Bailey Head has been the civic centre of Oswestry since the late thirteenth century when John Fitzalan, Lord of Arundel granted the burgesses of Oswestry 'free power and authority to ordain make and pass amongst themselves laudable ordinances and agreements...' In the 1530s, John Leland visited Oswestry and recorded that there was a town hall situated next to the castle. The Guildhall has been at its present location since c. 1839 when Powis Hall (the former centre of civic functions) became one of the town's new markets.
The old Guildhall was enlarged in 1877, but by 1890, it was considered unsound by the town's surveyor. The Council decided to build a new municipal building. The old Guildhall was demolished in 1892.
The new Guildhall was designed by Henry Cheers of Twickenham in the style known as 'seventeenth century renaissance freely treated'. The building was built by W. H. Thomas of Oswestry and opened in November 1893. It cost the Corporation about £11000. The new Guildhall not only provided offices for the Council and the town surveyor, it also housed the County Court and a library.
By the 1990s the Guildhall was again in need of major repairs. The building required reroofing and there was evidence of dry rot. The Town Council submitted a bid to the Heritage Lottery Fund in 1995. The bid was successful receiving £225,300 towards the total cost of £300,400 to:
- Resolve dry rot problems
- Provide internal and external disable access (including a four-storey lift) to the Attfield Theatre and Municipal rooms
- Create a home for the Oswestry Parish Maps in the foyer area (the wonderful decorated panels created by the Lorne Street Day Care Centre Group, depicting the history, topography and people of Oswestry
- Improving access to and security for the local records held in the Town Council Archive. This would enable the Guildhall to maintain its status as a place of deposit under the Public Records Act 1958.
The refurbishment was not without its troubles. The dry rot problem escalated, but the Heritage Lottery Fund increased their funding to £326,300 to help with the total costs of £435,066.
The Guildhall was formally reopened by the Lord Lieutenant of Shropshire Algernon Heber Percy J.P. in April 2000.
In 200X the County Court moved out of the building. It was replaced by the town's new Museum in 2012.