In 1945, former U.S. Army Sergeant Charlie Graves built a multi-enterprise operation on this site that included a nightclub with top-notch décor, a restaurant, bar, billiards hall, and package store. In 1955, he married Hilda V. Lively, and from then on they partnered in the business while raising a family. The Uptown Club became a notable venue on the Chitlin’ Circuit, showcasing Black musicians who endured segregation in the Jim Crow era. From the 1940s to the 1960s, Charlie Graves and the Uptown Club became known throughout the mid-Atlantic coast for hosting artists on their way to iconic fame, including Bo Diddley, Chubby Checker, Fats Domino, James Brown, Jr. Walker and the Allstars, Little Richard, Louis “Satchmo” Armstrong, Otis Redding, Patti LaBelle and the Blue Belles, Ray Charles, Smokey Robinson, and The Platters. In the 1970s, the club booked local cover bands, including The New Breed, Highlanders, Rotations, and The Professors of Soul. In the neighborhood called Santiago, the Uptown Club served as a community hub for union meetings, voters headed to the polls, and jobs. Graves, admired for his daily wear of a suit and wide brim hat, earned respect for his community advocacy and business acumen. In 1988, after 42 years of service, Charlie collaborated with the Town of Chestertown to raze the Uptown Club to make room for affordable housing.