Georges Head to Middle Head Loop
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This scenic trail in Mosman combines spectacular harbour views with rare glimpses into Sydney’s coastal defence history.
Distance c6km Time 1-2 hours
Steps c10,000
Level of Difficulty Easy-moderate -
Sweeping views of the entire inner harbour and out through the heads
Extensive 19th-century military fortifications and tunnels
Seasonal wildflowers and native birdlife
Cafés and scenic picnic spots along and near the route
Headland Park sculpture garden and heritage buildings
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Dogs are permitted on lead in some sections of Headland Park but prohibited in others - check signage
Parking near Georges Head (Gunshot Alley) is limited on weekends; additional parking is available within Headland Park and along Middle Head Rd.
Start out early if you can - better light for photos and fewer people around.
Wear comfortable shoes with good grip as some sections near the water can be slippery and other areas muddy particularly after rain.
Water, hat, sunscreen and swimmers are recommended. And pack your snorkel and flippers of you decide to take the side trail down to Chowder Bay.
If you’re into military history, you’ll love this walk — but even if you’re not, the setting alone makes it memorable. This harbour headland loop links Georges Head with Middle Head–Gubbuh Gubbuh via a recently completed coastal pathway through Headland Park.
Along the way are sweeping harbour views, bushland tracks and remarkably intact fortifications dating from the 1870s. It’s an easy to moderate walk with plenty to explore, and many opportunities to extend or detour to nearby beaches and parklands.
Getting to Georges Head
As this is a loop, you can start at either end. I started at Georges Head, accessed via Middle Head Rd off Military Road.
If you’re driving, turn at the Headland Park sign on Suakin Drive and follow the road to the small Gunshot Alley car park near the boom gate (check signage for parking limits). From here, walk past Gunners Barracks to the headland.
If you’re arriving by public transport, take the ferry from Circular Quay to Mosman Bay Wharf. From there catch the 111 bus along Middle Head Rd. Leave the bus at Markham St and walk a block to the Headland Park entrance and follow the signs to Gunners Barracks and the headland.
WALKING THE TRAIL
The Georges Head to Middle Head loop walk is approximately 6 kms long and can take anywhere from one hour to several, depending on stops for exploration or diversion. The trail is not a difficult one and the terrain is mostly flat but there is a steep uphill section through bushland at the end.
Georges Head Lookout to Middle Head–Gubbuh Gubbuh
Beginning at the Gunners Barracks, walk down to the Georges Head Lookout to take in the 180-degree views of the harbour and city before wandering down to see remnants of some of Sydney's military fortifications dating back to the 1870s.
View from Georges Head lookout
The Georges Head Battery is one of three old forts you’ll see on this walk, all built for the purpose of defending Sydney’s outer harbour.
The original battery at Georges Head once housed six guns in open circular pits connected by passages and tunnels that led to an underground magazine. The tunnels are generally closed to the public but can be explored on the Tunnels and Gunners Tour which runs on the first Sunday of each month (booking essentials).
Behind the lookout, steps lead into Headland Park and the start of the track toward Middle Head Rd. On the left as you walk, Headland Park opens up to reveal green space with a backdrop of heritage buildings and a sculpture garden that’s worth jumping off the track to see.
Turn right when you get to Middle Head Rd and take the stairway that winds down through native forest to Burnt Orange, a popular local lunch cafe/restaurant and former clubhouse for the Mosman Golf Club (1920s).
Continue down past (the still active) HMAS Penguin and Middle Head Oval toward the headland and the entrance to the Middle Head-Gubbah Gubbah precinct.
Middle Head–Gubbuh Gubbuh
Walking clockwise, follow the track past the of 19th century cottages to the Inner Middle Head Fort.
Inner Middle Head Fort
Gazing out from the remnants of the old fort, you’ll have panoramic views across the inner harbour, from Manly and North Head across to South Head and the eastern suburbs.
Look out for the plaques and signboards that explain some of the workings of the inner fort and battery and reveal some of its more intriguing history, including the infamous shell-practice session gone-wrong, which resulted in damage at North Head’s Quarantine Station.
Further on, remains of the tunnel network are visible near the Outer Middle Head Battery, where cannon, gun pits, emplacements and “tiger cages” remain in place.
Return via Obelisk and Georges Head
The return loop follows a lower coastal track alternating between bushland and harbour views. You’ll pass the long-abandoned 1801 Fort and Obelisk Casemate, with a side trail down to Obelisk Beach — a clothing-optional harbour cove.
You'll pass the long abandoned 1801 Fort and the Obelisk Casemate as you make your way along the coastal track. There’s a trail leading off to Obelisk Beach along this section and don’t worry if you’ve forgotten to bring your swimmers as clothing is optional at this beach 😜.
You can see clearly over to South Head, Neilson Park and the eastern suburbs on the return trail
Continue on to pass over the tunnels of the the Beehive Casemate and on to the Armoured Casemate of the Georges Head Battery with its three-storey tower and gun emplacement. Between the two is the Belvedere lookout, a good place to pause and take in the views of the harbour and ocean out between the heads.
Georges Head Casemate Battery
From the observation tower, turn right to take the steps up to Chowder Bay Rd. Follow the road past the former Sergeants’ Mess and Harbour Lodge to signs for the Bungaree Walkway, which climbs steeply through bush back to Georges Heights and the starting point.
Things to see & do nearby
One of the things I really like about this walk is the location. Mosman is without doubt one of Sydney’s most beautiful suburbs and there are heaps of other things to check out nearby. Some suggestions:
Headland Park picnic area and artist precinct - Just off the track near the start and end of the walk, this grassy part of the park is a great place for a picnic or a stroll among the sculptures in the Headland Artists’ Precinct.
Chowder Bay and Clifton Gardens Reserve - If you have the time, I recommend adding this as a side trail near the end of the walk, especially if you’re walking with children. Accessed via a pathway and steps at the end Chowder Bay Rd, the bay is a beautiful swimming area with calm waters, backing onto a beach and reserve with a great shaded playground, large lawn area, barbecues and seating. The waters of Chowder Bay are home to a great array of marine life so you’ll likely see snorkelers and divers about.
Balmoral Beach - A trip to this gorgeous beach can also be added as a side trail at the point where the first part of the loop path comes out on to Middle Head Rd. Instead of turning right, cross the road and take the (steep) steel staircase down to Balmoral Park and on to the beach. There’s a large playground here too, a netted swimming area and plenty of places to eat.
Taronga Zoo is just a short drive away and always worth a visit
Mosman Village has plenty of cafes, restaurants, and shops for post-walk refreshments or high-end boutique browsing,
Eat & Drink You’re spoilt for choice both on and near the trail. Cafes and restaurants along the walking path include Frenchy's and Burnt Orange and the Gunners Barracks for high tea (a bit posh so perhaps best enjoyed after a shower). And not far off the track are others including Ripples at Chowderbay and The Boathouse or Pasture in Balmoral where there are many more.
Other harbour walks - The Taronga to Balmoral Walk crosses the path of this one and the start of the Spit to Manly Walk is not far away. Both walks are around 10km in length and worth taking your time over, so perhaps best saved for another day.
