Unfortunately "Jackson" is a very common name so it is extremely difficult to connect some of these earlier people conclusively. I have concentrated on Sussex County records since I believe that my earliest ancestors came from there. The earliest JACKSON I have found in Delaware was Cornelius Jackson who appeared in Lewes DE in 1681.

For the earliest mixed-race Jacksons we must look at the records of St. George's Chapel and the Lewes/Cool Springs Presbyterian Church in Sussex County where we find that:

• Jno Jackson , a "mulatto", baptised his son William Jackson at St. Georges Chapel on June 15,1746 and also recorded the birth of his daughter Patience Jackson , born on 25 October 1748. The Lewes/Cool Springs records mention that Patience later married Job Friend, a mulatto, at the home of Mr. McIlvain on 8 June, 1772

• William Jackson and his wife Nelly, recorded the birth of their daughter Lydia at St. George's. Lydia was born 19 October, 1768 and baptised 20 August, 1769. William was called a mulatto in the records. William appears in the 1773 and 1774 Indian River Hundred taxables. He's listed in the 1810 and 1820 Nanticoke Hundred census records as head of a "free colored" household of 4.

• Annanias Jackson and his wife Hester registered the birth of their daughter Hester at St. George's on 10 March 1785. No mention is made of race in these documents but the 1810 DE census records list an "Annias Jackson" as head of a household of 8 free colored persons in Indian River Hundred.

• Per the Lewes/Cool Springs records, Agnes Jackson married Edward Harmon on Nov. 27, 1788, Isreal Jackson married Polly Handsor on Aug. 29, 1802, Hester Jackson married Eli Hitchins on Sept. 9, 1802, and Katherine Jackson married Thomas Hanzor on Feb. 4, 1808.

• James Jackson , a "Poore Muloto & Several in his family" was a deliquent taxable in Indian River Hundred in 1789. He also appears in the 1810 and 1820 census records for Indian River Hundred, listed as "free colored"

• Stephen Jackson appears in the Indian River taxables from 1773 - 1784. He's also listed in the 1810 and 1820 Dagsboro Hundred census records as "free colored".

  From this we can say that:
  

  • John Jackson was the father of William Jackson & Patience Jackson
    
  • William Jackson was the father of Lydia Jackson
    
  • Annanias Jackson was the father of Hester Jackson
    
  • James, Stephen and Annanias were POSSIBLY children of the original John Jackson
    

  The recorded marriages to Handsor, Hitchins and Harmon - names that appear among the current mixed raced community- indicates that as early at the mid 18th century Jacksons were a part of the mixed race Indian community in Sussex County, DE.

  Misc. Jackson Census References in Sussex County, DE

  YEAR	SOURCE	AREA	NAME
  1785	Tax Lists	Indian River Hundred	Samuel Jackson (#1)
  1785	Tax Lists	Indian River Hundred	Samuel Jackson (#2)
  1785	Tax Lists	Indian River Hundred	Stephen Jackson
  1785	Tax Lists	Indian River Hundred	William Jackson
  1785	Tax Lists	Nanticoke Hundred	Peter Jackson
  1789	Tax Lists	Indian River & Angola Hundred	Annias Jackson
  1789	Tax Lists	Indian River & Angola Hundred	Francis Jackson
  1789	Tax Lists	Indian River & Angola Hundred	James Jackson called: "Poore Muloto & Several of his family - deliquent"
  1797	Tax Lists	Broadkill Hundred	Clement Jackson assessed 594 pounds
  1800	Tax Lists	Broadkill Hundred	Clement Jackson
  1800	Tax Lists	Indian River Hundred	Ananias Jackson
  1800	Tax Lists	Indian River Hundred	Israel Jackson
  1800	Tax Lists	Indian River Hundred	James Jackson
  1800	Tax Lists	Indian River Hundred	John Jackson (of Ananias)
  1800	Tax Lists	Indian River Hundred	Nathaniel (?) Jackson
  1800	Tax Lists	Nanticoke Hundred	Peter Jackson
  1820	Federal Census	Indian River Hundred	Ananias Jackson "free colored"
  1820	Federal Census	Broadkill Hundred	Andrew Jackson "white"
  1820	Federal Census	Indian River Hundred	James Jackson "free colored"
  1820	Federal Census	Nanticoke Hundred	Tobias Jackson "free colored"
  1820	Federal Census	Nanticoke Hundred	William Jackson "free colored"
  1830	Federal Census	Broadkill Hundred	Ann Jackson "widow", "white"
  1830	Federal Census	Indian River Hundred	Henry Jackson
  1830	Federal Census	Laurel	Stephen Jackson (N)
  1830	Federal Census	Laurel	Stephen Jackson (N)
  1830	Federal Census	Nanticoke Hundred	William Jackson (N)

  An Israel Jackson is listed as a neighbor of Warren Wright (b.1803) . He and his wife, Mary Jane NORWOOD, are said to have had the following children: Elizabeth, Eugenia, Clementine and Isreal Jackson. After Israel's death, Mary Jane married Elisha Wright , Warren's son.

  My first known Jackson ancestor, however, was Wesley Jackson . I have not yet been able to connect him to any of these earlier Jacksons but a connection is highly likely.