"It was a real struggle in the late 1800s. Black parents had to buy the equipment and books their teachers and students needed. They had to clean the schools," says historian Linda Rowe of Colonial Williamsburg.
"And whenever something did happen with the black schools, Samuel Harris was usually the one they put in charge."
Despite such obstacles, Harris not only sent his son Samuel Jr. to what is now Virginia State University but also financed his studies at Harvard Medical School, preparing him for a Boston practice and a pioneering role as the first African-American medical specialist in the nation.
Daughter Elizabeth received an unusually advanced education, too, but died just a year after her marriage to prominent Hampton Institute administrator Robert Moton, who later succeeded Booker T. Washington as president of Tuskegee Institute.
"You can tell a lot about a man by what his children do," Kale says. "And his children were amazing."
Harris' black friends and acquaintances provide similar kinds of insights into the life and character of the former slave.
Like brothers Daniel and Frederick Norton of York and James City counties — who served prominently in the General Assembly during Reconstruction — most were men of education, property and influence. They also knew how to command respect from whites by working within and sometimes dramatically pushing the limits of the system.
"He was always extremely well-dressed. As you can see from his picture, he seemed determined to out-proper the most proper whites," Hardy says.
"I think it was a way for enterprising blacks like Harris to distance themselves from the past and proclaim their equality — because they knew it wasn't going to be handed to them."
Such hard-won and sometimes grudging regard began to fade after the passage of the Virginia Constitution of 1902, which stripped most blacks of the right to vote and rolled back many of the gains of Reconstruction.
But the short, dapper shopkeeper remained so highly esteemed that thousands of mourners both black and white attended his funeral service at First Baptist Church when he died in his early 50s just two years later.
"In the death of Samuel Harris the town has lost one of its most progressive and enterprising citizens," wrote editor W.C. Johnson of the Virginia Gazette, mourning the loss of his biggest advertiser and frequent subject of news articles.
"His removal from us is a distinct loss, not only to his family, but his town."