[1] The Observer Hotel is built on the west side of George Street North on land which was, from 1788, part of the grounds of the prefabricated, temporary hospital.

Frederick Garling Jr., a noted maritime artist, painted a series of views of Sydney Harbour c. 1839, one of which included his family residence which had recently been sold.

Unwin subdivided the property into a series of lots and c. 1845 erected the substantial sandstone stores just south of the site that survive today.

[1] By 1810 there were 75 "licensed houses" in NSW, a number of which were located "on the Rocks", particularly fronting George Street North and in nearby Millers Point.

[1] The Observer Tavern, as it was originally known, was built in 1848 for Robert White Moore who had purchased Lot 10 of Frederick Unwin's subdivision the year before.

The Waterman's Arms reflects the numerous watermen who operated row boats on Sydney Harbour, the forerunner of the water taxi and the men may have gathered there waiting for a commission.

[1] The two-storey six roomed building constructed as the Observer Tavern for Moore was built of brick walls with timber floors and a shingle roof.

It was common practice in NSW to hold coronial inquests in public houses, although by law if there was a morgue or police station within one mile, it had to be used in preference.

[1] The Observer Tavern and the new Coroner's Court were both part of the extensive urban renewal in George Street North undertaken following the 1900 land resumptions.

The former Waterman's Arms was owned by the Union Bank of Australia, the Observer Tavern was the estate of Arthur Malcolm Moore.

A record plan was prepared in December 1901 which indicates that the Waterman's Arms was one of the many substandard buildings identified for demolition by the Resumed Properties Branch.

The demolition also allowed for the straightening and widening of Mill Lane, and the regularisation of the block fronting George Street North.

Weeping friends can wet eye and whistle while awaiting coronial pleasure.Plans for the new "Observer Tavern Hotel" prepared by Halligan and Wilton on behalf of Tooth and Co. brewery were submitted to the Sydney City Council in March 1908.

The ground floor included a bar, two parlours (one of which was for the residents), a dining room, pantry, kitchen, laundry, spirit store.

The dining room was also only accessible from the private entry and there was originally no connection into the public bar which fronted George Street North.

[1] In June 1920 Tooth's architect Mr. J. G. Dalzeil prepared a report noting that the following works to the site and building of the Observer Hotel were required: The hotel was described as: A three storey brick building of modern design and good appearance, containing on the second floor five bedrooms, and on the first floor three bedrooms, all of which are up to requirements, reasonably clean and sufficiently furnished.

On the ground floor there is a fairly large bar, good cellar, two parlours, private entrance, dining room, kitchen and laundry, whilst at the rear there is a storeroom, small stable, public lavatories and yard.

The publican wrote to Tooth & Co. informing them of the results of the inspection and that the Licensing Court required a second bathroom and that repairs to the exterior should be undertaken.

The wharves had been shifted to the east side of Circular Quay.Tooth's reduced Fyfe's rent twice and their files note that as he had been there since 1925 "it does not look like a case where we can charge him with incompetency".

[1] Tooths attempted to counter the impact of the Great Depression by appealing to a wider clientele, and the board room at the Kent Brewery still retained some of their art work from the 1930s depicting elegant women in evening wear.

Similar examples of the advertising for Tooth's KB Lager from the late 1930s are held in the Powerhouse Museum, including sportswomen.

Tooths had been aware for some months that the resumption was to take place and did not wish to fund the publican's request for the roofing of the beer garden.

Faced with the possibility of owning an unlicensed hotel building whose highest and best use was as a pub, the Authority decided in 1972/73 to purchase the licence for $75,000.

This investment decision was made because: Advice indicated that the Licence Reduction Board would not be interested in creating a new licence for The Rocks, to replace that of the Observer, The Authority had always been of the opinion that The Rocks needed more low cost (hotel style) accommodation and the potential for an amplified hotel redevelopment was obvious even then.

[1] In 1978 the Observer Hotel, the Kendall Lane precinct and the entire Rocks, as a conservation area, was listed on the (now defunct) Register of the National Estate.

In 2006 a historic mural painted on the rear wall of the hotel by artist Helen Davies received an Energy Australia National Trust Heritage Awards for Highly Commended Interpretation and Presentation.

It embodies a fragment of The Rocks social history by virtue of the need to protect patrons by incorporating internally supervised lavatories.

The substantial urban renewal of The Rocks and Millers Point would appear to be the most extensive scheme undertaken in Australia in its day.

The rebuilding of the hotels indicates that the impact of the Temperance movement, which sought to limit the number of liquor outlets in order to reduce alcohol consumption, had yet to be felt.

[1] The place is important in demonstrating aesthetic characteristics and/or a high degree of creative or technical achievement in New South Wales.