Chestertown has a rich and diverse history. The town was a major port in the colonies, and even has evidence of the slave trade. However, as Chestertown grows and years go on, the equality and the friendliness of the town are kind of falling apart.
Milford Murray, an African American man who was a young child during World War II, grew up in Chestertown. As a young child he remembers how rationing affected his grandmother's cooking. His grandmother would often make apple or peach cobblers, cakes, and other sugary treats, that she would still make during the war but didn't taste quite as sweet. Mr. Murray was happy to talk, and would often compare Chestertown today to what it was like living here as a teenager and young child. Chestertown before and after World War II, was actually a little more close and friendly than it is now. There was a sense of camaraderie, everyone would check on each other, and offer help, assistance, or even offer condolences, if that was needed.
Murray mentions a story of how his grandmother was friends with another grandmother who was a full-blooded Italian. The grandmothers would often sit on the porch and have conservations even though Milford's mother didn't speak a word of Italian, and the other grandmother didn't speak a word of English. They would also send food back and forth, making the younger kids drop it off. The grandmothers simply understood each other, as they had probably went through many of the same experiences. They simply didn't have to talk to each other, they could just be together.
Murray, even after being away for 34 years, he came back to live in Chestertown in 2004. He is now mostly retired, but he often works for the college as a driver.