paltz
Roll: M637_6 Image: 0503 Page: 179
John HILL 116-- could be. self age 30, son 3rd, wf, up to 5 dtrs.

1800 > New York > ORANGE > WALLKILL
Series: M32 Roll: 21 Page: 339
John HILL Jr 2..1.|211....
(near brother Caleb) John age over 45 + two boys and two girls under 10 and one girl between the ages of 16 and 25; woman over 26 under 45. John Sr lives near Tilton, also at Wallkill. There should be a 3rd daughter but John's 1849 will names only 2 - one deceased(?) or a female not-daughter.

Son Joseph states born Tioga Co NY 1807:
1810 United States Federal Census > New York > Tioga > Spencer
Roll: M252_37 Image: 95 Page: 654
HILL John 21-1-|2111-|--

1820 U.S. Census New York Tioga Spencer
John HILL 21-2-1|111-1-|3--
Abner FLANDERS 1---1-|1-1---|---
John SHOEMAKER -1--1-|11-1--|1--
(John is over 45, Sallie 26-45, making Sallie's birth year 1776-1794)

1830 U.S. Census New York Tioga Cayuta
Roll: M19_109 Image: 322 Page: 155
HILL Sacket 21-1---------|----1-------- Sacket's age bracket wrong*
HILL John ---1---1-----|---11-1------ m 50-60*, f 40-50
HILL Joseph 1---1--------|----1--------
HILL Hugh 211--1-------|1---1--------
WESTBROOK Peter 2---11-------|-1--1-------- sister Fanny/Anna
*I believe John to be nearer 70. I know Sacket is 30, not "15-20".

Family lore states wife #1 was Sarah COLYER, spelled out precisely and pronounced coal-yr, said a Dutch name, per grandmother Violet Mae HILL about 1948-9. Same 1940s informant also gave the next generation back (and more), and that John moved to what would be Chemung from around Goshen, Sullivan County. Violet also stated that Sarah Sally THOMAS, by name, raised Sacket. The only likely error there may be that it was the McKinney-Cook side who migrated from Goshen - which could be my own mistaken recall who did which.

Corroboration - John Hill Jr m. Sarah Colyer 1782.

per Elaine Sunde:
"In NY Marriages Previous to 1784 (Albany: Weed Parsons & Co, 1860) Sarah Colyer and John Hill Jr. are listed as being married August 5, 1782, having posted a marriage bond. The volume indicates that marriage licenses were issued from the Provincial Secretary's office in exchange for Penal sum of 1,500 that "no lawful let
Marriage 1 Sarah COLYER b: abt 1763 in NY
Married: 5 Aug 1782 in likely Albany, NY

7. Deborah HILL
Birth: 1794 in NY
Death: 1850 or aft in Gallatin Co, IL
Marriage 1 Abner FLANDERS b: 22 May 1790 in Concord NH
Married: 1820 or bef in Tioga Co, NY
~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
HILL FAMILY SOURCE NOTES:

NOTES ON DEBORAH HILL:
PER ROOTSWEB MESSAGE FROM K. POWELL:
that Deb's brother Morris Hill's (this is getting tricky) son Benjamin O Hill's widow Eliza Newman remarried Willis B Hargrave, son of Seth (I'm told; unverified for myself). This second set of children for Eliza includes a William Willis Hargrave. The 2 married 1878 and combined familes and made more ...AND..... Deborah's brothers (or half-brothers) Joseph and Morris (and maybe Abner too) HILL settled at Carmi late 1820s. Morris' son Benjamin O. HILL married Eliza NEWMAN. The HILL sibling's father was John of Tioga (later Chemung) Co, NY. Her brothers (half-brothers?) Morris married Caroline PERRYMAN 1837 Carmi, White Co, IL. Next came brother Joseph and NY-born wife Mary Ann WEAVER with 3 children - their first IL-born was Fanny b. 1842 Carmi, White Co, IL.
It appears that 2nd John's children were Anna (Fanny?), Hugh, Deborah, and Sacket HILL (my ancestor) by Sarah COLYER who remained in NY. Next wife is Sallie (Sarah?) THOMAS and sons Joseph, Abner, and Morris. No children are known with 3rd wife Elizabeth UNKN.
HILL offspring remaining at Chemung Co NY were Hugh who married Calista/Celesta ELLIS, Sacket who married Elizabeth SHOEMAKER/SCHOONMAKER, and Anna. Anna *may likely be* Fanny, who married Peter WESTBROOK.