Customs House was where shipping was cleared and goods passing through the port of Sydney were taxed for sale or export. When the port was busy the House was crowded and noisy, a scene of raised tempers, delays and disputed dealings.

The six-storey colonnaded building you see today evolved through several phases of expansion between 1845 and 1917.

On Loftus Street alongside the House, a Union Jack flies permanently on the site where the first British flag was raised. For some Australians, this is the site of invasion. Look up to see the Aboriginal flag flying from the roof of Customs House.

Originally swampy mangrove land on the banks of the Tank Stream, this triangular morsel of land is awash with historic relics.

The Obelisk records the distance in miles by road to important places in the colony and beyond. This sandstone monument was designed by Francis Greenway, who was sent to the colony for forgery and became Sydney’s first Colonial Architect.

Along one side of the park rest the cannon and the weathered anchor of HMS Sirius, flagship of the First Fleet which arrived in Sydney in 1788.

The imposing statue of 19th century industrialist Thomas Sutcliffe Mort looks out over Bridge Street, the colony’s premier financial street.

Bridge Street was named in 1810 for the wooden footbridge crossing the Tank Stream, the colony’s first water supply.

From the start, the town was both physically and socially divided by the Tank Stream. On the eastern side were the Governor’s house and the tents of the civil establishment. To the west were the makeshift barracks of the military and the convicts. Many signs of this social division remain today.

Along the high eastern section of Bridge Street, you will notice several impressive early government buildings, including the Lands Department, the Education Department and the Chief Secretary’s Building. The western end is more commercial, heading towards the once-raffish Rocks.

Sydney’s first Government House was built in 1789 for Governor Arthur Phillip.

In November 1789, two Aboriginal men, Bennelong and Colebee, were captured at Manly under Phillip’s orders and were held at Government House. After they escaped, Bennelong maintained cordial ties with Phillip. He often dined at Government House with his wife Barangaroo, and a number of Aboriginal people were buried within the gardens at his behest.

In 1995 the Museum of Sydney opened on the site. A forest of pillars made of timber, stone and steel stands adjacent to the museum entrance. This installation by Janet Laurence and Fiona Foley, Edge of the Trees, symbolises the interaction between Aboriginal and non-Aboriginal people at this important site of early contact.

Walk down Bridge Street to George Street. Notice the Australian Stock Exchange on the right and on the left, the impressive Burns Philp building. This was the headquarters of a powerful Australian mercantile company which shipped cargo and passengers throughout the South Pacific from the 1880s to the 1960s.

The redbrick Johnson’s Building and Brooklyn Hotel were designed by Walter Liberty Vernon and built in 1912. The Commercial Building in between them was constructed a couple of years later by the NSW Government as office space.

Grosvenor Place towers behind these old buildings, known collectively as Johnson’s Corner, after long-term tenant James Johnson, whose outfitting, tent making and drapery business remained on the site until 1981. A condition for erecting the Grosvenor Place tower, designed by Harry Seidler and built in the mid-1980s, was that Johnson’s Corner be retained.

Walk up Grosvenor Street to Lang Park.

In the 19th century, several churches clustered on the hill where Lang Park sits today.

St Philip’s Anglican Church was the first, built in 1798 after convicts burnt down the colony’s very first church near Sydney Cove. The current St Philip’s on York Street dates from 1848.

To the south, the Scots Presbyterian Church opened in 1826 but was demolished in 1926 to make way for the approaches to the Sydney Harbour Bridge. Its replacement was built in 1929, and converted to apartments in 2005.

To the north, St Patrick’s was built in the 1840s on land donated by William Davis, a convict who had taken part in the Irish Rebellion in 1798. St Patrick’s was Sydney’s second Catholic church. Its parishioners came from the colony’s boisterous Irish working class. Today, St Patrick’s is the oldest remaining Catholic church in Sydney.

Walk along Gloucester Street to the end then take the stairs down to Harrington Street. Under the overpass, check out the heritage murals based on photographs of The Rocks taken between 1901 and 1914. Take the old worn steps on your left up to Cumberland Place (7) and Susannah Place (8).

Early maps show a lane on the alignment of the Cumberland Place steps as early as 1807. They lead into Gloucester Street. You are now in a network of streets and laneways that form the heartland of old residential Sydney.

The little houses and the corner shop at 58–64 Gloucester Street date from the 1840s. They are now a museum where authentic interiors, including outhouses and basement kitchens, allow you to imagine typical mid-19th century working class life.

Directly opposite Susannah Place is the site of an archaeological excavation which started in 1994 and came to be known as the “Big Dig”. It revealed the foundations of over 40 houses, shops and hotels, all crammed onto this small site.

Some of the excavated remains are exposed and able to be viewed from the Sydney Harbour YHA.

You can learn more about the people who lived here at The Big Dig Archaeology Education Centre.

This is a typical early 20th century hotel, built in 1914. It retains its original pressed metal ceilings and etched glass fittings.

The split level bar follows the rugged lie of the land. The odd shape of the land is a result of street re-alignments for the building of the Sydney Harbour Bridge.

A short distance along Cumberland Street, on the other side of the basketball courts, take the pedestrian “Subway to Fort St” under the Sydney Harbour Bridge stairs. The hill in front of you is Observatory Hill Park (11).

This is the site of Sydney’s first windmill. Also known as Fort Phillip and Flagstaff Hill, it eventually became known as Observatory Hill after the building of the sandstone observatory in 1858.

While the colony’s astronomers were making scientific observations from this building, local Sydneysiders knew it best for its timekeeping. Every day at 1pm the ball on top of the tower dropped, and a cannon blast fired to signal the correct time. This was especially useful for ships in port, enabling the accurate adjustment and calibration of marine chronometers.

