This is Stop 11 on the Spit to Manly Walk as marked on the Manly to Spit Walk Map.

The first known non-Aboriginal person to see Sydney Harbour was Lieutenant (later Captain) Cook of the Royal Navy. In 1770 he noted in his log that he sailed “about 2 or 3 Miles from the Land, and abreast of a Bay, wherein the appear’d to provide safe Anchorage, which I called Port Jackson”. Although, some people believe Portuguese ships have been recorded in Aboriginal rock engravings along Australia’s east coast, pre-dating English exploration.

On January 21st, 1788 Captain Phillip of the Royal Navy set out from Botany Bay, 20km south of here in three long boats. They had found Botany Bay unsuitable for settlement, despite “Captain” Cook’s strong recommendation, and sailed north to explore Port Jackson and Broken Bay (Hawkesbury River). After rowing into a stiff nor’easter all morning, they reached the heads and set their sails. They sailed down Middle Harbour, on your right, towards the Spit on a gorgeous Sydney summer afternoon. This prompted Captain, soon to be Governor, Phillip to write in a letter home in July 1788 that Port Jackson was “without exception the finest Harbour in the World… where a Thousand Sail of the Line may ride in the most perfect Security.”

They returned around this headland to North Harbour, which Captain Phillip named Manly due to the “confident and manly behaviour” of the local Aboriginal people. Before dusk they sailed across the harbour entrance to the beach inside South Head, calling it Camp Cove, at present day Watsons Bay. Here they stayed the night, the first Europeans to call Sydney home.

Across the water on the shoreline of North Head is the old Quarantine Station. It was built in the 1830’s to try and prevent Smallpox, Spanish Flu and Bubonic Plague from entering the colony. The site was selected for its isolation from Camp Cove and it being the first safe anchorage inside the heads. It’s rich in early settler history and fascinating stories from people quarantined upon arrival to their new home. Closed in 1984, the heritage buildings now house Q Station luxury hotel and Boilerhouse Restaurant, and we highly recommend a visit.

Read more about the Spit to Manly Walk and download the Manly to Spit Walk Map. Jump to any stop by clicking on the name below.

Stop 1: Ellery’s Punt Reserve
Stop 2: Fisher Bay ‘Midden’
Stop 3: Fisher Bay Houseboat
Stop 4: Sandy Bay, Hawkesbury Sandstone
Stop 5: Clontarf Reserve
Stop 6: Clontarf Pumping Station
Stop 7: Castle Rock Beach
Stop 8: Grotto Point Lighthouse
Stop 9: Grotto Point Aboriginal Engraving Site
Stop 10: Crater Cove
Stop 11: Dobroyd Head – you are currently on this page
Stop 12: Reef Beach
Stop 13: Forty Baskets Beach
Stop 14: North Harbour Reserve
Stop 15: Fairlight House
Stop 16: Manly Wharf

Image courtesy of Hamilton Lund, Destination NSW


Ian Wells grew up in Sydney surrounded by Cronulla surf beaches, Port Hacking and Royal National Park, developing a love of the outdoors from an early age.

After nearly a decade travelling the world, he returned home to realise his own backyard was as extraordinary as the places he‘d seen.

With the advantage of local knowledge and a belief that the best natural beauty can only be experienced by foot, he founded Sydney Coast Walks in 2009.

Sydney Coast Walks also provides supervised hikes for the Duke of Ed Award. Coming soon, Ian will co-host new podcast This Hiking Life with his wife Tara Wells.

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