Walking Tour: A Rock-Quay Road

  • Start Cadman's Cottage
  • End Royal Botanic Garden
  • Length 3.5km; two hours

Start outside Cadman's Cottage, inner-city Sydney's oldest house. It was built on a now-buried beach for John Cadman (a government boat superintendent and former convict) in 1816. Sydney Water Police also detained criminals here in the 1840s. It now sits slightly forlorn, little-used among the bustle of the surrounding area.

Head north along Circular Quay West past the Overseas Passenger Terminal, where multi-storey luxury cruise ships regularly dock. For a killer harbour view, if there's no ship to block it, head up to the level-four observation deck in the turret on the northern end.

Further along the quay are Campbell's Storehouses, which date from 1839 and were built by Scottish merchant Robert Campbell, a key early trader into the colony who became an eminent local figure. Construction didn't finish until 1861, and a brick storey was added in 1890. Such buildings were common around Circular Quay into the early 20th century, but most have been demolished since. These survivors now sustain a string of touristy restaurants in a recently refurbished precinct.

Play spot-the-bridal-party as you loop past the Park Hyatt and into the small park at the end of Dawes Point. Couples jet in from as far away as China and Korea to have their photos taken here in front of the perfect Opera House background.

As you pass under the Harbour Bridge, keep an eye out for Luna Park on the opposite shore. Stroll around Walsh Bay's gentrified Edwardian wharves and then cross the road and cut up the stairs (marked 'Public stairs to Windmill St') just before the Roslyn Packer Theatre. Continue up the hill on teensy Ferry Lane. Near the top you’ll find the foundations of Arthur Payne's House; he was the first victim of the 1900 bubonic plague outbreak.

At the corner of Windmill St is the Hero of Waterloo, a contender for the title of Sydney's oldest pub. Turn right on Lower Fort St and head to Argyle Place, a quiet, English-style village green lined with terraced houses.

Across the road is the handsome Garrison Church, the colony’s first military place of worship. Hook left into Argyle St and stroll down through the Argyle Cut. Convict labourers excavated this canyon-like section of road clear through the sandstone ridge that gave the Rocks its name. It was a major engineering feat of its day (the mid-19th century) that connected the eastern and western sides of the Rocks, bypassing the ridge (and, these days, the freeway approaching the Harbour Bridge).

In the Cut, take the stairs up to the left and head along Gloucester Walk to Foundation Park, which evokes the area's cramped past. Descend through the park, duck around the building at the bottom and exit onto Playfair St where there's a row of historic terraced houses.

Cross Argyle St into Harrington St then jag left into Suez Canal. The narrowest of these typical Rocks lanes (hence the name, also a pun on the word 'sewers'), it is fairly salubrious these days, but was once a rat- and effluent-ridden haunt of thieves and topers, most notably street gang the Rocks Push.

Turn right into George St and cut through the Museum of Contemporary Art, Sydney's major showcase for big-name exhibitions. Exit onto Circular Quay and follow the waterline past the ferry wharves.

Walk underneath the train station to the fabulously renovated Customs House. Stroll back to the water to check out the bad buskers and the metal plaques of the Sydney Writers Walk. Serious and comic observations by an eclectic assemblage of authors, including Mark Twain, Germaine Greer and Clive James, cover a wide spectrum of topics, ranging from impressions of the harbour by Joseph Conrad to hopes for racial harmony in Australia by Oodgeroo Noonuccal.

Continue past the Opera Quays apartment and entertainment complex on Circular Quay East, which is disparagingly referred to by Sydneysiders as ‘The Toaster’.

The heaven-sent sails of the Sydney Opera House are directly in front of you, adjacent to an unmissable perspective of the Sydney Harbour Bridge off to the left. Circumnavigate Bennelong Point, then follow the water’s edge through the gates of the Royal Botanic Garden.