To discover a side of Sydney Harbour the tourist crowds rarely find, take this hike from Bradleys Head to Middle Head as it winds along the harbourside.


  • Gorgeous Sydney Harbour views
  • Swimming opportunities at hidden beaches and bays
  • Heritage listed fortification sites
  • Lesser known harbourside bushwalk

Bushwalking Along the Harbour

The Bradleys Head to Middle Head return bushwalk along Sydney Harbour is one of the lesser championed harbourside trails. There’s a plethora to choose from, and this walk via Chowder Bay in the Sydney Harbour National Park is among the best of ‘em. Traditional custodians of this beautiful land are the Gadigal clan of the Eora Nation and we pay our respects to them.

Admittedly, you’ll have the best views of the Sydney Harbour Bridge and Opera House from the start of this hike at Bradleys Head, so this bushwalk really starts off with a bang.


Bradleys Head to Middle Head is a Perfect Harbourside Hike (NSW), Daniel Piggott, Sydney Harbour, Opera House, Harbour Bridge, people, happy

Compulsory harbour shot


After snapping some photos, the bushwalk begins. Relatively quickly, you’ll feel away from the glitz and glamour of Sydney’s main harbourside attractions, and be enjoying the real reason you came to visit. Walking the tranquil trail loaded with idyllic beaches and bays hidden from the usual Sydney crowds.

The first major stop of interest is Taylors Bay. It’s a beautifully secluded and swimmable bay accessible from a set of steps that’s somewhat overgrown. If you can resist the temptation to take a dip so early on in the piece, keep charging towards Chowder Bay.

Opposite this slightly busier bay is the large Clifton Gardens Reserve. A great place to stop for a snack. But don’t take too long, one of the highlights of this walk is right around the corner. 

It’s an area full of fascinating history – the Georges Head Lookout. Not only will you have epic views of South Head and North Head – the gateway to Sydney Harbour – but you’ll have military fortifications from WWII to check out. And for the history buffs, your walk will only get better! 

After enjoying this lookout, continue your walk to Middle Head. Home to heritage listed fortifications with construction dating back to 1801! You’ll really be blown away by the historical sites on offer during this bushwalk. Plus the serene views over the Sydney Harbour are unending over the course of the hike.


Bradleys Head to Middle Head is a Perfect Harbourside Hike (NSW), Daniel Piggott, Sydney Harbour, headland, military fortifications

Heritage-listed fortifications at Middle Head


One last thing before you head back to Bradleys Head. There’s a really stunning beach to visit called Obelisk Beach. Beware, it’s a nudist beach. So if that’s not your cup of tea, then carry on. Otherwise, it’s worth a stop.

The beach is only a short detour from the Middle Head area and is located off Chowder Bay Road. From the roadside, you’ll traverse a tiny set of steps. A small golden sand harbourside beach awaits you. There are some cool rocks off to the left as you enter the beach to explore.


Bradleys Head to Middle Head is a Perfect Harbourside Hike (NSW), Daniel Piggott, Sydney Harbour, Obelisk Beach, nudist beach, rocks

Obelisk Beach


Keep in mind that the trail is fairly narrow from Bradleys Head to Chowder Bay. So it can get overcrowded at peak times during the weekend. So to beat the crowds, make this one an early adventure.

Essential Gear

  • Decent footwear 
  • Sunscreen
  • Sunnies
  • Hat
  • Day backpack
  • Camera
  • Budgie smugglers
  • Towel
  • Flip flops
  • Snacks
  • Water
  • Waterproof/windproof jacket, fleece jacket & waterproof bag cover in winter

How To Get There

Well, there are quite a few options for parking! These are the two options we recommend though:

Option 1: Bradleys Head Car Park

Parking here is the logical choice. But you’re looking at $8/day. Plus, there are only about 20 spaces, so it can fill up quickly on the weekend.

Option 2: Chowder Bay Road Parking next to Obelisk Beach

Under certain circumstances, parking here can be for FREE! If you hold a NSW National Parks All Parks or Multi Parks Pass, you can park for free for up to 4 hours/day. So you better be speed hiking this bushwalk! Otherwise, parking here is $3/hour, to a max of $16/day, increasing to $4/hour, to a max of $20/day on weekends and public holidays. 

There’s less parking here than compared with Bradleys Head so arrive early to avoid disappointment. Middle Head car park is also around the corner but can be a bit exxy. 

If you don’t have a set of wheels, you could always get the ferry to Taronga Zoo from Circular Quay. The walk from Taronga Zoo Wharf to Bradleys Head would be a lovely 1.5km harbourside addition taking only 20 minutes or so.


  • Harbourside bushwalking
  • Swimming at hidden beaches and bays
  • Exploring heritage listed historical sites
  • Plenty of photo ops!

Skill Level


Distance Covered / Elevation Gain / Duration

Approximately 10km / 29m / 3-3.5 hours


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