3.4 km
Middle Head
1870s gun emplacements cut into the cliff, looking straight out through the heads to the open ocean.
-33.8270, 151.2676Sydney, Australia
Harbour bushland, hidden beaches and the best skyline view in Sydney
Ten kilometres from Balmoral Beach out to Middle Head, down to Chowder Bay and Clifton Gardens, then along the foreshore track to Bradleys Head and the Taronga Zoo wharf. Bush singletrack, harbour beaches, gun emplacements and a skyline view that stops you dead.
Route map
Route timeline
0 km
Start on the esplanade and climb toward Middle Head Road.
3.4 km
Out to the fortifications and the harbour-mouth lookouts.
5 km
Back west along the clifftop with the city ahead.
6 km
Down to the wharf, cafes and the beach.
6.8 km
Netted swimming, taps and toilets.
8.8 km
The mast, the amphitheatre and the skyline.
10 km
Finish at the ferry — twelve minutes to Circular Quay.
Route highlights
3.4 km
1870s gun emplacements cut into the cliff, looking straight out through the heads to the open ocean.
-33.8270, 151.26766 km
Old naval buildings, a working wharf and a netted harbour beach with a jetty — the halfway swim stop.
-33.8390, 151.25458.8 km
The mast of HMAS Sydney on the point, and the Opera House, Harbour Bridge and city lined up across the water.
-33.8510, 151.2447Photo stops

Sandstone tunnels and cannon platforms hanging over the harbour entrance.

The cleanest skyline view in Sydney — bridge, Opera House and city in one frame.
Local knowledge
Safety
Mixed trail, steps and short road sections. Watch for cyclists and loose sandstone after rain.
2 water points · 2 toilet stops on route
Time the finish to the ferry timetable and ride back past the whole route from the water.
Route pack
The GPX file plus everything on this page, ready for your watch and your pocket.