This family is of German origin and first settled in Pennsylvania where the records show the following:
Penn. Archives, 6th Series, Vol. 6, page 200.
German spelling Woolwine....Wohlwen....Wollwein
Records of Egypt Reformed Church....Lehigh Co. 1734-1834 - pub. 1905:
Children baptized, names of parents and names of sponsors.
1. Wohlwein, Johannes, son of Philipus and Elizabeth, born 4/24/1767; sp. Johannes Meyer and Catharine Schafer; both single.
2. Wollwein, Barbara, Daughter of Felip and Elizabeth, born 2/7/1769; baptized 3/5/1769; sp. Marx Binckle and Barbara Pulmann. (Penn. Archives, 6th Ser. Vol. VI Page 200).
Philip Woolwine's name does not come into the records again until 1782 when the Virginia Census credits him with living in Frederick County, Virginia, and having in his family ten white persons and one black.
Philip and Elizabeth Woolwine, Sr. removed from Pennsylvania to Winchester, VA. Land record contracts from the year 1774 thru 1785 are on record in the Clerk's Office, Frederick County Circuit, P.O. Box 573, Winchester, VA 22601. During this period their children were probably born in the Colony of Virginia or Winchester, Va.
In 1785 the family removed to Staunton, Va. Philip died October 1786. The administration of his estate was granted to his wife, Elizabeth. Sales Bills for the Estate recorded September 1787 in Augusta County Clerk's Office, Staunton, Va., Will Book 7, Page 25. It is presumed he is buried in Stanton, Va.
Chalkley-Chronicles of the Scotch-Irish Settlement in Va., Vol. 1-2-3 show the following children: Elizabeth, Philip Jr. who married Elizabeth Harris, Susana, Jacob, William, George. The first two children born in Pennsylvania.
Elizabeth Harris's declaration for a pension shows a different birth date. It is possible that Philip Jr. was born in Pennsylvania.
The book "Virginians in the Revolution" Historical Register of Virginians In the Revolution, sailors, marines, soldiers 1775-1783, by John H. Gwathmey, page 847 list:
Woolwine, Philip, wife Elizabeth aided in Frederick 1779.
Philip S. Woolwine, Jr. (1766-1850) entered service of the Revolutionary war as a volunteer from Augusta County, Virginia. His place of residence during the Revolution was Staunton, Virginia. He served for about six months and was honorably discharged. Philip joined near the middle or end of the war. He spoke of being at "the Point", probably Stoney Point. Officer: Perry. He was added to the New Ancestor Records section of the Daughters of the American Revolution magazine February 1972 edition. Copies from copies of affidavits from National Archives on Military Service, by his wife Elizabeth and son Jacob. Historical Register of Virginias In the Revolution, soldiers, sailors, marines - 1775-1783. By John H. Gwathmey. Page 847.
Jacob Paxton Woolwine, oldest son of William Herbert Woolwine, went into the Southern (Confederate) Army for his father on the Jefferson Davis first draft. In 1864 the South found that William was not in the Army, so he was again drafted into the Southern Army.
1850 Monroe County, Virginia census:
| Family No. | Last Name | First Name | Age | Gender | Occupation | Born |
| 451 | Woolwine | William | 36 | M | Farmer | Virginia |
| Rebecca | 36 | F | ||||
| Lewis W. | 15 | M | ||||
| Martha F. | 12 | |||||
| Fleming I. | 10 | M | ||||
| 207 | Woolwine | William | 27 | M | Laborer | Virginia |
| Frances | 22 | F | ||||
| Jacob V. | 5 | M | ||||
| George W. | 3 | M | ||||
| 483 | Woolwine | Henry | 26 | M | Farmer | Virginia |
| June | 21 | F | ||||
| Mary C. | 4 | F | ||||
| Amanda J. | 2 | F | ||||
| 432 | Woolwine | Jacob | 47 | M | Farmer | Virginia |
| Mary | 46 | F | ||||
| James | 22 | M | Laborer | |||
| George | 17 | M | ||||
| John | 19 | M | ||||
| Jacob | 14 | M | ||||
| Harriet C. | 12 | F | ||||
| Henry H. | 9 | M | ||||
| Wesley L. | 5 | M | ||||
| 133 | Woolwine | Evaline | 42 | F | Virginia | |
| Phillip J (?)* | 86 | M | Carpenter | |||
| Elizabeth** | 85 | F | ||||
| Ann | 22 | F | ||||
| William | 20 | M | ||||
| Philip | 18 | M | ||||
| *Died Nov. 13, 1855. Monroe County, Virginia | ||||||
| **1860 Monroe County, Virginia census shows Elizabeth 95 years. | ||||||
| Philip Jr. and Elizabeth Harris Woolwine, parents of Jacob Woolwine. | ||||||
LITERARY SCHOOL RECORDS, Monroe County, Virginia (now West Virginia):
| Year | Pupil | Age | Parent |
| 1852/3 | Henry Woolwine | 11 | Jacob Woolwine |
| Harriet Woolwine | 13 | Jacob Woolwine | |
| 1853/4 | Jacob Woolwine | 17 | Jacob Woolwine |
| Harriet Woolwine | 15 | Jacob Woolwine | |
| Henry H. Woolwine | 12 | Jacob Woolwine | |
| Paxton Woolwine | 9 | Jacob Woolwine | |
| Wesley Woolwine | 10 | Jacob Woolwine | |
| George W. Woolwine | -- | Jacob Woolwine | |
| 1854/55 | Mary C. Woolwine | -- | Henry Woolwine |
| Sarah F. Woolwine | -- | Henry Woolwine | |
| 1828/29 | Maria Woolwine | -- | (Believed to be the daughter of Philip Sr.) |
| 1834/35 | Ann Woolwine | 11 | Mrs. Woolwine |
| William Woolwine | 8 | Mrs. Woolwine | |
| 1837/38 | Ann Woolwine | 13 | Eveline Woolwine |
| Henry Woolwine | 15 | Eveline Woolwine | |
| 1838/39 | William Woolwine | 12 | Jacob Woolwine |
| Eliza Woolwine | 12 | Jacob Woolwine | |
| 1841/42 | William Woolwine | 16 | Jacob Woolwine |
| John Woolwine | 11 | Jacob Woolwine | |
| George Woolwine | 8 | Jacob Woolwine | |
| Elizabeth Woolwine | 14 | Jacob Woolwine | |
| James Woolwine | 12 | Jacob Woolwine | |
From the notes of C. W. Woolwine, grandson of Jacob S. and Mary Harmon Woolwine:
"The War split up lots of families, some going with the North and some going with the South, and this happened to the Jacob Woolwine Family. In 1861 war broke out, Grandfather (Jacob S. Woolwine) was on the dividing line between the North and the South, so Grandfather (Jacob S.) Grandmother (Mary Harmon) and my Father (Wesley Lomas Woolwine) were moved over to Gallipolis, Ohio by General Wertz of the Rebel Army, and then Jake was drafted into the Reel Army as Commissary Man, along with Grandfather's wagon and mule team. Grandfather was not recompensed for the team and wagon. Jake deserted after about 30 days in the Southern Army and joined Custer's Army and was with him during the balance of the War."
Jacob Woolwine buried in Pine Street Cemetery, about 40 feet or so from the entrance (as you go out Pine Street along the right side of the drive between two large trees), Gallipolis, Ohio.
Mary Ann Harmon Woolwine buried in Friendship Cemetery 8 miles north of Hollowell, Kansas