Based on visual evidence, the photograph likely dates to the early–mid 1920s, circa 1923–1926. The presence of open-top touring cars with narrow tires and upright bodies is consistent with Ford Model T-era vehicles, which remained common until 1927.…
The date of this photo is unknown, but one can estimate that it is after 1908, when the courthouse was built, and before 1914, when the Shingler Building was built since that is missing from the photograph.