From its earliest years, Midway was home to an ambitious and prosperous African American population. Many black citizens owned their own homes in the 19th century, a tradition that continued in the 20th century. In 1834 a former slave founded the town’s still-operating Second Christian Church, the oldest black congregation of the Disciples of Christ denomination in Kentucky, and 20 years later two members of the local St. Matthew’s African Methodist Episcopal Church purchased a city lot for its sanctuary. The Midway Colored Independent Order of Odd Fellows chapter boasted 94 members as early as 1879.
Midway’s African American commercial district appears to have been located on one side of Railroad Street near the train tracks. Passing through town, Helen Morrison focused her camera on men standing or walking on the sidewalk in front of several businesses. She took compelling images of an elderly gentleman walking away from the Skylark Tea Room, a man standing in the doorway of a shoe repair shop, and a man wearing overalls and a hat with the shoe repair shop in the background.
A “7 Up” sign visible in one image helps date Morrison's visit to Midway. The soft drink’s manufacturer introduced this shortened product name in 1936, ruling out the possibility that Morrison took these photographs in the town during her first Kentucky trip in 1935.