Sherwood Haywood was born 1762 in North Carolina, the 6th of 10 known surviving children (4 boys/6 girls) born to Col. William Henry Haywood Sr. and his wife, Charity Hare. Reports vary as to whether he was born in Edgecombe County or at Conecanarie, Halifax County, NC.

Sherwood is descended on both sides of his family tree from prominent and early settlers of North Carolina. His was the paternal grandson of the family patriarch, John Haywood, and his wife, Mary "Lucy" Lovett of Edgecombe County. John Haywood was born in Christ Church Parish, near St. Michael's, in the Island of Barbadoes. He was the son of John Haywood, a younger brother of Sir Henry Haywood, a Knight and magistrate in the old country. The family patriarch settled in 1730 at the mouth of of the Conecanarie in Halifax, then a part of the great county of Edgecombe. He was Treasurer of the northern counties of the Province from 1752, until his death in 1758. Sherwood's father, William H. Haywood Sr (1772-1779) served as a Colonel in the Revolutionary War and was a member of the Provincial Congress at Halifax in April 1776; and was one of the Committee to form the State Constitution and was appointed a member of the Council of State. On his mother's side, he is the maternal grandson of Moses Hare Sr, who settled in Chowan County, then later Gates County, NC.

Sherwood was 33 years old in 1795 when he married 19-year old Eleanor Howard Hawkins, daughter of wealthy planters, Philomen Hawkins III and Lucy Davis of "Pleasant Hill" Plantation in Granville County, NC.

The couple would reside in Raleigh, Wake County, from where Sherwood managed his 3 NC plantations, with over 250 slaves, and where he served as clerk of the North Carolina State Senate (1786-1798); and later as an agent for the Bank of Newbern in Raleigh.

The couple became parents to 9 known children: Nancy Ann Hawkins Haywood (1796-1825), Sarah Lee (1799-1880), William Rufus (1801), Lucy Davis (1805), Delia (1807-1876), Francis Philomen (1809-1900), Robert Williams (1812-1869), Maria Toole (1815-1906), and Dr. Richard Benneham Haywood (1819-1889).

Sherwood Haywood died in 1829 at age 67. His wife of 34 years survived him another 26 years, passing in 1855 at age 79. They are buried near each other in Old City Cemetery, along with some of their children.