10 underrated Sydney highlights most visitors miss

Beyond the beach and ferry terminal, Manly's true and massively underrated treasure is the North Head. Bandicoots and kookaburras flit around the national parkland, while the buildings of the former quarantine station are tucked into the clefts. The tours around what's now branded as the Q Station are riveting, telling the tales of many immigrants to Australia over the decades, and the treatment they got upon arrival. The mass shower blocks they'd be marched through and the fairly basic hospital wards they'd be kept in indicate it wasn't exactly a red carpet. See qstation.com.au

The Pylon Lookout

The entirely decorative stone pylons of the Sydney Harbour Bridge may as well have some use, and the one in the south-eastern corner can be climbed. You may swear at every one of the 200 steps on the way up, but the views from the top are pretty special. Think of it as the Bridgeclimb on a budget – you're 87 metres up – and there are exhibitions on the history and engineering of the bridge on the way. See pylonlookout.com.au

Macquarie Place

This easily overlooked triangle of land near Circular Quay is a treasure trove of oddities. First up is the Obelisk, constructed in 1818 with distances to key points such as Bathurst, Liverpool, Windsor and Parramatta engraved on it. Said obelisk is Sydney's true centre – it's the point from where road distances have traditionally been measured.

Nearby is a big anchor, and closer inspection shows it belongs to the Sirius – the largest ship in the First Fleet. The ship got wrecked off Norfolk Island, and the anchor was rescued decades afterwards. The gun in front of the anchor also belonged to the Sirius, and was repurposed as the signal gun at Signal Hill near South Head, telling ships they were close to the entrance of Port Jackson.

The Watson's Bay to Bondi walk

Signal Hill is passed on the way from Watson's Bay to Bondi, along with other oddities such as the Macquarie Lighthouse, and the anchor of the Dunbar – the ship that fell victim to Sydney's deadliest ever wreck. But it's the cumulative whole that's more impressive than individual stops – all crashing surf, majestic sandstone formations, and peaceful clifftop reserves.

It's less well known and more disjointed than the staple Bondi to Coogee Walk, but roughly the same distance, and with far fewer marauding joggers.

The ANZAC Memorial

Well, few people miss it – most will stop to admire the chunky but elegant art deco memorial as they walk through Hyde Park. But not a lot of people realise they can go inside. There's a mini museum in there, with wartime recollections from those who went to fight and those who were left behind. Sweetheart brooches, artificial limbs and emergency telegrams to home add to the poignancy.

But the most heart-in-mouth views come from up the steps. The dome overhead is dotted with gold stars, each representing a volunteer NSW serviceman from World War I. And the jarring centrepiece is George Rayner Hoff's statue of a dead, naked male being held aloft on the shoulders of three women. The statue looks provocatively modern eight decades after being unveiled, and the heavy symbolism strikes home. See anzacmemorial.nsw.gov.au

Elizabeth Farm

Cadmans Cottage in The Rocks is usually billed as Sydney's oldest building, but that's nonsense – Elizabeth Farm in Parramatta was knocked up in 1793 (although modified after that). Now, it serves as a beautifully peaceful museum, with the idea being that you can wander through at will, nosying at documents and furniture belonging to the former owner.

And, while the sprawling gardens are rather lovely, it's the backstory of that owner that makes it worth the visit. John Macarthur was a pioneering farmer who arrived on the Second Fleet, but more importantly, he was a troublesome, conniving pain in the backside who kept getting Governors overthrown. The displays go into a series of tremendous tales – of him having to go back to Britain to be court-martialled for duelling, and using his time there to effectively set up the Australian wool industry – that perk up the history of the early colonial era. See mhnsw.au

The Grotto Point engravings

On the North Shore of Sydney Harbour, Dobroyd Head bulges out into the water. There are some great lookouts here, should you want to stock up on those obligatory harbour photos, but Grotto Point at the western end has a couple of intriguing oddities. The Grotto Point Lighthouse is still a working lighthouse, and a short track branches off to it from the Manly Scenic Walkway.

But sticking to the route from the Spit Bridge to Manly through Sydney Harbour National Park, you'll also come to some exposed stone slabs nearby.

Look carefully at these, and you'll see engravings of small fish, boomerangs and – most notably – a giant kangaroo. Grotto Point is probably the easiest place to see ancient Aboriginal rock art in Australia. See nationalparks.nsw.gov.au

West Head

There are more Aboriginal rock engravings at Red Hands Cave in the West Head section of Ku-Ring-Gai Chase National Park. They're not as easy to get to – this is in the far north of the city. But the looping 4.4 kilometre Aboriginal Heritage Walk is well worth undertaking here. It includes a couple of dainty cove beaches, but the main highlight is the West Head Lookout.

This is probably the best view in Sydney that doesn't include the Harbour Bridge. It takes in Pittwater, the Barrenjoey Peninsula, Broken Bay and the southern beaches of the Central Coast. There's a proper edge of the frontier feel, too. See nationalparks.nsw.gov.au