Following is a report I received from J. Kelsey Jones, a descendant of Obadiah CROSBY. I have not verified this information.
It is believed that most of the Crosbys of Putnam County, New York are descended from Thomas, David, Joshua, and Isaac Crosby who removed there in the mid eighteenth century from Harwich, Barnstable County, Massachusetts. They settled on a section of the Philipse Patent, which comprised nearly the present county of Putnam (then Dutchess) County, granted in 1697 to AdolphPhilipse. Of the four Crosbys, Joshua and David were brothers and cousins to Thomas and Isaac, the latter two also being cousins to each other. Isaac Crosby was a descendant of William Brewster of the Mayflower through hismother, Patience Freeman and the other three Crosbys all married descendants of Stephen Hopkins of the Mayflower.
The problem evolves of determining which of the four Crosbys the various Crosbys in Putnam County are descended from. Thomas Crosby and his wife had eight children born at Harwich, Massachusetts, the last in 1752, and one could assume more children were born after their removal to Dutchess (that portion that is now Putnam) County. Elizabeth was forty years of age at the birth of her eighth child in 1752. David Crosby and wife had four children born at Harwich and four more children born after their removal to Dutchess County. Eight children were named in the Will of David Crosby. Joshua Crosby and wife had six children born at Harwich and other children born after their removal to Dutchess County. Joshua Crosby left a Will in which he named eight children. The last of the four Crosbys of our concern is Isaac, who it is said was the first Crosby to remove to Dutchess County, New York. No children are recorded at Harwich for Isaac, which may indicate that he did remove to New York state at an early date. He left no Will and his complete family is unknown. Since the children of Thomas, David, and Joshua Crosby are known, one would assume the other unplaced Crosbys would be children of Isaac Crosby, but proof of making such an assumption is lacking. There were no vital records kept in Dutchess County as there had been in Harwich, Massachusetts and thus many dates are lacking after the families removed to Dutchess County. The records of the church at Philippi (now Southeast) begin in September 1786. The first book of records of this church were lost, which would have contained important information on the Crosby families. In the American Revolution, twenty one Crosbys were members of the Dutchess County militia. Abner, David, Eli, Encoh, John, Joshua, Josiah, Moses, Nathan, Reuben, Samuel, Thody (Theodorus), and Thomas were sons of Thomas, David, and Joshua Crosby, while Peter and and James were grandsons. Of the six remaining Crosbys, Solomon and Eleazar were sons of Isaac, leaving Joseph, Obadiah, Lemuel and Issac who were also perhaps sons of Isaac. The Crosbys settled in what is now the present towns of Carmel, Northeast, Patterson, and Southeast in Putnam County, New York. Putnam County was formed from Dutchess County 12 June 1812. Thus, the early records from the mid 1700's to 1812 for the Crosbys refer to Dutchess County, though their residence was in what is now Putnam County. The Crosbys settled on what was known as "The Oblong," an area in eastern Putnam County, being a strip of land one mile, three quarters, and twenty rods wide. A portion of this was formed as Frederickstown and still later, Southeast. Much of present Southeast embraces lot 9 of the Phillipse Patent and the south half of lot 8. Southeast is bordered on the west by Carmel, on the north by Patterson, on the east by the state of Connecticut, and on the south by WestchesterCounty. Most of the farms in the area were held by lease until 1811 when the Philipse family began to sell the farms. Thus, there are no deeds for much of this area in the 1700's, because of the perpetual leases given to the tenants by the Philipse family.
