Nicole Carpenter, left, programs and collections director of the Westport Museum for History and Culture, on Saturday led a Hidden Black History tour, relating facts about the history of Black lives in Westport largely unknown to most residents. / Photo by Gary Webster

By Gretchen Webster

WESTPORT — The hidden history of Westport’s Black residents encompasses enslaved people, slaveholders, a community of more than 70 Black families and, sometimes, a legacy of racism and indifference by white residents to the plight of African Americans who lived or worked in town.

That history, recounted in two walking tours Saturday by the Westport Museum for History and Culture, was chronicled in observance of Juneteenth on Sunday, June 19. The day — now a federal holiday and state holiday — commemorates June 19, 1865, when the last enslaved people in the U.S. were released in Texas, more than two years after President Abraham Lincoln issued the Emancipation Proclamation.

“It’s important to know the history, the roots of our people,” said Donald duBoulay, who was on the tour. “It gives you a sense of belonging. It’s important to know that we belong, that we have roots,” he said.

Above: Alie and Donisha Diagne, Westport residents for 13 years, took their children Leyla and Bilal on the Saturday tour. / Photos by Gary Webster

Left: Jay Norris, a Westport resident for six years, was on the Hidden Black History tour with daughter, Sophia, 5, and son Jacob, 10. Norris said he was surprised to learn the percentage of Westport residents who are Black has declined over the years. “We have some work to do,” he said.

The tour, led by Nicole Carpenter, programs and collections director for the museum, was full of surprising information that many Westporters likely don’t know about local history of the town, including:

  • Westport’s Black residents once represented about 6 percent of the population, but today comprise only about 1 percent of the town’s population. 
  • Slaveholders in Westport included prominent families whose names are still familiar, such as Staples, Jennings, Coley, Jesup and Sherwood.
  • Connecticut was called “the Georgia of the North” by the abolitionist Frederick Douglass because many Connecticut residents supported the Fugitive Slave Act, which required runaway slaves be returned to their owners, even if they had traveled to free states.
  • Although there was some slave trade in Westport, most slaves were brought to town by land routes, not by sea. But a large slave-trading port was located in New London where men and women were brought directly to Connecticut from Africa. 
  • In the 1950s, at least one Westport elementary school staged plays with white children in blackface.
A brick-paved walkway at the Westport Museum for History and Culture captured the attention of those taking the Hidden Black History tour of Westport on Saturday. The walkway lists names of more than 200 known Blacks who lived in Westport, including both enslaved and free. / Photos by Gary Webster

One of the most interesting features of the tour occurred when the dozen people on the tour were taken down an alley at 22½ Main St. The alley leads to the spot where a once busy community of Black residents lived — property that now houses Bedford Square and a parking lot.

Black residents’ homes were located behind Main Street and were not labeled with whole numbers, Carpenter explained, but with half numbers. “Main Street 22½” became known as the name of the Black community.

The area, with about 70 Black families, existed until 1949 when Mrs. Rosco Johnson, who acted as a spokesperson for neighbors, asked the Representative Town Meeting to repair a boarding house in the neighborhood. 

The Hales Court housing project was being built at the time for returning World War II veterans, and Johnson told the RTM that some boarding house residents were veterans and should be allotted housing at Hales Court, as she also sought help with repairs for boarding house residents.

The boarding house, however, burned down shortly after the RTM session in what was most likely a fire bombing, Carpenter told the tour, and not one of the Black residents were given housing at Hale’s Court. The Black community of Westport began to shrink then, with many of the families moving to Norwalk or Bridgeport, she said.

Saturday’s tour concluded at a brick-paved walk in front of the history museum’s building at 25 Avery Place, with names of more than 200 both enslaved and free Black residents who once lived in Westport etched on the walkway’s stones. Some of the stones carried names of one person or a family, found through historical research by the museum staff; other stones said “free person” after a name or just simply said things like, “Negro child.”

People crowded around the paved walk, reading the names.

“I’ve learned a lot about the town and the African American people who were here,” said Althea Seaborn, a member of TEAM Westport a town advisory committee on topics of diversity, equity and inclusion. “It’s comforting to hear that some of them were free and going about their lives.”

Jay Norris, a Westport resident for six years, said he had heard there never had been much diversity in Westport, and it was interesting to find out that a sizable Black community had once existed here.

“It’s touching for me to hear that there were Black people in this town, even if they were enslaved — but they were here,” he said after the tour. 

“They were six percent of the population then, and are one percent now — we have some work to do.”

Gretchen Webster is a freelance writer and frequent contributor to Westport Journal. Learn more about us here.

Paige and Ted Parker focus on the Hidden Black History tour organized by the Westport Museum of History and Culture on Saturday in observance of Juneteenth.
Althea Seaborn said she learned a lot on the Black history tour. “I wish I had taken this earlier.” / Photos by Gary Webster