Squeezed in between Union and Church street sits a little alley that is rich with history. George Michael Deaderick, a former Virginia planter and businessman, donated land to the city of Nashville in the late 1780s that would become Printers Alley. According to Louis Littleton Davis' Nashville Tales, his intention was to provide a service entrance for the buildings being constructed along College and Cherry Streets (now Third and Fourth Avenues) while fostering goodwill in his adopted hometown. In the early days of Printer's Alley, over twenty different publishing companies operated here ranging from general publications to newspapers.
By the early twentieth century, the Alley had turned into a hotspot for nightclubs and bar life. Early in Nashville’s brown bag age and prohibition age, the city’s first bars in appeared in Printer's Alley. “Printer's Alley was Nashville's dirty little secret. It didn't matter what you were looking for, you could find it there. Nashville's politicians and police protected the Alley even after the sale of liquor was outlawed in 1909.”
Hilary House, elected Mayor at the time, was quoted by reporters at the time as saying, “Protect them? I do better than that, I patronize them.” He was mayor for twenty-one of the thirty years that the sale of alcohol was illegal. In 1939, Nashville repealed prohibition and made it legal to buy liquor in stores. For the next thirty years The Alley flourished as the Mixing Bar came into existence.
Over time the idea of “alley” gained a negative reputation and crime increased as legal businesses abandoned the area. Eventually, only a few bars and clubs remained.