1. Thomas Crosby b. c. 1705 bpt 19 Aug 1705 Harwich, Massachusetts son of Thomas and Hannah Crosby, m. 9 Aug 1733 at Harwich, Elizabeth Hopkins b. 21Apr 1711 Harwich daughter of Nathaniel Hopkins and Mercy Mayo and a fifth generation descendant of Stephen Hopkins of the Mayflower. Thomas and his family resided at Harwich and the births of eight children were recordedthere. Thomas appears on the tax list in Fredericks Precinct, Dutchess County in 1747, but evidently had not removed his family there by that date, since it is related that his son, Enoch Crosby was three years old when they moved to New York state, which would place the date at 1753. Futhermore, youngest son, Thomas who was born in 1752 is recorded in Harwich vital records. Thomas was dismissed 1 Aug 1756 from the First Parish Church ofHarwich "to ye church in or near ye Oblong, under ye care of ye Rev. Kniblow." He and his family are related to have settled in what is now the present town of Carmel, Putnam County and occupied a farm, which included the old Gilead burying ground. He was living there in 1754 and 12 Apr 1762 on a survey of lot no. 6 (now Carmel). In 1766 the farm was leased by Philip Philipse to James Dickison "formerly in possession of Thomas Crosby." He is related to have removed to the eastern portion of the town of Southeast, which town borders Carmel on the east. However, if they resided in the town of Southeast, they then removed to the town of Northeast as he was assessed at Northeast, Dutchess County from 1771-9 and listed in a return of inhabitants of Northeast Precinct, Dutchess County, 5 July 1775 who signed the Revolutionary pledge of Assocatioan [sic]. Thomas d. 13 Dec 1781 77y (ts)buried Mountain Cemetery, North East (Patterson), Putnam County, New York. Elizabeth d. 6 Aug 1801 92y (ts) buried Gilead Burying Ground, Carmel.
5. Bethiah Crosby b. 22 Mar 1734 bpt 15 Apr 1739 Harwich, Massachusetts d.12 June 1752.
6. Phoebe Crosby b. 28 June 1736 bpt 15 Apr 1739 Harwich.
7. Hannah Crosby b. 14 July 1739 bpt 22 July 1739 Harwich.
8. Elizabeth Crosby b. 12 Jan 1741/2 bpt 24 Jan 1741/2 Harwich.
9. Benjamin Crosby b. 9 Aug 1744 bpt 19 Aug 1744 Harwich.
10. Jeremiah Crosby b. 11 Feb 1746/7 bpt 15 Feb 1746/7 Harwich.
11. Enoch Crosby b. 25 Dec 1749 (Harwich vr) 4 Jan 1750 (his own record) bpt 31 Dec 1749 Harwich.
12. Thomas Crosby Jr., b. 3 Feb 1752 bpt 3 Feb 1752 Harwich.
2. David Crosby b. 13 Apr 1709 bpt 22 May 1709 First Parish Church, Harwich, Massachusetts son of John and Hannah Crosby, m. 19 June 1735 at Harwich, Reliance Hopkins b. 17 Nov 1709 Harwich bpt 24 July 1715 daughter of Samuel Hopkins and Lydia Rich and a fifth generation descendant of Stephen Hopkins of the Mayflower. Her sister, Lydia m. David's brother, Joshua. Reliance was admitted to the Harwich First Parish Church, 15 May 1737 and David was "admitted to full communion, eodem tempore, 1742." Their older children were baptised in this church, the last baptised 13 Jan 1745 after which date they removed to the Oblong on the Philipse (sometimes Phillippi) Patent in Dutchess (that portion that is now Putnam) County, New York. David appears on the 1747 tax list of Fredericks Precinct. He and his wife and other relatives were dismissed from Harwich First Parish Church to "the church in the Oblong 3 Sept 1749, under ye pastoral care of ye Rev. Mr. Kent." The Will of Samuel Hopkins dated 6 June 1749 named his daughter "Reliance Crosbee." David was residing on lot no. 8 (present Southeast, Putnam County) in 1754 and 1 May 1768. On 1777 tax list of Fredericks Precinct. David and Reliance were members of the church at East Phillipi (Southeast). His Will dated 29 Aug 1782 Fredericks Precinct, names wife (unnamed), daughters, Susannah Garrison, Reliance Crosby, Sarah Towns, and Hulda Youngs, sons, David, Abner, Eli, and Moses. David and Abner were executors. Witnessed by David Crosby Jr., Abner Crosby, and William MacClure. Signatures acknowledged 14 May and proved 8 Aug 1794. The markers of David and Reliance stand in the Sears Burying Ground at Doanesburg in the town of Southeast, Putnam County, New York. "In memory of David Crosby the Elder who departed this life Oct 20th 1793 in the 85th year of his age. In memory of Mrs. Reliance Crosbey wife of Mr. David Crosbey who departed this life Feb 25th 1788 in the 75th year of her age."
