Sydney Culture Trails: The Rocks & Surrounds

Sydney Culture Trails:

The Rocks & surrounds

Step back in time as you amble through some of Sydney’s oldest buildings and renewed precincts that pay homage to the city’s harbourside past on the Rocks and surrounds cultural trail.


Customs House

(Map Point A)

Free entry

Arrive at Circular Quay via tram, train or bus and walk to Customs House. Standing on Gadigal land, the Customs House opened in 1845 and was once an icon of British rule. While the landscape around the building has changed from mangrove swamps to colonial offices to shiny skyscrapers, the House itself has remained and is one of the city’s oldest surviving architectural gems. Explore a scaled-down model of Sydney underfoot, discover exhibitions, and enjoy a meal in the historic building.

Customs House at night

Fuel stop:

Head to the rooftop to dine at the iconic Cafe Sydney with dazzling postcard views of Circular Quay and across Sydney Harbour.


Museum of Contemporary Art - MCA

(Map Point B)

Free entry

A celebration of today’s artists, the Museum of Contemporary Art is a significant institute of creativity in Sydney and, indeed, Australia. The handsome Art Deco-inspired building once housed the Maritime Services Board but is now a cutting-edge gallery complete with a modern, five-storey wing, added in 2012. Ever a thought-provoking and incredible experience, be sure to dedicate time on your itinerary to thoroughly delve into the collection.

Fuel stop:

Enjoy an elegant post-art lunch as you watch the ferries dock at Circular Quay at the MCA cafe and sculpture terrace. Or if you’re looking for a more casual option, grab a rock-n-roll-style burger at Mary’s Circular Quay.



The Rocks Discovery Museum

(Map Point C)

Free entry

Step inside this 1850s-era sandstone warehouse and be transported back in time. Beginning with the First Nations people of Warrane (the Gadigal name for Sydney Cove), who predated the arrival of the British by many thousands of years, you’ll then journey through to colonial times and onto landmark events that led Sydney to its current period of prosperity. Essentially Sydney’s old town, be sure to have a wander through the historic streets of The Rocks before continuing on your trail.

The Rocks Discovery Museum. Image Credit: Place Management NSW

The Rocks Discovery Museum. Image Credit: Place Management NSW

Fuel stop:

While you’re strolling through The Rocks, make a note of some of the nearby fine dining options to return to come nightfall, such as the impeccable Quay (best to pre-book) or Sake Restaurant for contemporary Japanese.



Pylon Lookout and Museum

(Map Point D)

Admission fee applies

Housed in the south-east pylon of the famous Harbour Bridge is a museum that offers incredible views of the harbour and guides you through the building and creation of one of Sydney’s most iconic structures. It may not be on your agenda today but consider booking a climb to the 134-metre summit of the bridge. While you’re in the vicinity, amble across to the adjacent Dawes Point Battery remains to marvel at the 1791-built military installation.

Sydney Harbour Bridge Pylon Museum and Lookout

Sydney Harbour Bridge Pylon Museum and Lookout. Image Credit: BridgeClimb Sydney


Sydney Theatre Walk

(Map Point E)

Honouring 21 idols of the stage and screen who have contributed to Sydney’s theatrical history, this short meander at the Walsh Bay Arts Precinct glitters as much as the adjacent water. Occupying historic wharves, the precinct is the home to the city’s most world-renowned and accomplished performance ensembles, including the Sydney Theatre Company, Bangarra Dance Theatre, and Sydney Dance Company. Watching a performance here should be on your Sydney to-do list, so be sure to book ahead and make a night of it with a stay at the nearby Pier One hotel.



(Map Point F)

Free entry

One of Sydney’s most recent and ambitious renewal projects, Barangaroo belies very little of its former industrial life as a container terminal. Weaving along the water’s edge, the precinct brims with incredible eateries, parklands, exciting shopping, cultural experiences, and the six-star Crown hotel. Coming from Walsh Bay, begin your exploration by dipping into Barangaroo Reserve. This large landscaped green space provides beautiful vantage points, lovely lawns, and the purpose-built Cutaway event space. Not to be missed is the important audio-visual artwork Wellama, which welcomes visitors to Gadigal country, and the multimedia Indigenous experience Ngangamay, embedded in the sandstone and accessed via a downloadable app, that honours Barangaroo, the powerful Aboriginal woman after whom the precinct is named.

Fuel stop:

Barangaroo is a culinary hub taking full advantage of Sydney’s stunning weather and harbour views. From Asian-fusion brunch at Devon Cafe, to elegant Chinese dumpling restaurant Lotus and Bea at the flagship Barangaroo House, you could easily graze from breakfast through to a night cap here.

Barangaroo House

Barangaroo House, Barangaroo


Sydney Observatory

(Map Point G)

Admission fee applies

Walk from Barangaroo Reserve over the Sydney Harbour Bridge to Milsons Point to view Sydney Observatory. This scientifically and architecturally compelling site was built in 1858 and while its gaze is affixed to the night sky, it also offers some of Sydney’s most attention-seeking views. The Observatory hosts astronomy workshops and talks, but you’re also welcome to come and marvel at the beauty of the building.

Sydney Observatory. Image Credit: Marinco Kojdanovski

Sydney Observatory. Image Credit: Marinco Kojdanovski

Fuel stop:

This corner of Sydney is well-supplied with historic public houses, two of which are nearby to Barangaroo. The Hotel Palisade offers refreshments from its lofty position at Millers Point, while The Lord Nelson Brewery Hotel has been pouring pints since 1841 in The Rocks.

Hotel Palisade

Inside Henry Deane at Hotel Palisade 

Things to do & places to stay