David Hempstead Sr.

When David H. Hempstead Sr. died in November 1843, he was described in a Sag Harbor newspaper as a longtime Shelter Island resident and “an old and respectable Colored Man.” At the time of his death he was also the owner of a 95 acre farm near West Neck on Shelter Island. Owning the farm was the culmination of a long life of work.

David Hempstead was born into slavery ca. 1774 in Southold, NY. He was enslaved by Thomas Hempstead (1732-1805), the son of well-known Southold resident, Robert Hempstead. Research is still under way to determine who David’s parents were and what their circumstances may have been.

According to the 1804 Last Will & Testament of Thomas Hempstead, David was granted his freedom and the gift of $10. From Southold he made his way to Shelter Island where he lived and worked for the rest of his life. He is listed on the U.S. Federal Census of 1810 as a Free Man of Color and the head of his household. From this time onward his name appears frequently in account books and Shelter Island records. He worked at Sylvester Manor for Sylvester Dering and following Dering’s death in 1820, David worked for his widow Esther Sarah Dering as her farm manager from 1825-1827. The agreement between them states that David is to have half shares of all the wheat and crops grown on the Manor farm, the use of a house for him and his family and a horse for his personal use. Esther Sarah depended on David and his sons to manage the property and her accounts are full of the work he provided. David’s services included harvesting wheat and taking it to the mill, slaughtering livestock, cutting wood and many other day to day workings of the farm and property. These accounts are unique in that Esther refers to David and the other people of color working for her simply by their names without the qualifiers that were often used to identify them: “Colored,” “Negro” or “Black.”

Embarking on their own lives, David Hempstead Jr. and his sister Esther Hempstead Green left Shelter Island for Sag Harbor to become residents and homeowners of the Eastville community and founding members of St. David’s AME Zion Church ca. 1839. David Sr. may also have become a member of the new unsegregated church in Sag Harbor. 

It was after a visit to his family in to Sag Harbor that he fell overboard from the ferry between Shelter Island and North Haven and drowned. In addition to the notices in the local newspapers announcing his death, his farmland on Shelter Island was listed for sale at auction several months later. The location of his grave is not known for certain but if his body was recovered from the water,  it is likely that he was buried in an unmarked grave at Sylvester Manor’s Afro-Indigenous Burial Ground. 

The life path of David Hempstead Sr. from slavery to successful land owner is extraodinary but not unique and is a part of local history of the East End of Long Island that until recently has been relatively unknown and rarely discussed. The evidence of his life can be found and seen throughout numerous historical documents and records. He was a highly respected man of the 19th century; a hard working husband and father who provided for his family and participated fully in his community as a Free Man of Color. We recognize him as a Founding member of this place.

Esther Sarah Dering’s  Account Book, Shelter Island Historical Society

Lawsuit document of Samuel Smith Gardiner vs. Esther Sarah Dering and David Hempstead Sr., Sylvester Manor’s archives