Around the hill from the Observatory is the National Trust Centre (12).

The oldest building in this complex is the two-storey former 1815 military hospital, now facing the expressway. This later became the famous Fort Street School, the first school to provide for teacher training in the colony.

Today, the National Trust Centre includes the S H Ervin Gallery, cafe and shop.

The second half of this walk will take you through a precinct where old 19th century sandstone buildings live side-by-side with red brick structures created in the first decades of the 20th century by the Sydney Harbour Trust. Thousands of men were employed cutting a deep swathe through the sandstone to create a two-tiered roadway system serving the new Walsh Bay wharves.

The Trust then in-filled the new landscape with utilitarian brick houses, shops and pubs. After that, building practically halted.

The small-scale village atmosphere of Millers Point is a surprise find for many visitors fresh from the towering commercial buildings of the surrounding city.

Take the Agar Steps down to Kent Street. Opposite the Agar Steps along High Street are early 20th century houses built by the Sydney Harbour Trust. Turn right and head down Kent Street to Argyle Street. Just before the corner, on your right, is the little St Brigid’s Church School, Australia’s oldest Roman Catholic building, constructed 1834–35. Diagonally opposite is the Lord Nelson Hotel (13).

Built in 1836 by former plasterer William Wells as his home, the Lord Nelson obtained its liquor licence in 1841, one year before the town of Sydney was proclaimed a city. This makes it one of the oldest pubs in Sydney.

Walk along Argyle Street past the village green to the Garrison Church (14).

This was the first official military church in NSW and serviced the military garrison at Dawes Point. Imagine the spectacle of the redcoats marching up Lower Fort Street from the artillery barracks to attend morning prayer. Although the church was officially called the Holy Trinity Church, it continues to be known as the Garrison Church. Military flags still adorn the church’s interior.

Look along Argyle Street to see the Argyle Cut (15).

The Argyle Cut is a striking example of convict public works. It was a colonial effort to overcome a challenging landscape, providing a more level crossing between The Rocks and Millers Point. In 1843, convict labour was deployed to cut the roadway through the rocky peninsula. It was completed in 1859 with the use of explosives and council labour. Bridges over the cut were completed later.

The Argyle Cut was altered again in the 1920s with the construction of the approaches to the Sydney Harbour Bridge.

Walk down Lower Fort Street to the Hero of Waterloo (16) on the corner of Windmill Street.

The rough-cut sandstone walls and heavy timber beams of the interior of the Hero of Waterloo evoke an atmosphere of the rough mariner’s life. This hotel was built by George Paton, a stonemason, in 1843. The Hero of Waterloo is the source of many local stories of concealed trapdoors, shanghaied sailors and rum smuggling.

Cross Windmill Street to Ferry Lane (17).

This flagstone laneway once led to the waterfront. The history of the area is told in the plaques and signs in the lane and in the reserve below, called The Paddock.

Continue down to Pottinger Street. A footbridge from Pottinger Street takes you to the upper level of Wharves 6/7.

These huge two-storey timber wharves were part of a massive reconstruction by the Sydney Harbour Trust, set up by the government in 1901 to modernise Sydney’s chaotic and inefficient waterfront. The wharves were intended to be built using concrete, but due to shortages of materials after World War I, timber was used. The wharves and their associated shore sheds form a rare group of industrial structures, built over a number of years from 1910.

New shipping technology in the 1970s rendered them redundant. But the finger wharves were gradually refurbished and repurposed, achieving a high standard in adaptive re-use. Today, the wharves house a vibrant residential, restaurant and cultural hub.

Retrace your steps to The Paddock, then take the path leading off Ferry Lane that runs along the rear of the houses on Lower Fort Street. At the end of the lane, take the steps up to Lower Fort Street. Next to you is Clyde Bank, a fine Georgian house which dates to 1824. Opposite is the Harbour View Hotel, built in 1924. Head along Lower Fort Street to Dawes Point/Tar-Ra (19).

Several geographical features in Port Jackson have dual names, including Sydney Cove / Warrane, Bennelong Point / Dubbagullee and Dawes Point / Tar-Ra. Here, the Geographical Names Board of NSW has officially recognised the original place names by pairing them with existing European names.

Tar-Ra is the name Aboriginal people gave the headland which now supports the southern pylon of the Sydney Harbour Bridge. The colonists named the point after the First Fleet astronomer who established an observatory and set up camp here. Lieutenant William Dawes was also a linguist. His friendship with the young local woman Patyegarang has resulted in one of the earliest dictionaries of Aboriginal words.

Dawes Point Park has archaeological excavations and interpretation relating to the early fortification built here to deter England’s international enemies. This is an excellent vantage point for appreciating the might of the Sydney Harbour Bridge, carrying its heavy cargo of trains and traffic overhead.

Make your way back to George Street passing the cast iron urinal (20).

This is the last remaining cast iron urinal in the city. Public conveniences and urinals (or pissoirs) were common streetscape elements in early 20th century Sydney.

Continue down George Street. You are now returning to The Rocks.

The higgledy-piggledy streets and narrow laneways which still define The Rocks record the first places the convicts and exconvicts made their own.

The vision of the convicts living in barracks weighed down by ball-and-chain is overstated. Many more convicts simply worked for the government during the day and worked for themselves the rest of the time, building houses, opening shops, running pubs and creating a new life.

Today The Rocks is a living museum and practically every place has a story to tell.

Make your way via Mill Lane or Argyle Street to Kendall Lane where you will find opportunities for further exploration at the Rocks Discovery Museum (21). Your walk ends here.