13. David Crosby Jr., b. 6 Sept 1737 bpt 18 Sept 1737 Harwich,Massachusetts.
14. Susannah Crosby b. 19 Aug 1740 bpt 1 Sept 1740 Harwich.
15. Reliance Crosby b. 14 Nov 1742 bpt 16 Jan 1743 Harwich is called"Reliance Crosby" in the Will of her father dated 29 Aug 1782 and her sisters were called by their married names. She would have been thirty nineyears of age at that date. It was perhaps her niece, Reliance b. 1769 daughter of Abner Crosby who m. Jeremiah Burgess, since two sons were baptised in 1790, to late to be children of Reliance b. in 1742. There were two Reliance Crosbys who were members of the Phillippi Church, 7 Sept 1786, evidently her and her mother, since her niece b. in 1769 would have still been a minor. Jeremiah Burgis and Reliance, his wife, were added to the church rolls 6 Dec 1789. In the Sears Burying Ground is "Naomi daughter of Capt. Jeremiah Burgis d. 1Mar 1789 22y. If Naomi's mother was Reliance, she cannot be the Reliance b.in 1769, but the marker gives no name for the mother of Naomi.
16. Abner Crosby b. 25 Dec 1744 bpt 13 Jan 1745 Harwich.
17. Sarah Crosby b. 1747 bpt 17 May 1747 Harwich.
18. Eli Crosby b. 1749 Fredericks Precinct (that portion that is now the town of Southeast, Putnam County, New York).
19. Moses Crosby b. 1755 Fredericks Precinct.
20. Huldah Crosby b. 1758 Fredericks Precinct.
3. Joshua Crosby b. 4 Aug 1712 bpt 7 Sept 1712 Harwich, Massachusetts son of John and Hannah Crosby, m. 2 Aug 1733 in Harwich, Lydia Hopkins b. 1 June1713 Harwich daughter of Samuel Hopkins and Lydia Rich, and sister to Reliance Hopkins who m. his brother, David. Lydia was a fifth generation descendant of Stephen Hopkins of the Mayflower. Lydia was admitted to the Harwich First Parish Church, 14 July 1734. In 1749 she was named in the Will of her father. Lydia was dismissed from the First Parish Church of Harwich to the parish presided over by Rev. Elisha Kent in the "oblong" valley, Dutchess County (that portion that is now Putnam), New York, 3 Sept 1749 along with many other relatives. Joshua and his family removed to the Philipse Patent in Dutchess County, New York in a section known as Fredericks Precinct, later Frederickstown and East Phillippi and finally after the formation of Putnam County as Southeast. He first appears on the 1747 tax list. When the farms were surveyed in 1754 tenants on lot 8 were David and Joseph Crosby and again 1 May 1768 David and Joseph Crosby. Since there is no known Joseph Crosby and the name Joshua is not found elsewhere in these lists, he evidently was named in error as Joseph Crosby with his brother, David. Joshua is on a list of tax inhabitants of Philipsi Patent, Fredericks Precinct in 1777. The East Phillippi Church records relate that "Mrs. Lydia wife of Mr. Joshua Crosby died 19 Sept 1781 ae 67 years." Her marker of the same date and age is in the Sears Burying Ground, Doanesburg, town of Southeast, Putnam County, New York. Joshua m. 16 May 1784 at Harwich, Massachusetts, (2) Eunice Freeman Foster b. 25 Nov 1705 Eastham, Massachusetts daughter of Constant and Jane Treat Freeman. Record of intention calls him Joshua Crosby of Dutchess County, New York. They returned to Dutchess County after their marriage. Joshua was a member of the church at East Philippi (now Southeast), 4 Sept 1786. His Will dated 8 June 1785 Frederickstown, Dutchess County, left property to wife, Eunice and estate divided among sons, Nathan and Josiah, with legacies to their brothers, Reuben, Joshua, Theodorus, Samuel, and John and their sister, Lydia Foster. Executors were sons, Reuben and Theodorus, and David Crosby Jr. Will proved 16 Dec 1795 filed at Poughkeepsie, New York, he perhaps having d. just prior to that date. In the 1790 census of Frederickstown, there was himself and one female in his household.
