Old George Street – A Chapter in Old Sydney

This website explores the oldest road in Australia, George Street. The content is from a frail old book The Story of Old George Street – A Chapter in Old Sydney by Charles H. Bertie. The book includes the history, the landmarks and buildings plus all the crazy characters that made this Sydney street unique.

‘It has been said that the streets of Sydney were laid out by the bullock waggons of the early settlers. This is not correct as in the first place there were no bullock waggons in the First Fleet, and such was the primeval condition of the shores of Sydney Cove then that, even if there had been waggons, the contour of the ground itself prescribed where the main roads must run.’


The arrival of the first fleet

Clearing A Path For Old George Street

Oldest Road in Australia


Slaughter House -The Slaughter house was located close to the present Dawes Point Wharf, Sydney.

Dawes Point – Lieutenant Dawes erected his observatory in 1788, and the point was called “Maskelyne” in honour of the Astronomer-Royal, but a later changed in honor of the officer.

Bethel Street – A headstone of a man from the First Fleet named George Graves was used in Bethel Street to fill in a crack in the pavement

The Sailor’s Home

Cadman’s Cottage – Cadman’s Cottage was built in 1816 and was originally known as Coxswain’s barracks. It is Sydney’s oldest surviving house.

Argyle Street – For many years this area on Argyle Street was the dockyard of Sydney.

First Sydney Hospital – The first hospital in Sydney and indeed Australia was located on Old George Street

Australia’s First Post office – Australia’s first post office was established by Isaac Nichols

The Commissariat Stores – The Commissariat Stores (now Argyle Stores) were eventually owned by Mary Reibey Sydney’s first woman merchant

Mr Wills House – George Howe started the first Australian newspaper, the “Sydney Gazette,” in 1803 and moved the establishment to George Street when he married Mrs Sarah Wills

Old Sydney Gaol – The gaol was once a prominent feature in this part of George street

Essex Street – Essex Street was once the location of the Bank of Australia

Grosvenor Street – The fine mansion of Lieutenant Kent which was later turned into an orphanage.

Sydney Hotel – The Sydney Hotel, was located on the southern corner of George and Grosvenor Streets.

Jamison Street – The street was named in honour of Sir John Jamison

Barrack Street – Governor Macquarie’s fondness for stone walls resulted in Barrack Street being walled.

Bridge Street – On Bridge Street was the Lumber Yard, where the convicts in the Hyde Park Barracks were employed.

Wynward Street – When the barrack square was cut up a new street was opened to York street, and called Wynward street after the commandant of the forces of the day

Bond Street – Bond StreeI was to be the location of the first bazaar in Australia

Hunter Street – Hunter Street in Sydney was once the home of the Bank of New South Wales

Martin Place – The Post Office in Martin Place was the first in the world to use a stamp

King Street – In the 1800s the street was home to Black Boy hotel, Boxing Saloon, White Horse Tavern and the MacDonald’s Building.

Market Street – In the 1800s the street was home to Kidman’s Grocery Store, the New Order and the Waterloo Warehouse

Market Square – “Market-square,” and was thrown open on October 25, 1810.

Town Hall –  Town Hall and the coffin

St Andrew’s Cathedral – Macquarie conceived the idea that Sydney required a Cathedral Church

George Street South – In the 1800s the street was home to Bob Cooper’s inn, a Scottish Watchmaker, Bookstalls and Anthony Hordern and Sons.

Toll House – The toll house was designed by Francis Greenaway and was the most ornate toll bar that Australia ever possessed.

Haymarket -The old Haymarket building was erected in 1834. It was a red brick building resting on arches and fronted George street.


Grosvenor Street Duel – Lieutenant Marshall Goes Mad

Billy Bluemuch-loved street performer

Captain Piper Causes a Financial Crash

Stocks and Pillories – The first stocks were located in the old gaol in George Street North.

Robert Campbell – Robert Campbell fought to open up an export trade with England but came in conflict with the East India Company’s monopoly.

John Baughan – In the early part of 1796 Baughan occupied the position of foreman carpenter, and one day had a dispute with a soldier of the N.S.W. Corps