Pennytown was the largest black community in central Missouri. Historically, its population consisted of former slaves and their descendants. Its peak population was 1,000 and the final birth in the community occurred in 1944.
Joe Penny was a former slave from Kentucky when he arrived in Missouri. He paid $160 for eight acres of land in Saline County, Missouri, which was the start of what would ultimately be known as Pennytown. He then divided his land into small lots and sold them to other black settlers. By 1879, there were eleven land acquisitions from Black families that averaged 6.5 acres, which constituted the 64 acres known as Pennytown.
In 1886, a white landowner permitted Pennytown residents to erect a frame house of worship on his land. In 1894, church trustees purchased the land for $20. The building burned in 1924, but a new church was completed on the same spot by 1926.
As Pennytowners took up residence elsewhere in order to have better jobs and better education for their children, they also sought to establish a connection with the past. At the end of World War II, former Pennytowners organized an annual homecoming to be held on the first Sunday in August.
For nearly 50 years, homecoming has been held at the last building still owned by Pennytowners – the First Freewill Baptist Church. Each year, Pennytowners and their descendants gather there to sing long-remembered spirituals and illuminate the past for younger generations. Over the years, the little church grew frail; it lost its windows to vandalism, its roof to the elements, and it began to collapse.
In August 1996, as they had been doing for 50 years, Pennytowners from throughout the United States came back to the church for the Pennytown homecoming. During this time, more than 200 people gathered on the lawn to greet old friends, eat dinner and have service.