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City · #11 of the Top 500

Sydney

New South Wales, Australia

Sydney is read from its edges: sandstone headlands, ferry wharves, ocean pools and a steel arch you can cross on foot for nothing. Almost everything people come here for sits on open public ground, and many of the places you stand carry Gadigal and Guringai names beside the English ones.

7 challenges · 38 stops

Harbour First Light crestSTARTER

Harbour First Light

≈ 2,500 steps1.2 mi · about 2 hoursStarter · 3 stops · 500 credStart where you live.

Two hours around the eastern edge of the harbour before the ferries get busy: the forecourt under the sails, the writers' plaques set into the Circular Quay promenade, and the sandstone point where the bridge and the shells line up.

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The Rocks on Gadigal Ground crestSTARTER

The Rocks on Gadigal Ground

≈ 1,700 steps0.8 mi · about 2 hoursStarter · 3 stops · 500 credStart where you live.

Two hours on foot through the oldest colonial streets in the country and the ground underneath them: the point beneath the bridge, a lane named for convict nurses, and the hill the harbour opens from.

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Across the Arch and Down the Other Side crestSTANDARD

Across the Arch and Down the Other Side

≈ 7,000 steps3.3 mi · about 4 hoursStandard · 5 stops · 600 credOne trip earns it.

Climb the stairs off Cumberland Street, cross the harbour on the bridge's eastern footway, then work the north shore foreshore west to a lawn that faces the whole thing. Half a day, best finished at sunset.

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The Clifftop Between Five Beaches crestSTANDARD

The Clifftop Between Five Beaches

≈ 7,000 steps3.3 mi · about 3.5 hoursStandard · 5 stops · 600 credOne trip earns it.

Six kilometres of public clifftop from Bondi to Coogee, past ocean pools, a whale-watching headland and a cemetery on the edge of the sea. Half a day at a walking pace, with swims in it.

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Western Harbour to the Food Street crestSTANDARD

Western Harbour to the Food Street

≈ 9,000 steps4.4 mi · about 4 hoursStandard · 5 stops · 600 credOne trip earns it.

The other side of the city, from a rebuilt sandstone headland along Cockle Bay to the Glebe foreshore, finishing on a terrace-lined street of small kitchens as the lights come on. Half a day, ending at dinner.

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Pittwater and the Far North Headlands crestADVANCED

Pittwater and the Far North Headlands

≈ 3,000 steps + 19 mi by car1.5 mi on foot · 1 day or more · + the walk in to 5 stops · + 1 stretch not routedAdvanced II · 9 stops · 800 credGetting there is not the hard part.

Two days and a car, north up the beaches from Freshwater to Palm Beach and then into Ku-ring-gai Chase: headlands, a lighthouse you walk up to, ochre hand stencils, and the estuary side of the same park. Park vehicle fees apply at West Head and Bobbin Head.

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The Spit to Manly and the Heads crestADVANCED

The Spit to Manly and the Heads

≈ 10,000 steps + 6.0 mi by car4.8 mi on foot · a full dayAdvanced · 8 stops · 800 credGetting there is not the hard part.

Ten kilometres of harbour bushland from the Spit Bridge to Manly, then the ocean side and the top of North Head. A full day on foot with a bus or a ferry at either end, and several swims if you want them.

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Counted between stops; you'll walk more at each one.

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