The Riley House has its own story to tell about the community around it. During the late nineteenth and early twentieth centuries, the area just east of downtown Tallahassee and west of Myers Park Drive was an African American community called Smokey Hollow. According to the Tallahassee City Directory, published in 1904, there were five houses on Riley’s block on Jefferson Street, all owned by black men. In 1919, there were six homeowners and they too were black. Several other homes, owned or rented by blacks, surrounded the Riley property, extending up College and Gadsden Streets. This situation changed in the 1950′s, when plans for the Department of Transportation Building and the expansion of Apalachee Parkway encroached into the boundaries of the Smokey Hollow community. By 1978, only two houses remained, that of John Riley and John Hicks, a black tailor who lived across the street from Riley. Hicks died in the early 1970′s and his home was purchased by Colmar Corporation for speculative purposes.

In 1978, through the efforts of local preservationists, the Riley House became the second house in Florida, owned by an African American, to be placed on the National Register of Historic Places, the first belonging to Mary McLeod Bethune, whose historic home is located in Volusia County. In 1996, a group of Tallahassee citizens established a museum at the Riley House dedicated to African-American history and culture. This facility draws more visitors and tourist into the area while providing a historically diverse attraction.