In part two of Ian Dodd’s historical tours around Sydney, he takes readers to the north shore, exploring Mosman, Manly and beyond. Images by Chloe Cann

HOW: Drive
START POINT: Sydney Road, Opposite Manly Oval
END POINT: Buena Vista Hotel, Corner, Middle Head and Bradleys Head Roads, Mosman. Ph: 9969 7022.
Stand on the footpath of Sydney Road, Manly, next to the oval and parklands – and look to the other side of the street. At first it’ll look pretty boring; some 1960s units perched high on a cliff. But it was on this site that once stood a grand castle, it was a huge complex that had a bigger visual impact on Manly, than what St Patricks does today. (St Patricks is off Darley Road adjacent to Sydney Harbour National Park).
If you take a closer look at the cliff, you can still see remnants of that castle. A fine stone wall – and gargoyles keeping watch. There are even remnants of a terrace balcony. These are the ruins of Dalley’s Castle, or as it was officially known, Marinella.
It was built in 1884 by William Dalley, in the style of a Gothic revival castle and was given a Scottish name that means “home by the sea”.
William Dalley (1833-1888) was a parliamentarian and at one point acting Premier of New South Wales. Dalley was the son of convicts but that didn’t stop him. He became a lawyer and a satirist, before entering parliament. By all accounts Dalley was totally eccentric, but greatly respected.
After his early death, it seems noone really knew what to do with the building. It was turned into a boarding home, a school (known by children as the “haunted house”) and even left derelict for several years.
Despite a huge controversy, the landmark was demolished in 1939. Today, just the sandstone footings and those gargoyles protect what was once Manly’s most iconic home.
Next stop is in Mosman, at the intersection of Mosman Street and Badham Avenue. Walk a few metres along Badham Avenue and just before a sharp curve you’ll see a flag pole and chains in the rock face.
They’re remnants from the Mosman whaling station. That’s right, Mosman’s early years were characterised by a whaling station. And up here, way above the station was the perfect place to locate a signals point, to let ships know in the main harbour, when the bay was clear.
The station began in 1831 when Archibald Mosman and John Bell bought land to establish the facility. It prospered and in 1838, Mosman sold out to move to Glen Innes. He picked his time well, because within a decade the whaling industry had declined to such an extent, the facility was turned into a ship repairs yard.
A store still exists from that old station. It’s an impressive stone structure near the end of Avenue Road in Mosman Bay. For the past century, it has been home to the local Water Scouts – who still today have a whale as part of their logo.
Next, drive to Whiting Street and follow it down to the water of Sirius Cove. There’s a walking track down to the water and once there, turn left. A couple hundred yards further along, you’ll arrive at the Curlew Camp Interpretation Centre. 
This is where artists would once camp and explore the new genres in painting – such as impressionism. During the 1890s, this site attracted well known artists including Arthur Streeton and Tom Roberts. The area has changed little and you can really get a feel of what it might have been like in those years leading up to Federation. And if that’s not enough, the harbour views are stunning.
Return to the car and drive to Suakin Drive, Georges Head. This is a road that runs beside Georges Heights Oval and leads down to the Georges Heights Battery.
It’s an impressive stone structure built in 1871 to defend Sydney Harbour. Now abandoned, it is maintained by the Sydney Harbour Foreshore Trust and is still relatively in tact.
The fort was deemed necessary after the British Military pulled out of Australia in 1870. With so much money coming into the colony from the Bathurst gold rush, the Brits told us we were on our own and could afford our own defence – thus we built the fortifications to secure the colony. 
This fortification had four, 80-pound guns and two 68-pounders. It took three months for 250 soldiers to roll them there from a delivery point in North Sydney. 
Georges Head continued to have a military presence until 2002, because of its strategic position overlooking the entrance to Sydney Harbour.
Finally, time for a drink.
My choice, the Buena Vista Hotel, 76 Middle Head Road Mosman (ph: 9969 7022).
The pub dates back to 1901 and is a landmark in the area. It has been spruced up, but still retains its traditional pub feel, with an open fireplace and beer lounge.