It was the first of the early Sydney suburbs that was not self-sufficient – its inhabitants, unlike those of Balmain or Newtown, where work was available in local industries, had to go away each day to their places of employment.

John Palmer, the settlement's commissary, refused to allow people to cross his land grant ('Woolloomooloo'), so the road had to follow a roundabout way through Paddington to bypass his 40 hectares (100 acres).

[2] From 1848 when Victoria Barracks had been opened (designed by Lt.-Col. George Barney) and homes for the soldiers and their families had been erected, Paddington began to assume a real identity...The (barracks site) land was sandy - in fact a huge sandhill was located on the western side of the Greens Road area, and the foundation trenches had to be dug very deep, to locate firm stone for the foundations.

[2] It is hard to imagine that in 1822 the mansion Juniper Hall (the opposite southern corner of Oxford Street from the Reservoir site) stood alone, without the many neighbours it has today.

Juniper Hall was built for Robert Cooper, distiller and emancipist merchant, who with partners James Underwood and Francis Ewen Forbes, had received 40 hectares (100 acres) from Governor Brisbane in c. 1818, covering the whole of north Paddington, and they agreed to erect three mansions and a distillery there.

A distillery was built at the foot of Cascade Street near Taylor Square and Cooper bought out his partners, and only Juniper Hall was erected.

The bazaar, which has operated since the mid-1970s, draws visitors from all over the city and has contributed to Paddington's development as one of Sydney's favourite tourist spots, along with Bondi Beach and The Rocks.

The first three meetings were held in the Paddington Inn before Council resolved to rent Mr. Logan's house next door for 12 months at 15 shillings a week.

Meetings continued to be held at the house until the first Town Hall was built on the current site of the Royal Women's Hospital in Oxford Street in 1866.

[2] Situated at the highest point on the Oxford Street ridge, the town hall's foundation stone was laid on 8 November 1890 by Sir Henry Parkes and was opened with great fanfare on 3 October 1891 by the Governor, The Earl of Jersey.

[2][4][5] The first major alteration to the Town Hall occurred in 1904–1905, when the clock tower was erected in commemoration of the coronation of King Edward VII.

On 10 September 1969, the congress of the Australian Council of Trade Unions (ACTU) was held at the town hall, with Bob Hawke being elected as the new president.

[2] The City of Sydney, the Australia Council and the Australian Film Commission provided $500,000 to redevelop the Town Hall as a centre that included an exhibition space, restaurant and an adjacent cinema.

[9] The principle decorative elements are "an open colonnade to Oxford Street and rows of Roman-arched first-floor windows flanked by Corinthian pilasters and a balustered parapet".

[2] The Town Hall has a 32-metre (105 ft) high clock tower, completed in 1905 to commemorate the coronation of Edward VII, that dominates the Paddington skyline.

Whilst the eastern, southern, and western faces of the clock display the conventional Roman clock-face numerals, the Roman numerals on the northern (Oxford Street) side of the clock have been replaced as follows: 1:D, 2:U, 3:S, 4:T, 5:H, 6:E, 7:VII, 8:E, 9:D, 10:V, 11:A, 12:R. This was done to celebrate the coronation of King Edward VII; and, commencing at where the VIII ought to be, the northern clock-face reads E.D.V.A.R.D.U.S.

[13] The main vestibule can be entered from both Oxford Street and Oatley Road and the internal decoration continues to utilise ornamented archways to harmonise with the exterior.

The coffered ceiling was retained, but much of the original plasterwork has been removed - replaced with open grille work matching those cut in the wall.

The Town Hall's construction in 1891 marked the beginning of the 1890s depression as is historically significant as one of the last public buildings to be built in the style.

[2] Paddington Town Hall was listed on the New South Wales State Heritage Register on 2 April 1999 having satisfied the following criteria.

The Paddington Town Hall is of State significance as one of the last Victorian Free Classical public buildings and as such it exemplifies the architectural style.

The Paddington Town Hall is of local significance as the focus of community activity in the area through the location of library and other services in the building.