The Gwynn’s Island Project Reconnects the Descendants of Black Island Families to their Roots

Maria S. Montgomery & Allison Thomas
Maria S. Montgomery & Allison Thomas

Maria Montgomery found me on in 2016. Our family trees overlap because my ancestors enslaved hers. We are “linked descendants”—cousins regardless of whether we share DNA. She asked if I had any probate records that might list people my family enslaved on Gwynn’s Island in Mathews County, Virginia, a five-square-mile triangle of land in the lower Chesapeake Bay.

I sent Maria my third great-grandmother Mary T. Edwards’ Civil War diary that lists 20 enslaved people seized as contraband by the Union Navy in 1863. Maria’s great-great-grandparents, William M. Smith (“Billy”) and Dolly Jones (“Young Dolly”,) are on that list.

Page of Civil War Diary June 5, 1863
Page of Civil War Diary June 5, 1863

This diary shocked me: until I read it, I did not know my family continued to enslave people through the Civil War. I warned Maria it was difficult to read, but she replied, all information is good information.

William and Dolly Smith were among the 200 freed people returning to Gwynn’s Island after the Civil War. Over the next 50 years, they bought land, farmed and fished, built a church and a school, and created a community. By 1910, the Smith family was just one of several Black Island families that spanned four generations.

But something changed as Jim Crow ushered in a new century. In 1912 Mathews County residents erected a Confederate monument in front of the court house, and opened a whites-only housing development.

James Henry Smith 1867-1934 Photo courtesy of Rufus & Freddie Frazier
James Henry Smith 1867-1934 Photo courtesy of Rufus & Freddie Frazier

Maria told me that her great-grandfather James Henry Smith was found guilty of felony assault against two white men on Christmas Eve of 1915. This incident caused the family to leave the Island in disgrace.

But the Smiths weren’t the only ones to leave: most of the Black families left by 1918, and within two years the remaining five households left. Local histories written by white people claim that Black families left gradually to seek new jobs; local Black residents said the Island Black community was “run off.” We wanted to find out what really happened.

Maria and I spent two years reviewing newspapers, court records, property deeds, census records and genealogical information to figure out what happened. When COVID hit, we hired a local researcher to keep digging. No first-hand accounts existed, only the stories of white descendants with much to hide.

We were appalled to find trial records, “mis-laid” in a dead papers file, that showed that James Smith was innocent. The judge believed Smith acted in self-defense, and gave him a light sentence for both felonies, only 30 days in jail and $45 in fines. The disgruntled white Island community then threatened to lynch Smith when he was released from jail. Escalating violence frightened the entire Black community, and many packed up and left immediately.

Our outrage grew when we discovered that just two months after the trial, a white trial witness purchased Smith land. Was this a reward for his false testimony?

The Smith family was likely targeted because they were community leaders, and the largest Black landowners on the Island. By 1922, local white men had snapped up most of the Black-owned land. These transactions were legal, but the sellers signed the deeds from other counties. They had abandoned their homes years earlier.

James Smith moved his family to Norfolk to a series of rental homes, no longer an independent farmer but a coal trimmer, shoveling coal on the docks. He died at age 66 of a stroke. The white man who purchased Smith’s land lived on Gwynn’s Island until his death at age 97.

As I trace the fate of these families after they fled Gwynn’s Island, I cannot ignore the trauma that permeates the census records and death certificates. The legacy of enslavement, and the role played by my family, hurts my soul. These Black families lost their land, their vocation, their community, and, often, their health and well-being.

How does one begin to repair this harm? Maria wants to exonerate James Smith. Telling the truth about the events of Christmas Eve 1915 is a start. The Gwynn’s Island Museum has also agreed to publish a revised history. The Gwynn’s Island Project website, created with Sharon Morgan and Our Black Ancestry, not only corrects the record, but will reconnect Black descendants with their roots on Gwynn’s Island. Families scattered primarily to Hampton, Virginia, as well as Baltimore, Washington, DC, Philadelphia, and New York City. Common surnames, in addition to Smith, were Booker, Coleman, Creighton, Frazier, Gayle, Hayes, Jackson, Johnson, Jones, McKnight, Peachey, Perley, Respess, Roy, and West.

The trauma of these events for Black families has meant that few stories have been passed down of life on Gwynn’s Island or of the events that precipitated the exodus. Perhaps these first reparative actions will unlock more.

The Gwynn's Island Project ( Designed by Sharon Morgan, Our Black Ancestry
The Gwynn’s Island Project ( Designed by Sharon Morgan, Our Black Ancestry

Author: Allison Thomas

Allison descends from enslavers dating to colonial Virginia (Carter/Gwynn/Braxton). In addition to editing Bittersweet, she serves on the Steering Committee of the Southern California CTTT chapter, and the Local Affiliate Working Group. She is writing about her own family as well. In normal times, is a film/theatre producer.

15 thoughts on “The Gwynn’s Island Project Reconnects the Descendants of Black Island Families to their Roots”

  1. This story of intimidation, injustice and their long term effects makes me grit-my-teeth angry. I hope you and Maria and other family members are able to exonerate Mr. Smith, show up the exploitation and racism from the past, and create a more truthful narrative for the Island and for its past residents. Thank you for doing this work.

  2. I am from Mathews and had heard about something occurring on the Island but never got any answers. I truly enjoyed this article! Thank you! Would love to know more!

    1. Are you by chance related to Edmund Filmore Forrest? He was a pastor and landowner on Gwynn’s Island?

      1. I have never heard of EF Forrest. Forrest is my married name. My Dad, John M. Blake was the local garbage man on the Island. He was born in 1919 so he told me that Black people lived on the Island but lost their property. I am anxiously waiting for more stories!

    2. Maria and I will be speaking at the Middle Peninsula African American History and Genealogy Society on March 31st….they are on Facebook. Join us if you can….and the website has lots more info.

    3. Maria and I are speaking to the MPAAHGS on Sat. Mar 13th. Let me know if you want info…..Zoom of course!

    1. Probably if we dig back far enough! There is a link to a small family tree on the website, and I have a tree on Ancestry.

    2. Maria and I are speaking to the MPAAHGS on Sat. Mar 13th. Let me know if you want info…..Zoom of course!

    1. Hi Jalitzah…If you go to the website ( and click through on the Family Tree, then input Gwynn, you might find some relatives. Arthur Respess was a Black landowner on the Island, his mother was Nancy Gwynn. You can find information on him in the landowning section as well. email me through the website and I can answer more specific questions.

    2. Maria and I are speaking to the MPAAHGS on Sat. Mar 13th. Let me know if you want info…..Zoom of course!

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