Nominations for candidates for the office of councillor of the new Woollahra Council were called on 21 May 1860 and voting took place on 28 May at four locations:
On the day 154 people cast their votes – 46 at Double Bay, 59 at Upper Paddington, 9 at Watsons Bay and 40 at Sydney – electing nine councillors to represent the municipality.
The road to South Head, c1894. Leftwych’s Hotel, situated opposite the Signal Station, had ceased operations just before this photograph was taken.
The first meeting of the Council of the Woollahra Municipality was held in the offices of Messrs Rowley, Holdsworth and Garrick, solicitors, Elizabeth Street on 6 June 1860. In attendance were seven of the nine councillors including:
Richard Holdsworth, one of the original councillors and chairman of Woollahra Council in 1862. Holdsworth was a solicitor of the firm where the first meeting of Council took place.