My grandmother lived on the same block for my entire life, the 400 block of Calvert Street in Chestertown, Maryland. It’s a small strip of affordable housing that is mostly inhabited by Black families and has been for much of the town’s history.
She was one of the few white people who lived on Calvert Street. As a mixed-race child, this stood out to me for as long as I can remember. She never spoke of the history that once existed outside of her front door, and she wasn’t alone. During that time, local Black history wasn’t something that was highlighted or recognized. This erasure was also assisted by the fact everything surrounding her neighborhood had been “built up” — the rural term for gentrification. With that, it became even easier to keep the town’s glowing Black history dimmed and nonthreatening to the white gaze.
The fact that Chestertown still remains predominantly white — 71% of the population while Black residents make up 22% — makes it easy to see how Black history is forgotten and ignored and, in some instances, erased completely.
Black legacy is often undocumented, hiding the rich influence we’ve had on the world at large and the direct neighborhoods that have housed our families for generations. Across America the men and women who fought to provide spaces for Black people to be in community and advance their future always felt the desire for equality and human dignity many white people looked to rob us of.
The nature of small towns makes it easy to suppress and keep sordid histories inaccessible in just a few generations. My father spoke to me about the microaggressions I’d face being Black, and my maternal grandmother simultaneously exhibited some of the behaviors he was talking about, showing me how close to home these attitudes landed.
The nature of small towns makes it easy to suppress and keep sordid histories inaccessible in just a few generations.
These days, downtown Chestertown’s High Street and Cannon Street are home to small businesses, a courthouse, and a few eateries, mostly occupied by white residents and business owners. But this area was once a high-traffic trade destination, now remembered as the Port of Chestertown Marina, home of a large-scale slave trading operation through the Middle Passage. A few feet up the street from this landmark stands 101 Spring Avenue, a recently discovered safe house on the Underground Railroad that can be traced back to enslaved person Isaac Mason from his 1893 memoir, “Life of Isaac Mason as a Slave.”
Less than a mile from these two landmarks is another history that was also concealed for decades.
In a town where your future was mostly determined by what your parents did, my classmates looked to own farms, become bank tellers, or survive off whatever job would provide enough for them to get by. So, it wasn’t a surprise that, growing up, I was laughed off when I presented artistic dreams that seemed too grand for the confines of a small-town mind. Most people of notoriety from Chestertown gained success from politics or sports, so making a living off of music in any way was never even seen as a possibility. And yet, throughout my entire childhood, I was playing, dancing, writing, and dreaming just a few feet from what was once that reality, inhabited by some of the world’s most famous musicians.
After 22 years of living in and around Chestertown, I first got a hint of this other history on August 14, 2014, just a few short months before I would leave my hometown to relocate here to Baltimore City in hopes of chasing a career in music. That day, the town celebrated its very first Legacy Day, an annual celebration highlighting the forgotten and often ignored Black history of the town. The first honoree was the entrepreneur and community leader Charlie Graves, who ran the Uptown Club, which brought renowned entertainers from the Chitlin’ Circuit to our small corner of the Eastern Shore for 42 years.
The Chitlin’ Circuit came to prominence in the 1930s on the tail end of Black Vaudeville shows which were popular in the United States beginning in the 1880s. Performance venues ranging from the mid-Atlantic, Midwest, and Southern regions hosted Black comedians, actors, and musicians in the age of segregation. In 1945, Graves, a U.S. Army sergeant, opened the Uptown Club, where iconic musicians such as Little Richard, Chubby Checker, Etta James, and James Brown all played.
The Uptown Club, which Graves ran with his wife, Hilda V. Lively, was much more than a club. It also acted as a restaurant, bar, billiards hall, and package store. Graves’ other bar, the Concrete Club, was a Black yacht and country club, which also became an after-hours location for the Uptown Club.
“There was kind of two cultures there,” Monica Graves-Bently, daughter of Charlie Graves, said in a 2020 interview. “You had all of the people that worked in Chestertown worked somewhere else, so they either worked in Delaware or they worked in across the bridge in Baltimore or Annapolis. So, when they got off from work and came back home, that was like a meeting place.” The club that got its name from being located on the upper end of the Black area of town consistently rotated patrons through its doors. “On Friday nights and Saturday nights, that’s where everybody in the community went to, you know, just to have fun, to drink, laugh, play cards, shoot pool, do whatever they wanted to do just to relax.”
From adults who were old enough to enjoy the festivities to the neighborhood children, the Uptown Club became a must-see spot for everyone. The youth of the Santiago neighborhood would sneak into the club through the back door to get a peek of the hot spot, The Kent County News wrote.
“I can remember when James Brown’s bus came up Lynchburg Street, pulled up in front of our house, backed up and parked. Mom and her friends dressed up and went to Charlie’s, and the last words out of their mouths were: ‘Now don’t you come around that corner,’” Sylvia Frazier, who would later lead the 100 Voice Choir, recalled in “Here on the Chester,” a book of reflections of Washington College alumni, cited by My Eastern Shore. “So we waited until she got in there good, and we went on in, and crawled in through the crowd on our hands and knees, got our peek and went back home.”
When acts like James Brown, the Impressions, and Little Richard came to town, they interacted with the Black townsfolk as if they were born and raised in the same circle. “The entertainers, before they got really big, were like ordinary people, and they associated with town-people like they always knew you. Remember when Little Richard came to town and needed a hairdo? He refused to go on stage without the hairdo. So, Ms. Marion Lindsey did his hair,” Rosie Herbert recalled in “Here on the Chester.”
But aside from providing entertainment, Graves insisted that the club could also directly assist in the fight for equal rights and racial justice, opening his space for union meetings. He also personally advocated for voter registration in the ’60s and ’70s and would drive voters to the polls and offer lunch specials in the restaurant for voters as they waited.
In some ways, the successes of the Civil Rights Movement spelled the end of the Uptown Club. Following the Civil Rights Act of 1964 which ended segregation, the string of clubs that made up the Chitlin’ Circuit and kept Black people, music, and culture safe and protected for so long began to diminish. In 1988, after being a staple in the community for 42 years, Graves collaborated with the town of Chestertown to demolish the club and use the location for affordable housing. It was another way for Graves to support his community.
Although his contributions were monumental for the time and location, the fact that Graves was a Black man was enough to keep the history suppressed from local documentation for decades. White narrators often have control over the legacy passed down generation to generation and don’t see the importance of the value Black people added to the infrastructure of the communities they lived in.
If Chestertown’s Black history had been revealed to me earlier, it may have evoked a different sense of pride in my hometown. But it’s easy to be disinterested in your surroundings growing up when you’re rarely able to see yourself reflected in the community or history. As a teenager and into my early 20s, I became involved in advocacy and diversity groups that were forming locally in order to change the narrative and better reflect all the inhabitants of the town.
The first Legacy Day honoring Charlie Graves in 2014 had a snowball effect for Black residents of Kent County to learn more about the ways their lineage advanced the areas of town that many Black people are still ostracized from to this day. Much like the movement he helped support, Graves also made a way for Black people in Kent County to see a better life.
But Graves’ legacy at the Uptown Club was also an inspiration for me as I left the Shore and embarked on a musical career. I now knew that my small town wasn’t as small or as white as I once thought. I knew that, just up the way from my grandmother’s front door, there was a club where Black people performed and danced and fellowshipped with love, no matter what harsh realities waited for them outside of that small familiar oasis. The legacy that Charlie Graves leaves behind is one of pride, community, and looking out for your people. The intersection of identity and community and having pride in both is something I will always carry from him.