A jail was built in 1861 on Willow Street near due east of this alley opening. Inmates were escorted on foot by deputies from the jail to the courthouse for court hearings. Attorneys walked from their offices on the square to the jail to confer with their incarcerated clients. Although the jail ceased to exist on Willow in 1997, this alley has continued to be referred to as jail alley due to over one hundred years of this type use.

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Jail from where inmates were escorted through Jail Alley when jail was on Willow Street. The building later became Robertson County's 1° hospital in 1937. The building was demolished and the location is now the home of the Robertson County Archives.