Over 200 years ago, hundreds of enslaved people lived in the area that would become Westport.

They worked as farmhands, apothecaries, sailors, millers, coopers, blacksmiths and more. Among them were Tim, who was owned by Capt. Joseph Bennett, a Revolutionary War veteran and Tim’s wife, Lill, owned by the Disbrow family.

For a time the couple lived apart — Tim at the Bennetts and Lill at the Disbrows with their children. In 1794, Joseph Bennet buys Lill and the family is reunited. By 1799, they were emancipated.

Tim, Lilll and their children, including a set of twins, moved to upstate New York where some of their descendants, including Kyle Bass, their sixth-generation great-grandson, still live today. Bass returned to Westport recently to take part in a ceremony at Westport Historical Society which has memorialized the names of Westport’s enslaved people in its brick walk.

A playwright, Bass is writing a play that tells Tim and Lill’s stories to illustrate a broader picture of slavery in New England, a region commonly misperceived as free for African Americans.

Bass’ project focuses on unknowns in Tim and Lill’s story, such as their roles in the War for Independence. As members of a Revolutionary household, they likely experienced the British march to Danbury in April 1777. Tim may have witnessed British regulars marching past the Bennet house which still stands today at 96 Compo Road S.

Once free, the couple moved to New York but questions linger: What happened to their daughter, Nancy, who seems to have disappeared from the Greens Farms Church log book where enslaved people were listed among births, marriages, baptisms and deaths? And what more of David Judah, the patriarch of one of Westport’s first Jewish families, a justice of the peace, who signed the Bennets emancipation papers?

By piecing together the story, Bass hopes to illuminate complicated stories of his own family and of African Americans in the North as well as a hidden part of Westport’s past.

Westport Historical Society has been a cultural and educational organization dedicated to preserving, presenting and celebrating the history of Westport since its founding in 1889. More information can be found at westporthistory.org