Georges Head to Middle Head Loop
If you’re into military history, you’ll love this walk. But never mind if you’re not because the trail is so beautiful that you’ll love it too. The trail includes the recently completed 3km pathway linking Georges Head with Middle Head–Gubbuh Gubbuh.
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This scenic trail in Mosman combines spectacular harbour views with rare glimpses into Sydney’s military history.
Distance >6km Time 1-2 hours
Level of Difficulty Easy-moderate -
Sweeping views of the entire inner harbour
Fascinating, well sign-posted military history
Plenty of places to stop for refreshment
Headland Park sculpture garden
Native fauna and seasonal wildflowers
Many great places and paths to explore nearby (see list below)
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Dogs on lead are permitted in some areas, prohibited in others
Parking can be limited, particularly on weekends, so if the Gunners Alley carpar is full, there is other parking within Headland Park, some paid, some not. Alternatively, you can usually get a spot on 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 recommended. And pack your snorkel and flippers of you decide to take the side trail down to Chowder Bay.
Getting to Georges Head
As this is a loop trail you can start at either end. I started at Georges Head. You can access Georges Head from Middle Head Rd which branches off Military Road.
If you’re driving in, look for the Headland Park sign at Suakin Drive and turn right. Follow the road to its end where you'll find the small Gunshot Alley car park near a boom gate. Park here in an untimed parking spot (do check signs) and take the short walk past the Gunners Barracks to the headland.
If you’re arriving by public transport, probably the easiest way to get here is to take the ferry from Circular Quay to Mosman Bay Wharf. From there catch the 111 bus that runs up Middle Head Rd. Get off the bus at Markham St and walk a block to the Headland Park entrance and follow the signs to Gunners Barracks down to the headland.
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 map above points to some of the main things to look out for along the way.
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 the 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 are a few steps leading on to the start of trail through Headland Park to Middle Head Rd.
On your left side 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 in a clockwise direction, follow the track past the of 19th century cottages to the 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 story about shell practice gone wrong which resulted in mayhem at North Head’s Quarantine Station.
Inner Middle Head Fort
Remnants of the old tunnel network that sits below the walking path, can be seen clearly when you reach the Outer Middle Head Battery.
This site also features old canons, pits, gun emplacements, ‘tiger cages’ and other structures, all built to protect Sydney from potential invasion.
Return trail
Beginning the return loop now, the trail takes a lower track and alternates between harbour (more great views), and bushland punctuated by the colour and calls of native flora and fauna.
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 they’re optional at this nudist 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.
The path along Chowder Bay Rd passes the old Sergeants’ Mess (now a function centre) and the Harbour Lodge and Land’s Edge building near the end of the road. Here, look for signs to Bungaree Wakway which will take you up through the bush (the steepest section of the walk) and back to Georges Heights.
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.
