The original town well was dug by slaves on this site in 1860, and a saloon was built over it in 1891. The First National Bank acquired the property, filled in the well, and commissioned this building. Raif Stripling purchased the building several years later and reopened the well as a tourist attraction. In 2003, the San Augustine Historical Foundation bought the property, which is now operated as a gift shop. The entrance canopy’s curious pediment with miniature triglyphs was added to his father’s building by Raiford Stripling.
In the alley behind the 100 block of E. Columbia Street, facing N. Montgomery Street, stands the two-story brick jail of 1882, used for many years as Raiford Stripling’s office. Walls of local red brick are seventeen inches thick on the first floor and thirteen on the second, with Italianate shawl lintels over the segmental-arched windows and entrance. A brick frieze runs under the corbeled brick cornice and hipped roof.