Lots of cyclists ride in the areas around Watsons Bay, Dover Heights and Vaucluse and why not, the sights up the bay and down the cliffs are fantastic. But its all roads and there are people driving around. To minimise your risk you can ride on a Sunday morning and you can take it easy. Another way is to only ride from Bondi to Watsons Bay and catch the ferry back to Rose Bay or the city. Or see what roads to ride in Paddington.
Waverley to Vaucluse
My trail starts at the beginning of Henrietta St in Bronte and heads across Waverley Park and down a council road into Rose Bay. Downhill is all on Birriga road and you likely will be going close to the speed of the cars anyway. On the way back up the cycle path is well marked on the side of the road with the odd section off road where the corners are tight. Its a good climb. The ride around Royal Sydney golf club into Rose Bay Village is on a tight separated cycle way. Once you are in Rose Bay, the real cyclists will head up New South Head Rd. The other way up steeper hills on back streets is the way I have mapped. At Vaucluse Water tower, its onto the roads.
Here is the black trail from Waverly to Vaucluse >>
From the Water Tower
From the water tower in Vaucluse, I rolled down to Vaucluse House on a really nice winding Hopetown Rd. After riding around Vaucluse house I then headed to Parsley Bay where I should have walked across rather than ride the roads around it. Then I hugged the harbour up to Watsons Bay with a quick trip to a hidden beach called Kutti Beach. I rolled around Watsons Bay and then turned on the turbo and went up the hill to Dunbar Head lighthouse. The best bit was the cliffs around Diamond Bay Reserve.
Very hilly, I did this on my eBike and that was hard enough. Do it on a sunday morning when its quiet. I won’t put this on my Sydney East map as its all roads but here is a separate map of the full trip >>
Shared Path 10%
Busy Roads 40% and not busy 50%
Around the Eastern Suburbs (north end)
Most cyclists just ignore my hesitant ways and head right down to Watsons Bay on the biggest roads, climb up to Dover Heights and ride to Bondi on Military Road. I finally did that this year as piece 6 of my Sydney Jigsaw Puzzle map
Its great fun on a Sunday, you need to be strong as there is 500m of climbing over 35km.
See the trail on the puzzle map in black here >>
Here is sample of what you will see on this roady ride (shown in black on the map above)
The Lanes of Paddington
There are very few actual shared paths in this area but a lot of people ride bicycles and there are a lot of bicycle signs on posts and painted signs on the road. In the end the trails marked are good to get you going and see the area and they mostly run along the contours of the hills. See all the photos here and
Here are the rides on the Sydney Map
A spectacular place that has a few tracks, some hilly