The Old Wentworth Gaol is the most well-known building in Wentworth. Built in 1879-81 it is a small single storey brick gaol with bluestone trim. It was the first of the Australian designed gaols, Hay & Dubbo gaols followed this one. It is a real testimony of the building skills of the day. It consists of 8 male cells, 2 female cells and 2 large cells for overnight drunkards. It served a large area yet only operated until 1927. The tour gives an insight into what a struggle life could be in colonial times. After its closure as a gaol the building was used as extra classrooms for the Wentworth Central School until 1963 and today due to its remarkable condition it is a major tourist attraction.

 It appears the architect erred badly when he only made 2 female cells. By all reports they were often overcrowded and in October 1898 for example 14 women were cramped into 2 small cells. Surprisingly perhaps by today's standards 7 of them were members of the Salvation Army. It appears the Salvo's were incarcerated regularly during the life of this gaol, not because of any criminal act but rather because they were seen to stand outside the orthodox religious order. The common pretext for gaoling was breaches of the street procession bylaws. In reality that meant that they had been singing songs of praise on a street corner, thereby upsetting the established religious. It was common for the Salvation Army women to receive 7 days detention for their transgressions and their male counterparts 14 days.