21. Nathaniel Crosby b. 1 Nov 1734 bpt 3 Nov 1734 Harwich, Massachusetts.
22. Reuben Crosby b. 1 Jan 1735/6 bpt 11 Jan 1736 Harwich.
23. Joshua Crosby Jr., b. 30 Dec 1737 bpt 29 Jan 1738 Harwich.
24. Theodorus Crosby b. 19 Dec 1739 bpt 23 Dec 1739 Harwich.
25. Elijah Crosby b. 7 June 1742 bpt 11 July 1742 Harwich.
26. Hannah Crosby b. 25 Oct 1744 d. Mar 1757 13y (ts) Sears Burying Ground.
27. Lydia Crosby b. perhaps c. 1746/7.
28. Samuel Crosby b. c. 1749.
29. Josiah Crosby b. perhaps c. 1752.
30. John Crosby b. c. 1755/8.
4. Isaac Crosby b. 18 Oct 1719 bpt 20 Sept 1724 Harwich First Parish Church, Harwich, Massachusetts son of Eleazar Crosby and Patience Freeman m. 7 Oct 1742, Mercy Foster b. 29 July 1722 daughter of Chillingsworth Foster and Susanna Gray. Isaac is said to have been the first Crosby in Dutchess County (that portion that is now the towns of Patterson and Southeast, Putnam County), New York perhaps as early as 1743, which may account for the fact that none of his children were recorded in the Harwich church records. He is on the tax list of 1746 and still there in 1757. He was named in the Will of his father dated 23 Oct 1759. Deacon Chillingsworth Foster left a Will dated 30 Sept 1763 in which he remembered his daughter, "MercyCrosbie." Isaac is related to have been the first elder in the East Philippi Church at Southeast. He appears on the 1777 tax list of Phillippi Patent, Southeast Precinct. Enumerated in the town of Southeast, Dutchess County in 1790, one of only two Crosbys in Southeast the other being his presumed son, Obadiah. There were twenty three Crosbys enumerated in Frederickstown in 1790. There were 3 males over sixteen, 2 males under sixteen, and six females in his household. His wife could not be the mother of the children under sixteen and perhaps a married child with children was residing intheir household. There was a dwelling house listed for an Isaac Crosby, 1 Oct 1798, town of Franklin, Putnam County. He left no Will. His marker stands in the old Milltown Cemetery, town of Southeast and reads, "Isaac Crosby died Feb. 17,1815 in 97 year of his age." His death was also recorded in the Southeast Church records. Beside his marker stands the marker of his second wife, "Thankful Crosby died Feb. 19, 1815 aged 87 years." Her death is also recorded in the Southeast Church records with the same date and an age of 88 years. Milltown is located on the Croton River near the middle of the Oblong. The older children of Isaac were by his first wife, Mercy, and perhaps the younger children were by his second wife, Thankful.
31. Solomon Crosby b. c. 1749.
32. Jerusha Crosby b. 29 June 1754 Southeast m. Eleazar Benedict.
33. Mary Crosby m. John Wilcox.
34. perhaps Obadiah Crosby b. 1760 Patterson.
35. Eleazar Crosby b. 1761.
36. perhaps Elisha Crosby b. c. 1762.
37. perhaps Isaac Crosby b. c. 1765.
38. Sylvanus Crosby b. c. 1769.
39. perhaps Lemuel Crosby.
40. perhaps Darius Crosby.