This Was Then: The mailman and the shoemaker’s boy

From delivering mail to delivering slaves to freedom.

Rev. Charles B. Ray, who spent his early years in a Holmes Hole shoemaker’s shop. He became a leading national abolitionist and publisher of the Colored American. - Chris Baer

Forty-three-year-old mail carrier Ansel Dimmick of Falmouth set off one cold January evening in 1816 with mail bound for Holmes Hole. “The sound was much obstructed with ice,” reported the New York Evening Post, “and the passage very difficult and dangerous, and impracticable by small boats.” With him was James Freeman, sheriff of Barnstable County, and Falmouth hatter Amaziah Wilcox. They never made it. Wilcox’s body, the boat, and the mail were found five days later on West Chop, and Freeman’s body was found the next day at Eastville. Dimmick’s body was never found. “All have left widows & large families of children indigent,” wrote the minister who attended their funerals.

But the mail must go through. Appointed in Dimmick’s place in this dangerous job was Joseph Ray, a 37-year-old African-American sailor from Rhode Island, likely born a slave. Ray was by now a professional mariner, holding a Seamen’s Protection Certificate he had been issued a decade earlier. He carried the mail to and from the Vineyard in his open sailboat for the next 30 years, bringing the mail in the worst of weather from Falmouth to Holmes Hole and on to Edgartown. His wife is said to have been an escaped slave who had once been harbored by abolitionist families in Falmouth. Traveling lecturer Samuel Gould wrote of leaving the Vineyard in 1837, “From Martha’s Vineyard I crossed over to Falmouth, with Mr. Ray, an estimable colored citizen of Falmouth. Mr. Ray … has the reputation of being the best navigator in the Sound.”

Not long after he began his job in 1816, Ray placed his son Charles into an apprenticeship with shoemaker Thomas Robinson of Holmes Hole, to labor in his shoemaking shop on the northeast corner of Main Street and what we now call Union Street, formerly known as Wharf Street.

Although later in life Charles was remembered fondly by his white peers from the Vineyard, their memories focused mostly on the leather strap Robinson used to beat him. In 1832 Ray left the Island to become the first black student to enroll at Wesleyan University; however, his time there lasted less than two months, as white students immediately demanded his removal. Charles Bennett Ray would become a leading abolitionist and one of the most distinguished black leaders of his day. He published what was by 1840 the most important African-American newspaper in the United States, the Colored American, and as an active “conductor” of the Underground Railroad, Ray was personally involved in helping Southern families escape slavery. His daughter Charlotte eventually became the first African-American woman to pass the bar and become a practicing lawyer.

Chris Baer teaches photography and graphic design at Martha’s Vineyard Regional High School. He’s been collecting vintage photographs for many years.