Middle Harbour is the body of water bounded by the Roseville Bridge, Northbridge, The Spit Bridge and surrounded by suburbs like Seaforth, Forestville, Castle Cove, Castlecrag, and Cremorne. My ride plan was simply to loop the Harbour, staying close as possible to water views. Starting near Seaforth, I headed north-west via the dirt track that runs alongside the Wakehurst Parkway then followed the pipeline to Warringah Road and Roseville.

Everyone in Sydney has driven over the Roseville Bridge but few venture underneath. Davidson Park is part of the Garigal National Park and is a delightful riverside picnic area and marina. At the north end of the Park you’ll find the Lyrebird Trail, a couple of kilometers of bush riding amidst nature.

If you have ever wondered what is under that massive chunk of concrete, this is how it looks; makes you feel small.

A cyclepath crosses the bridge which has great views over the Park. At the other end is an underpass which leads back to the Middle Harbour suburbs.

The legendary Innisfallen Castle has been on my must-see list for a long time. Built in 1805 by an early Speaker of the NSW Parliament, the heritage-listed castle is named in honour of an abbey in Ireland; very impressive it is.

The other must-see on this ride was the famous 1892-built Northbridge, after which the suburb was named. You cannot appreciate its beauty just driving across; it’s well worth taking some time walking over it and enjoying the views.

From Northbridge, it’s a winding maze of hilly streets behind Neutral Bay and Mosman, then back to The Spit Reserve. Good to be at water-level again.

The final leg takes me across The Spit Bridge, then up to Seaforth for one of the best panoramic views in Sydney.

A couple of points: this ride was very hilly and an eBike is essential. A lot of time was spent going into suburbs like Castle Cove and Castlecrag, then retreating because they are peninsulas. Also the Harbour views are more like glimpses because in this area properties block most of the access. At 55kms and a bit under four hours, it was a very interesting ride but not one I would do again.