Score: 8.5/10.
Shorter ride, great tunnels, caves and playgrounds. Fish and chips to end the day!
Star Rating For Difficulty (out of 5): 
2 star because of the hill up Middle Head Rd to Georges Heights.
Notable Sites, Cafés, and Playgrounds Along the Way:
This is a ride to explore history and play around.
Initially ride towards the dead end above Clifton Gardens. The views from Darling Point to North Head are great. It’s a nice spot to soak up all the activity on the water and chat a little.
From there ride to Inner Middle Head Battery. It has great views from the Spit Bridge to Manly and out the heads. It is a great foretaste of the military relics to come. Then backtrack a little to Middle Head itself, apart from the great views, there is so much to explore there. Put the bikes down or securely chain them and explore the tunnels, trenches, gun turntables etc… We then play tip hide and seek (like we do at Strickland House Reserve, on the other side of the harbour on our ride from Wollstonecraft to Watson’s Bay). This can be played for a good hour. There are many great hiding places and all within earshot.
It’s then up the hill of Middle Head Rd which is a solid hill, but in the easiest gear a good primary aged rider can get up it. We like to stop at Frenchy’s café for an ice block, a drink or some food. The kids quite like riding their bikes around the grass just nearby here and to the concrete pad below. From there it’s through Georges Heights, Rawson Oval, but then to the next treat – to again play hide-n-seek tip at the military fortifications at George’s Head Lookout just past “Gunners Barracks”. As opposed to the (mostly) open air tunnels at Middle Head, most of these tunnels are underground and are dark (some very dark), it makes for much running and joyful screaming. Like Middle Head, be prepared for another good hour of fun here and perhaps have a snack on under a tree on the grass soaking up the sights and sounds of Sydney Harbour.
Next go down to Balmoral, ride around the bike track around the oval. There is some fitness equipment there and sometimes the kids like to play, hang and swing on them. But one of the great attractions for the kids down here is Balmoral Beach Playground. This is a great little playground (and yes, we play hide-n-seek tip here too 😊). Nearby take your pick for coffee and a snack, but The Boathouse Balmoral Beach and The Balmoral Beach Kiosk are both very good options.
We ride slowly around the ‘back’ streets of Balmoral, enjoy looking at the houses, and then back down the Esplanade (on the footpath) to our favourite climbing tree – the Moreton Bay Fig across the road from Bottom of the Harbour where we like to end the day with calamari and chips.
Parking & Toilets
To avoid the kids riding back up from Balmoral, I actually parked initially near the end of Chowder Bay Rd and then took the car down to Balmoral. So there are two parking places and this is not an out and back ride (unless you want to ride with your kids back up Coronation Ave Balmoral (a hard way to end the day, and a way to ramp this up to a 4 star difficulty rating).
Toilets:
Middle Head Oval (just near the roundabout)
Georges Heights
Balmoral Oval
Balmoral Baths
Balmoral Esplanade
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-Lachlan Soper